2-Pyridinecarboxaldehyde (Picolinaldehyde) [C6H5NO] [CAS 1121-60-4; InChIKey CSDSSGBPEUDDEE- by Asch

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Date

115 reactions in Reaxys

2018-04-04 14h:01m:42s (UTC)

N O

1. Query

Search as: As drawn AND (IDE.XRN=105341)

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N OH

Rx-ID: 45112 View in Reaxys 1/115 Yield 99 %

Conditions & References With sodium hypochlorite, β-cyclodextrin in water, Time= 1h, T= 50 °C Ji, Hong-Bing; Shi, Dong-Po; Shao, Ming; Li, Zhong; Wang, Le-Fu; Tetrahedron Letters; vol. 46; nb. 14; (2005); p. 2517 2520 View in Reaxys

99.1 %

With tert.-butylhydroperoxide, V/SiO2 in decane, tert-butyl alcohol, Time= 5h, T= 25 °C Rout, Laxmidhar; Nath, Pinku; Punniyamurthy, Tharmalingam; Advanced Synthesis and Catalysis; vol. 349; nb. 6; (2007); p. 846 - 848 View in Reaxys

> 99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 12h, T= 75 °C , p= 760.051Torr Zhang, Xiaowei; Dong, Wenjun; Luan, Yi; Yang, Mu; Tan, Li; Guo, Yangguang; Gao, Hongyi; Tang, Yinhai; Dang, Rui; Li, Jie; Wang, Ge; Journal of Materials Chemistry A; vol. 3; nb. 8; (2015); p. 4266 - 4273 View in Reaxys

> 99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium carbonate in acetonitrile, Time= 6h, T= 75 °C Li, Jie; Gao, Hongyi; Tan, Li; Luan, Yi; Yang, Mu; European Journal of Inorganic Chemistry; vol. 2016; nb. 30; (2016); p. 4906 - 4912 View in Reaxys

99.9 %

With aluminum oxide, bis(2,2'-bipyridine)([2,2'-bipyridine]-5,5'-dicarboxylic acid)ruthenium(II) dichloride, oxygen in acetonitrile, Time= 12h, p= 750.075Torr , Irradiation, Reagent/catalyst Leow, Wan Ru; Ng, Wilson Kwok Hung; Peng, Tai; Liu, Xinfeng; Li, Bin; Shi, Wenxiong; Lum, Yanwei; Wang, Xiaotian; Lang, Xianjun; Li, Shuzhou; Mathews, Nripan; Ager, Joel W.; Sum, Tze Chien; Hirao, Hajime; Chen, Xiaodong; Journal of the American Chemical Society; vol. 139; nb. 1; (2017); p. 269 - 276 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 12h, T= 60 °C , p= 760.051Torr Li, Ruilian; Zhao, Jian; Yang, Fengxia; Zhang, Yingchao; Ramella, Daniele; Peng, Yu; Luan, Yi; RSC Advances; vol. 7; nb. 81; (2017); p. 51142 - 51150 View in Reaxys

99 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C12H8Cl3FeN2O4Zr4, oxygen, sodium nitrite in acetonitrile, Time= 12h, T= 20 °C , p= 760.051Torr Shu, Xin; Yu, Ying; Jiang, Yi; Luan, Yi; Ramella, Daniele; Applied Organometallic Chemistry; vol. 31; nb. 12; (2017); Art.No: E3862 View in Reaxys

98 %

With oxygen, Nafion polymer anchored ruthenium oxide pyrochlore composite in acetone, Time= 6h, T= 20 °C , p= 760.051Torr Venkatesan; Kumar, A. Senthil; Zen; Tetrahedron Letters; vol. 49; nb. 28; (2008); p. 4339 - 4341 View in Reaxys

98 %

With manganese(II) nitrate, C70H128N16O4, oxygen, cobalt(II) nitrate in acetic acid, Time= 1.5h, T= 40 °C , Mechanism Minisci, Francesco; Recupero, Francesco; Rodino, Marianna; Sala, Massimiliano; Schneider, Armin; Organic Process Research and Development; vol. 7; nb. 6; (2003); p. 794 - 798 View in Reaxys

98 %

9 : 2.2 General procedure for the dehydrogenation of benzylic alcohols using Ag/ZnO nanoparticles General procedure: A mixture of alcohol (1 mmol), KOH (1 mmol), and 0.005 g Ag/ZnO nanoparticles (2) (containing 8×10−5g Ag) in toluene (2 mL) was stirred at 100 °C for the appropriate time. The reaction was monitored by thin layer chromatography

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(TLC) or GC. After completion of the reaction, the reaction mixture was diluted with EtOAc and centrifuged to remove the catalyst. The filtrate was extracted with water, the organic layer dried over CaCl2 and evaporated under reduced pressure. The resulting product was purified by column chromatography on silica-gel to afford the pure product. All compounds are known and were characterized by comparison of their physical and spectroscopic data with the already described in the literature. With potassium hydoxide in toluene, Time= 4h, T= 100 °C Hosseini-Sarvari, Mona; Ataee-Kachouei, Tahereh; Moeini, Fatemeh; Materials Research Bulletin; vol. 72; (2015); p. 98 105 View in Reaxys 97 %

With lt;MoO(O2)2(C5H4N(O)COO)gt;-Bu4N+ (MoO5PICO) in dichloromethane, Time= 48h, T= 50 °C Campestrini, Sandro; Furia, Fulvio Di; Modena, Giorgio; Journal of Organic Chemistry; vol. 55; nb. 11; (1990); p. 3658 3660 View in Reaxys

96 %

With aluminium trichloride, 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate in acetonitrile, Time= 2.5h, Heating Hajipour, Abdol R.; Bagheri, Hamid R.; Ruoho, Arnold E.; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 44; nb. 3; (2005); p. 577 - 580 View in Reaxys

96 %

With VO(O-i-Pr)(8-hydroxyquinolinate)2, triethylamine in 1,2-dichloro-ethane, Time= 24h, T= 80 °C Hanson, Susan K.; Wu, Ruilian; Silks, L. A. Pete; Organic Letters; vol. 13; nb. 8; (2011); p. 1908 - 1911 View in Reaxys

96 %

8 : Example 8: Strengthening of Oxidative Oxidation of 2-pyridinecarboxaldehyde by Perfluorooctyl Sulfate (1) In a 50 ml flask, 0.218 g (2 mmol) of 2-(hydroxymethyl)pyridine, 3 ml of deionized water, 0.06 g (0.12 mmol) of sodium perfluorooctylsulfate, Stirring for 10 min to dissolve the surfactant,stand-by. (2) A solution of 0.0244 g (0.2 mmol) of 4-dimethylaminopyridine, 0.0362 g (0.1 mmol) of Cu(OTf)2, 4.5 ml of deionized water was added to a 50 ml flask, and the solid was dissolved in a nitrogen atmosphere, Stop the nitrogen, To obtain complex solution, stand-by. (3) 4.5 ml of the complex solution obtained in step (2) and 2.5 ml of a solution of 2-azabicycloadamantane-nitrogen oxide (0.04 M) was added to the flask (1) In the air atmosphere, 20 deg C conditions for 5h, After the reaction, The reaction solution was subjected to liquid separation, The resulting lower oil phase was washed with saturated sodium chloride solution, Dried over anhydrous sodium sulfate, To obtain an oxidation product of 2-pyridinecarboxaldehyde 0.205 g, Yield 96percent GC content of 98percent; The resulting aqueous layer of the upper layer was extracted with ether, The solvent is distilled off to recover the fluorosurfactant. With dmap, sodium perfluorooctane sulphonate, copper(II) bis(trifluoromethanesulfonate) in water, Time= 5h, T= 20 °C Patent; Zhejiang University of Technology; Wang, Jianli; Chen, Xianbo; Zhang, Qi; (10 pag.); CN106316730; (2017); (A) Chinese View in Reaxys

95 %

With oxygen in toluene, Time= 6h, T= 80 °C Kantam, M. Lakshmi; Pal, Ujjwal; Sreedhar; Bhargava, Suresh; Iwasawa, Yasuhiro; Tada, Mizuki; Choudary; Advanced Synthesis and Catalysis; vol. 350; nb. 9; (2008); p. 1225 - 1229 View in Reaxys

94 %

With 1-decyl-4-aza-1-azoniabicyclo[2.2.2]octane chlorochromate, Time= 0.1h, T= 20 °C Hajipour; Bagheri; Ruoho; Russian Journal of Organic Chemistry; vol. 42; nb. 6; (2006); p. 844 - 848 View in Reaxys

94 %

With oxygen in o-xylene, Time= 7h, T= 119.84 °C Yoshida, Akihiro; Takahashi, Youichi; Ikeda, Tsuyoshi; Azemoto, Kazuki; Naito, Shuichi; Catalysis Today; vol. 164; nb. 1; (2011); p. 332 - 335 View in Reaxys

94 %

1 : Example 2 (A) 2-pyridinemethanol was dissolved in methylene chloride and stirred uniformly, wherein the concentration of 2-pyridinemethanol was 0.4 g / mL;

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(B) adding the MnO2 composite catalyst powder into the solution in the step (a), uniformly mixing and reacting at the temperature of 40 DEG C for 3.5 hours, wherein the concentration of the MnO2 composite catalyst powder is 0.05 g / mL; (C) cooling the reaction solution to room temperature after the completion of the refluxing reaction, and then separating the MnO2 composite catalyst powder from the reaction solution by a magnetic separation method to obtain a methylene chloride reaction solution; (D) distilling the methylene chloride reaction solution obtained in step (c) at atmospheric pressure to recover methylene chloride, and then distilling under a high vacuum under reduced pressure to collect fractions of 63 to 65 ° C / 1.73 kPa to obtain 2- Pyridine formaldehyde. The yield of 2-pyridinecarbaldehyde was 94percent in this example, and its purity was 99.3percent by gas chromatographic analysis. The MnO2 composite catalyst powder obtained after magnetic separation was stable and could be used in the preparation of 2-pyridinecarbaldehyde. With MnO2 composite catalyst in dichloromethane, Time= 3.5h, T= 40 °C , Concentration, Temperature Patent; Anhui Xingyu Chemical Co., Ltd.; Zhang, Kuanyu; Jin, Wenyi; Ding, Liang; Li, Jing; Zhang, Sheng; (9 pag.); CN105601559; (2016); (A) Chinese View in Reaxys 94 %

2.3. Procedure for oxidation of benzylic alcohols by [CuNi(-OAc)(-OH)(-OH2)(bpy)2](ClO4)2 To a mixture of benzyl alcohol (0.5 mL, 4.64 mmol) and 15percent aqueous hydrogen peroxide(1.1 mL, 4.85 mmol), the catalyst [CuNi(-OAc)(-OH)(-OH2)(bpy)2](BF4)2 (8 mg, 0.01 mmol)was added and stirred at 70 °C for 5 h. The organic and aqueous phase were separated by aseparating funnel and then puried by column chromatography to aord benzaldehyde.The identity of the benzaldehyde was ascertained by comparison with authentic sampleusing IR, 1H NMR, and 13C NMR. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [CuNi(-OAc)(μ-OH)(μ-OH2)(bpy)2](ClO4)2, dihydrogen peroxide in water, Time= 1h, T= 70 °C Lal, Ram A.; Kumar, Arvind; Syiemlieh, Ibanphylla; Kurbah, Sunshine D.; Journal of Coordination Chemistry; vol. 70; nb. 15; (2017); p. 2722 - 2735 View in Reaxys

93 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, tert.-butylnitrite, oxygen, acetic acid in 1,2-dichloro-ethane, Time= 3h, p= 1500.15Torr , Autoclave, Heating He, Xijun; Shen, Zhenlu; Mo, Weimin; Sun, Nan; Hu, Baoxiang; Hu, Xinquan; Advanced Synthesis and Catalysis; vol. 351; nb. 1-2; (2009); p. 89 - 92 View in Reaxys

92 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, 2,2'-[1,2-ethanediylbis(iminomethanediyl)]diphenol copper(2+) salt, oxygen in toluene, Time= 26h, T= 100 °C , atmospheric pressure Velusamy, Subbarayan; Srinivasan, Arumugam; Punniyamurthy; Tetrahedron Letters; vol. 47; nb. 6; (2006); p. 923 - 926 View in Reaxys

91 %

With selenium(IV) oxide, bis-{4-methoxy-phenyl}-selenoxyde in 1,4-dioxane, Time= 24h, Heating Ogura, Fumio; Otsubo, Tetsuo; Ariyoshi, Kimio; Yamaguchi, Hachiro; Chemistry Letters; (1983); p. 1833 - 1834 View in Reaxys

91 %

With bis(acetylacetonate)oxovanadium, oxygen, 1-butyl-3-methylimidazolium Tetrafluoroborate, 1,4-diaza-bicyclo[2.2.2]octane, Time= 6h, T= 100 °C , p= 760Torr Jiang, Nan; Ragauskas, Arthur J.; Tetrahedron Letters; vol. 48; nb. 2; (2007); p. 273 - 276 View in Reaxys

90 %

With Mn3O4 in N,N-dimethyl-formamide, Time= 4h, T= 80 °C Sun, Hua-Yin; Hua, Qing; Guo, Feng-Feng; Wang, Zhi-Yong; Huang, Wei-Xin; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 569 - 573 View in Reaxys

90 %

With dihydrogen peroxide in water, acetonitrile, Time= 1.66667h, T= 90 °C Fazaeli, Razieh; Aliyan, Hamid; Poorgholam, Mohammad Reza; Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry; vol. 42; nb. 6; (2012); p. 805 - 810

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View in Reaxys 89 %

Experimental Procedures for oxidation of Various alcohols: General procedure: A CH3CN solution of alcohol (1 mmol), ZnBr2 (45 mg, 0.2 mmol), and chloramine-T (282 mg, 1 mmol) was placed in a three necked flask with a reflux condenser. After the mixture was stirred under reflux for 1.5-5 h. After cooling to room temperature, the solution was quenched by adding water and the resulting mixture was extracted with AcOEt. Removal of the solvent under reduced pressure gave the crude product, which was purified by column chromatography on silica gel to give the corresponding carbonyls. With chloroamine-T, zinc dibromide in acetonitrile, Time= 2h, Reflux Wang, Peng; Cai, Jin; Yang, Jiabin; Sun, Chunlong; Li, Lushen; Hu, Huayou; Ji, Min; Tetrahedron Letters; vol. 54; nb. 6; (2013); p. 533 - 535 View in Reaxys

89 %

2.2 Catalytic reaction General procedure: In a typical experiment, 4-methoxybenzyl alcohol (12μL, 0.1mmol), Cu-FMOF (11.3mg, 10mmol percent), TEMPO (7.8mg, 0.05mmol) and NaCO3 (10.6mg, 0.1mmol) in 1mL of air saturated acetonitrile were taken in a 15-mL threenecked round-bottom flask. The solution was magnetically stirred for 16h at 75°C under air atmosphere. The progress of the reaction was monitored via gas chromatography (Shimadzu GC-2010AF) involving a Chromopak capillary column and flame ionization detector. The products were further confirmed by using gas chromatography–mass spectroscopy (GC–MS) (Shimadzu GCMS-2010). The concentrations of 4-methoxybenzyl alcohol and 4-methoxybenzylaldehyde were calibrated by external standard method with standard samples (see Fig. S1). With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, {[Cu2(1,2-benzenedicarboxylate)2(1,4-bis(1,2,4-triazol-1-ylmethyl)-2,3,5,6-tetrafluorobenzene)2]·3H2O}n, sodium carbonate in acetonitrile, Time= 16h, T= 75 °C Chen, Sheng-Chun; Lu, Sheng-Nan; Tian, Feng; Li, Nan; Qian, Han-Yu; Cui, Ai-Jun; He, Ming-Yang; Chen, Qun; Catalysis Communications; vol. 95; (2017); p. 6 - 11 View in Reaxys

89 %

General procedure: Benzyl alcohol (0.05g, 0.5mmol), was added to a mixture of 15percent H2O2 (0.3 g, 8.83mmol), complex [MoO2)2(slsch)(H2O)2] (0.01g, 0.017mmol) in acetonitrile solution in 50mL round bottom flask. The mixture was first stirred at ambient temperature for 20mins and then the temperature was raised to 70°C for 2h. The crude product was separated by a separating funnel and dried over anhydrous sodium sulfate. The oxidized product was purified by column chromatography to afford benzaldehyde. The isolated product was ascertained by comparison with the authentic sample using 1H and 13C NMR spectroscopies. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C18H18Mo2N4O10, dihydrogen peroxide in acetonitrile, Time= 3h, T= 20 - 70 °C Kurbah, Sunshine Dominic; Kumar, Arvind; Syiemlieh, Ibanphylla; Asthana; Lal, Ram A.; Inorganic Chemistry Communications; vol. 86; (2017); p. 39 - 43 View in Reaxys

88 %

With oxygen, polyaniline supported VO(acac)2 in toluene, Time= 12h, T= 100 °C Reddy, Sabbasani Rajasekhara; Das, Subhabrata; Punniyamurthy; Tetrahedron Letters; vol. 45; nb. 18; (2004); p. 3561 3564 View in Reaxys

88 %

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in neat (no solvent), Time= 2.5h, T= 20 °C , Milling Achar, Tapas Kumar; Maiti, Saikat; Mal, Prasenjit; RSC Advances; vol. 4; nb. 25; (2014); p. 12834 - 12839 View in Reaxys

88 %

With oxygen in toluene, T= 80 °C , p= 8250.83Torr , Inert atmosphere Mannel, David S.; Stahl, Shannon S.; Root, Thatcher W.; Organic Process Research and Development; vol. 18; nb. 11; (2014); p. 1503 - 1508 View in Reaxys

87 %

With potassium permanganate in various solvent(s), Time= 2h, T= 20 °C Kumar, Anil; Jain, Nidhi; Chauhan; Synthetic Communications; vol. 34; nb. 15; (2004); p. 2835 - 2842

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View in Reaxys 87 %

With iron(III) chloride, 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy, oxygen, acetic acid, sodium nitrite in 1,2-dichloroethane, Time= 5h, T= 50 °C , p= 3000.3Torr , Autoclave Yin, Weili; Chu, Changhu; Lu, Qiongqiong; Tao, Jianwei; Liang, Xinmiao; Liu, Renhua; Advanced Synthesis and Catalysis; vol. 352; nb. 1; (2010); p. 113 - 118 View in Reaxys

87 %

With [Imim-PEG1000-TEMPO][CuCl2 -] in neat (no solvent), Time= 16h, T= 60 °C , Green chemistry Wang, Zhao-Gang; Jin, Yong; Cao, Xiao-Hua; Lu, Ming; New Journal of Chemistry; vol. 38; nb. 9; (2014); p. 4149 - 4154 View in Reaxys

87 %

With (1,3-bis(2,6-di-iso-propylphenyl)-4,5-dihydroimidazol-2-ylidene) copper chloride, oxygen, potassium hydoxide in dichloromethane, Time= 12h, T= 20 °C , Molecular sieve Zhan, Le-Wu; Han, Lei; Xing, Ping; Jiang, Biao; Organic Letters; vol. 17; nb. 24; (2015); p. 5990 - 5993 View in Reaxys

86 %

With 2-azaadamantane-N-oxyl, oxygen in aq. acetate buffer, Time= 12h, T= 20 °C , pH= 4.5, Green chemistry, Enzymatic reaction, Reagent/catalyst, chemoselective reaction Zhu, Chenjie; Zhang, Zhi; Ding, Weiwei; Xie, Jingjing; Chen, Yong; Wu, Jinglan; Chen, Xiaochun; Ying, Hanjie; Green Chemistry; vol. 16; nb. 3; (2014); p. 1131 - 1138 View in Reaxys

86 %

With C30H24AgBr4N8 (1+)*AgBr2 (1-), N-benzyl-trimethylammonium hydroxide in toluene, Time= 12h, T= 20 °C , Molecular sieve, Schlenk technique Han, Lei; Xing, Ping; Jiang, Biao; Organic Letters; vol. 16; nb. 13; (2014); p. 3428 - 3431 View in Reaxys

86 %

Oxidation process of alcohols General procedure: In a typical process, benzyl alcohol (10 mmol), [PEO-didodecylimidazolium]3[PW12O40]2 (0.05 mol percent), 30 percent aq H2O2 (20 mmol) were then added. The mixture was stirred and under room temperature. The progress of the reaction was monitored by TLC with samples taken periodically. After completion of reaction, the mixture was extracted with ether for three times. The organic layer was dried over anhydrous MgSO4 and evaporated under reduced pressure.The product was analyzed by HPLC and purified by column chromatograph to give benzaldehyde (98 percent yield). The next run was performed under identical reaction conditions. With dihydrogen peroxide in water, Time= 16h, T= 20 °C , Green chemistry Wang, Zhao-Gang; Yang, Yao; Cao, Xiao-Hua; Lu, Ming; Journal of the Iranian Chemical Society; vol. 12; nb. 10; (2015); p. 1765 - 1770 View in Reaxys

85 %

With silica gel, 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate in dichloromethane, Ambient temperature Kernag, Casey A.; Bobbitt, James M.; McGrath, Dominic V.; Tetrahedron Letters; vol. 40; nb. 9; (1999); p. 1635 - 1636 View in Reaxys

85 %

With 1,4-diaza-bicyclo[2.2.2]octane, [bmim]PF6, oxygen, vanadyl acetylacetonate, Time= 12h, T= 95 °C , p= 760.051Torr Jiang, Nan; Ragauskas, Arthur J.; Journal of Organic Chemistry; vol. 72; nb. 18; (2007); p. 7030 - 7033 View in Reaxys

85 %

With oxygen in ethanol, Time= 30h, T= 80 °C , p= 750.075Torr Mao, Fei; Qi, Zhengliang; Fan, Haipeng; Sui, Dejun; Chen, Rizhi; Huang, Jun; RSC Advances; vol. 7; nb. 3; (2017); p. 1498 - 1503 View in Reaxys

84%

With potassium carbonate in water, Time= 4h, T= 90 °C Pourjavadi, Ali; Habibi, Zahra; Applied Organometallic Chemistry; vol. 31; nb. 11; (2017); Art.No: E3783

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View in Reaxys 83 %

With Fe3O4/SiO2 Magnetic nanoparticles coated carboxymethyl-β-CD in water, Time= 2h, T= 50 °C , chemoselective reaction Zhu, Jie; Wang, Peng-Cheng; Lu, Ming; Journal of the Brazilian Chemical Society; vol. 24; nb. 1; (2013); p. 171 - 176 View in Reaxys

82 %

With oxygen in toluene, Time= 26h, T= 110 °C Kantam, M. Lakshmi; Yadav, Jagjit; Laha, Soumi; Sreedhar, Bojja; Bhargava, Suresh; Advanced Synthesis and Catalysis; vol. 350; nb. 16; (2008); p. 2575 - 2582 View in Reaxys

81 %

With 1-(benzoylamino)-3-methylimidazolium chlorochromate in dichloromethane, Time= 8h, Heating Martinez, Yolanda; De Las Heras, Maria A.; Vaquero, Juan J.; Garcia-Navio, Jose L.; Alvarez-Builla, Julio; Tetrahedron Letters; vol. 36; nb. 46; (1995); p. 8513 - 8516 View in Reaxys

81 %

With sulfuric acid, oxygen, sodium nitrite in tetrachloromethane, cyclohexane, Time= 24h, T= 60 °C , Ionic liquid Zhu, Jie; Wang, Peng-Cheng; Ming, Lu; Synthetic Communications; vol. 43; nb. 14; (2013); p. 1871 - 1881 View in Reaxys

81 %

With titanium(IV) oxide, oxygen, Time= 6h, T= 29.84 °C , p= 760.051Torr , Sealed tube, Irradiation Vadakkekara, Raji; Biswas, Abul Kalam; Sahoo, Tapan; Pal, Provas; Ganguly, Bishwajit; Ghosh, Subhash Chandra; Panda, Asit Baran; Chemistry - An Asian Journal; vol. 11; nb. 21; (2016); p. 3084 - 3089 View in Reaxys

80 %

With oxygen, potassium carbonate, vanadia in toluene, Time= 24h, T= 100 °C Velusamy, Subbarayan; Punniyamurthy; Organic Letters; vol. 6; nb. 2; (2004); p. 217 - 219 View in Reaxys

75 %

With potassium bromate, zirconium(IV) oxychloride in acetonitrile, Time= 0.42h, Heating Shirini, Farhad; Zolfigol, Mohammad Ali; Mollarazi, Esmail; Synthetic Communications; vol. 35; nb. 11; (2005); p. 1541 1545 View in Reaxys

73 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, cesium hydroxide, {[(2-(sulfonylquinlium-8-yloxy)phthalic acid-2H)2Cu4(4,4β-bipyridine)4]·2H2O}n·2nH2O in acetonitrile, Time= 12h, T= 80 °C Feng, Xun; Xu, Chen; Wang, Zhi-Qiang; Tang, Si-Fu; Fu, Wei-Jun; Ji, Bao-Ming; Wang, Li-Ya; Inorganic Chemistry; vol. 54; nb. 5; (2015); p. 2088 - 2090 View in Reaxys

72 %

With oxygen, polyaniline-supported MoO2(acac)2 in toluene, Time= 20h, T= 100 °C Velusamy, Subbarayan; Ahamed, Muneer; Punniyamurthy; Organic Letters; vol. 6; nb. 26; (2004); p. 4821 - 4824 View in Reaxys

72 %

General procedure for the Swern-type oxidation reaction General procedure: A solution of DMSO (3.0 mmol) in CH2Cl2 (2.0 mL) was added toa solution of 1 (1.2 mmol) in CH2Cl2 (5.0 mL) at 30 C, and themixture was stirred for 20 min at the same temperature. The alcoholsubstrate (1.0 mmol) was added, and the mixture was stirredfor another 20 min before the dropwise addition of Et3N(3.0 mmol). The mixture was subsequently left to warm to room temperature (20 min) and concentrated under reduced pressure.The product was isolated by flash column chromatography. Stage 1: With 7,7-dichlorocyclohepta-1,3,5-triene in dichloromethane, dimethyl sulfoxide, Time= 0.333333h, T= -30 °C , Inert atmosphere, Swern Oxidation Stage 2: With triethylamine in dichloromethane, dimethyl sulfoxide, Time= 0.333333h, T= -30 - 20 °C , Inert atmosphere, Swern Oxidation Nguyen, Thanh Vinh; Hall, Michael; Tetrahedron Letters; vol. 55; nb. 50; (2014); p. 6895 - 6898

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View in Reaxys 71 %

With 1,4-diaza-bicyclo[2.2.2]octane, 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl, oxygen, 1,3-di(4-pyridyl)propane, copper(II) perchlorate in dimethyl sulfoxide, Time= 2h, T= 20 °C , p= 760Torr Jiang, Nan; Ragauskas, Arthur J.; Journal of Organic Chemistry; vol. 71; nb. 18; (2006); p. 7087 - 7090 View in Reaxys

70 %

With strontium manganate, oxygen in toluene, Time= 24h, T= 79.84 °C Kawasaki, Shuma; Kamata, Keigo; Hara, Michikazu; ChemCatChem; vol. 8; nb. 20; (2016); p. 3247 - 3253 View in Reaxys

65 %

With (6,8,15,17-tetramethyl-7H,16H-5,9,14,18-tetraaza-dibenzo[b,i]-cyclotetradecenato(2-)-k(4)-N,N',N'',N''')nickel(II), sodium tbutanolate in 5,5-dimethyl-1,3-cyclohexadiene, Time= 7h, T= 85 °C , Inert atmosphere, Schlenk technique, Sealed tube Parua, Seuli; Das, Siuli; Sikari, Rina; Sinha, Suman; Paul, Nanda D.; Journal of Organic Chemistry; vol. 82; nb. 14; (2017); p. 7165 - 7175 View in Reaxys

62 %

With 2-Picolinic acid, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, manganese (II) nitrate tetrahydrate Lagerblom, Kalle; Lagerspets, Emi; Keskiväli, Juha; Cook, Chris; Ekholm, Filip; Parviainen, Arno; Repo, Timo; ChemCatChem; vol. 9; nb. 20; (2017); p. 3880 - 3887 View in Reaxys

61 %

With potassium permanganate, Tris(3,6-dioxaheptyl)amine in dichloromethane, Time= 2.25h, Ambient temperature McKillop, Alexander; Mills, Lester S.; Synthetic Communications; vol. 17; nb. 6; (1987); p. 647 - 656 View in Reaxys

60 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, {[Cu(BTPMPA)(OH2)(OTf)]OTf}, oxygen, potassium carbonate in toluene, acetonitrile, Time= 20h, T= 27 °C Dharmalingam, Sivanesan; Koo, Eunhae; Yoon, Sungho; Park, Gyoosoon; Bulletin of the Korean Chemical Society; vol. 35; nb. 3; (2014); p. 715 - 720 View in Reaxys

52 %

With manganese(IV) oxide in dichloromethane, Time= 5h, Ambient temperature Aoyama, Toyohiko; Sonoda, Naoko; Yamauchi, Mariko; Toriyama, Kyoko; Anzai, Masahiro; Ando, Akira; Shioiri, Takayuki; Synlett; nb. 1; (1998); p. 35 - 36 View in Reaxys

41.5 %

With tert.-butylhydroperoxide, Time= 16h, T= 70 °C , Catalytic behavior Zhang, Yuecheng; Sun, Xiaochen; Zhang, Hongyu; Zhao, Jiquan; Applied Organometallic Chemistry; vol. 30; nb. 8; (2016); p. 645 - 652 View in Reaxys

40 %

With (carbonyl)chloro(hydrido)tris(triphenylphosphine)ruthenium(II), oxygen in toluene, Time= 24h, T= 110 °C , p= 760.051Torr , Molecular sieve, Sealed tube Ray, Ritwika; Chandra, Shubhadeep; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemistry - A European Journal; vol. 22; nb. 26; (2016); p. 8814 - 8822 View in Reaxys

38 %

With potassium osmate(VI) dihydrate, potassium carbonate, potassium hexacyanoferrate(III) in water, acetonitrile, Time= 10h, T= 60 °C , chemoselective reaction Fernandes, Rodney A.; Bethi, Venkati; RSC Advances; vol. 4; nb. 76; (2014); p. 40561 - 40568 View in Reaxys

35 %

With dicarbonyl(cyclopentadienyl)iron(II) chloride, sodium hydride in toluene, Time= 20h, Reflux, Inert atmosphere, Schlenk technique, Catalytic behavior, Reagent/catalyst

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Kamitani, Masahiro; Ito, Masaki; Itazaki, Masumi; Nakazawa, Hiroshi; Chemical Communications; vol. 50; nb. 59; (2014); p. 7941 - 7944 View in Reaxys 21 %

Oppenauer Oxidation of Alcohols Using In(i-OPr)3; General Procedure General procedure: To a screw tube in a glovebox was added In(Oi-Pr)3 (29.2 mg, 0.1 mmol). The tube was then sealed and removed from the glovebox, and CHCl3 (1 mL), alcohol (0.5 mmol), and pivalaldehyde (280 μL, 2.5 mmol) were added under N2 in this order. After stirring the mixture at r.t. for 3 h, H2O (1.0 mL) was added to the reaction mixture, which was then extracted with EtOAc. The organic phase was dried (Na2SO4), and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (Table 2 and Scheme 2). With indium isopropoxide, pivalaldehyde in chloroform, Time= 3h, T= 20 °C , Glovebox, Sealed tube, Inert atmosphere, Oppenauer Oxidation Ogiwara, Yohei; Ono, Yuji; Sakai, Norio; Synthesis (Germany); vol. 48; nb. 23; (2016); p. 4143 - 4148; Art.No: SS-2016F0462-OP View in Reaxys

19 %

With cobaltocene, C18H11Cl3FeN4 (1-), sodium hydroxide in toluene, Time= 4h, T= 75 °C , Inert atmosphere, Schlenk technique, Reagent/catalyst Sinha, Suman; Das, Siuli; Sikari, Rina; Parua, Seuli; Brandaõ, Paula; Demeshko, Serhiy; Meyer, Franc; Paul, Nanda D.; Inorganic Chemistry; vol. 56; nb. 22; (2017); p. 14084 - 14100 View in Reaxys

2.3. Typical procedure for oxidation of alcohols General procedure: The copper salt and the ligand (each 0.025 mmol) were added to CH3CN (1 mL) in an Ar atmosphere and stirred for 30min. Then 4-OH-TEMPO (0.025 mmol) and substrate (0.5mmol) were added successively, and the mixture was stirred at room temperature. The reaction progress was checked using thin-layer chromatography. The reaction conversion and yield were obtained from GC measurements using nitrobenzene or nonane as an internal standard, or by column chromatography. With copper(l) iodide, TEMPOL, N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamine in acetonitrile, Time= 24h, T= 20 °C , Inert atmosphere Zhang, Shufang; Miao, Chengxia; Xu, Daqian; Sun, Wei; Xia, Chungu; Chinese Journal of Catalysis; vol. 35; nb. 11; (2014); p. 1864 - 1873 View in Reaxys With 1,4-dioxane, selenium(IV) oxide, T= 80 °C Jerchel; Heck; Justus Liebigs Annalen der Chemie; vol. 613; (1958); p. 171,179 View in Reaxys Furukawa; Kuroiwa; Pharmaceutical Bulletin; vol. 3; (1955); p. 232 View in Reaxys With pyridine, selenium(IV) oxide, T= 90 °C Jerchel; Heck; Justus Liebigs Annalen der Chemie; vol. 613; (1958); p. 171,179 View in Reaxys Furukawa; Kuroiwa; Pharmaceutical Bulletin; vol. 3; (1955); p. 232 View in Reaxys With selenium(IV) oxide, T= 160 °C Jerchel; Heck; Justus Liebigs Annalen der Chemie; vol. 613; (1958); p. 171,179 View in Reaxys Furukawa; Kuroiwa; Pharmaceutical Bulletin; vol. 3; (1955); p. 232 View in Reaxys With manganese(IV) oxide, diethyl ether Sugasawa; Mizukami; Pharmaceutical Bulletin; vol. 3; (1955); p. 393 View in Reaxys With dipotassium peroxodisulfate, water, T= 85 °C

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Horii et al.; Yakugaku Zasshi; vol. 76; (1956); p. 1101; ; (1957); p. 3553 View in Reaxys With lead(IV) acetate, benzene Micovic; Mihailovic; Recueil des Travaux Chimiques des Pays-Bas; vol. 71; (1952); p. 970,974 View in Reaxys 98 % Spectr.

With cyclic iodinane oxide in dichloromethane, Time= 1.5h, Ambient temperature Stickley, Sharon H.; Martin, J. C.; Tetrahedron Letters; vol. 36; nb. 50; (1995); p. 9117 - 9120 View in Reaxys

50 % Chromat.

With oxygen, Mg6Al2Ru0.5(OH)16CO3 in toluene, Time= 24h, T= 60 °C Kaneda, Kiyotomi; Yamashita, Toyokazu; Matsushita, Tsuyoshi; Ebitani, Kohki; Journal of Organic Chemistry; vol. 63; nb. 6; (1998); p. 1750 - 1751 View in Reaxys

91 % Chromat.

With oxygen, Ru-Co-Al-CO3 HT in toluene, Time= 7h, T= 60 °C Matsushita, Tsuyoshi; Ebitani, Kohki; Kaneda, Kiyotomi; Chemical Communications; nb. 3; (1999); p. 265 - 266 View in Reaxys

77 % Chromat.

With N-chloro-succinimide, dodecyl methyl sulfide, triethylamine in tetrahydrofuran, Time= 2.5h, T= -40 °C , Corey-Kim oxidation Ohsugi, Shin-Ichi; Nishide, Kiyoharu; Oono, Keiji; Okuyama, Kazunori; Fudesaka, Masato; Kodama, Sumiaki; Node, Manabu; Tetrahedron; vol. 59; nb. 42; (2003); p. 8393 - 8398 View in Reaxys With C30H26N3OP, potassium carbonate, copper(l) chloride, 1-methyl-pyrrolidin-2-one, Time= 14h, T= 110 °C Tsai, Weiwen; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung; Journal of Organometallic Chemistry; vol. 690; nb. 2; (2005); p. 415 - 421 View in Reaxys

44 % Chromat.

With sodium periodate, sulfuric acid in water, Time= 8h, T= 95 °C Shaikh, Tanveer Mahammad Ali; Emmanuvel, Lourdusamy; Sudalai, Arumugam; Journal of Organic Chemistry; vol. 71; nb. 13; (2006); p. 5043 - 5046 View in Reaxys With 2,2,6,6-tetramethyl-piperidine-N-oxyl, oxygen, sodium nitrite, iron(III) chloride in dichloromethane, acetonitrile, Time= 6h, p= 1500.12Torr , Heating Wang, Naiwei; Liu, Renhua; Chen, Jiping; Liang, Xinmiao; Chemical Communications; nb. 42; (2005); p. 5322 - 5324 View in Reaxys

100 % Turnov.

With dihydrogen peroxide, SiW9Al3, Time= 5h, T= 90 °C Wang, Jianmin; Yan, Liang; Qian, Guang; Li, Shunqing; Yang, Keli; Liu, Haitao; Wang, Xiaolai; Tetrahedron; vol. 63; nb. 8; (2007); p. 1826 - 1832 View in Reaxys

99 % Chromat.

With Ru3+-exchanged hydroxyapatite (RuHAP), oxygen in toluene, Time= 10h, T= 80 °C , p= 760.051Torr , Oxidation Yamaguchi, Kazuya; Mori, Kohsuke; Mizugaki, Tomoo; Ebitani, Kohki; Kaneda, Kiyotomi; Journal of the American Chemical Society; vol. 122; nb. 29; (2000); p. 7144 - 7145 View in Reaxys

98 % Chromat.

With potassium tert-butylate, p-benzoquinone, [Ir(trop2datch)]OTf in chlorobenzene, Time= 3h, T= 25 °C Koenigsmann, Martin; Donati, Nicola; Stein, Daniel; Schoenberg, Hartmut; Harmer, Jeffrey; Sreekanth, Anandaram; Gruetzmacher, Hansjoerg; Angewandte Chemie - International Edition; vol. 46; nb. 19; (2007); p. 3567 - 3570 View in Reaxys

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17 % Chromat.

With oxygen, isobutyraldehyde, ruthenium(III) meso-tetraphenylporphyrin chloride in various solvent(s), Time= 1h, T= 60 °C , p= 760.051Torr Ji, Hong-Bing; Yuan, Qiu-Lan; Zhou, Xian-Tai; Pei, Li-Xia; Wang, Le-Fu; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 22; (2007); p. 6364 - 6368 View in Reaxys With air, gold supported on ceria nanoparticles in toluene, Time= 7h, T= 90 °C Abad, Alberto; Corma, Avelino; Garcia, Hermenegildo; Chemistry - A European Journal; vol. 14; nb. 1; (2008); p. 212 - 222 View in Reaxys

99 % Chromat.

With oxygen, Ru/copper hydrogen phosphate in toluene, Time= 18h, T= 80 °C , Product distribution Liu, Junhua; Wang, Fang; Sun, Kunpeng; Xu, Xianlun; Advanced Synthesis and Catalysis; vol. 349; nb. 16; (2007); p. 2439 - 2444 View in Reaxys With oxygen, Au/Ca3Al3O9 in toluene, Time= 4h, T= 80 °C Su, Fang-Zheng; Liu, Yong-Mei; Wang, Lu-Cun; Cao, Yong; He, He-Yong; Fan, Kang-Nian; Angewandte Chemie - International Edition; vol. 47; nb. 2; (2008); p. 334 - 337 View in Reaxys With Ag/hydrotalcite in para-xylene, Time= 30h, T= 130 °C Mitsudome, Takato; Mikami, Yusuke; Funai, Hisashi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Angewandte Chemie - International Edition; vol. 47; nb. 1; (2008); p. 138 - 141 View in Reaxys

96 %Chromat.

With 2,2'-azobis(isobutyronitrile), oxygen in acetonitrile, Time= 11h, T= 100 °C , p= 2584.17Torr , Autoclave Bordoloi, Ankur; Sahoo, Suman; Lefebvre; Halligudi; Journal of Catalysis; vol. 259; nb. 2; (2008); p. 232 - 239 View in Reaxys

> 99 %Chromat.

With Au/hydrotalcite in para-xylene, Time= 48h, T= 120 °C , Inert atmosphere Fang, Wenhao; Zhang, Qinghong; Chen, Jing; Deng, Weiping; Wang, Ye; Chemical Communications; vol. 46; nb. 9; (2010); p. 1547 - 1549 View in Reaxys

16 %Chromat.

With acetaldehyde, Time= 24h, T= 30 °C , pH= 7.5, aq. phosphate buffer, Microbiological reaction, Combinatorial reaction / High throughput screening (HTS), Oppenauer oxidation, chemoselective reaction Orbegozo, Thomas; De Vries, Johannes G.; Kroutil, Wolfgang; European Journal of Organic Chemistry; nb. 18; (2010); p. 3445 - 3448 View in Reaxys

76 %Chromat.

With oxygen in toluene, Time= 18h, T= 100 °C Nagashima, Kohji; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi; Green Chemistry; vol. 12; nb. 12; (2010); p. 2142 - 2144 View in Reaxys With Ru/Al2O3, oxygen in toluene, Time= 7h, T= 90 °C , p= 3750.38Torr , chemoselective reaction Zotova, Natalia; Hellgardt, Klaus; Kelsall, Geoffrey H.; Jessiman, Alan S.; Hii, King Kuok Mimi; Green Chemistry; vol. 12; nb. 12; (2010); p. 2157 - 2163 View in Reaxys

71 %Chromat.

With water, oxygen, sodium nitrite, Time= 24h, T= 30 °C , p= 1500.15Torr , Ionic liquid, Autoclave Miao, Cheng-Xia; Wang, Jin-Quan; Yu, Bing; Cheng, Wei-Guo; Sun, Jian; Chanfreau, Sebastien; He, Liang-Nian; Zhang, Suo-Jiang; Chemical Communications; vol. 47; nb. 9; (2011); p. 2697 - 2699 View in Reaxys

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With 2,2'-azinobis(3-ethylbenzthiazolinesulfonate), copper(ll) sulfate pentahydrate, oxygen, horseradish peroxidase, Time= 20h, T= 20 °C , p= 3000.3Torr , pH= 7, Microbiological reaction, aq. phosphate buffer, Enzymatic reaction Fuchs, Michael; Schober, Markus; Pfeffer, Jan; Kroutil, Wolfgang; Birner-Gruenberger, Ruth; Faber, Kurt; Advanced Synthesis and Catalysis; vol. 353; nb. 13; (2011); p. 2354 - 2358 View in Reaxys 71 %Chromat.

Typical procedure for the oxidation of primary benzylic alcohols (Table 4). General procedure: To a mixture of alcohol 4 (1 mmol), tridecane (50 μL, 0.205 mmol, internal standard) and DME (1 mL) in a screw cap tube was added t-BuONO (198 μL, 1.5 mmol, 1.5 equiv.) under N2 atmosphere. The solution was stirred under the conditions indicated in table 4. The reaction mixture was analyzed by GC and the product was isolated by column chromatography (SiO2) for the characterization. With tert.-butylnitrite in 1,2-dimethoxyethane, Time= 17h, T= 100 °C , Inert atmosphere Hamasaki, Akiyuki; Kuwada, Hideyuki; Tokunaga, Makoto; Tetrahedron Letters; vol. 53; nb. 7; (2012); p. 811 - 814 View in Reaxys With oxygen in toluene, Time= 4h, T= 100 °C , p= 760.051Torr Chen, Gongzhou; Wu, Shijian; Liu, Hongli; Jiang, Huanfeng; Li, Yingwei; Green Chemistry; vol. 15; nb. 1; (2013); p. 230 235 View in Reaxys

92.8 %Chromat.

With iron(III) chloride hexahydrate, oxygen, sodium nitrite in toluene, Time= 6h, T= 60 °C , p= 760.051Torr , Catalytic behavior Wang, Lianyue; Li, Jun; Zhao, Xiaoping; Lv, Ying; Zhang, Hengyun; Gao, Shuang; Tetrahedron; vol. 69; nb. 30; (2013); p. 6041 - 6045 View in Reaxys

74 %Chromat.

Typical procedure for the oxidation process: General procedure: In a three-neck round bottom flask, KCC-1/TEMPO (0.05 g, about 0.02 mmol) was dispersed in acetonitrile (15 mL) and sonicated for 15 min followed by the addition of alcohol (2 mmol), NaNO2 (6.9 mg, 0.1 mmol). Oxygen was introduced to the flask with a rate of 0.004 m3/h and the flask was placed in an oil bath thermostated at 80 °C. The reaction was initiated by the addition of 10percent H2SO4 solution (0.1 mL). When the reaction was finished, the catalyst was recovered by filtration and used after drying without further treatment. After extraction with CH2Cl2 and drying over MgSO4, the crude product was analyzed by GC. With sulfuric acid, oxygen, sodium nitrite in acetonitrile, Time= 5h, T= 80 °C Zhu, Jie; Zhao, Xue-Jing; Wang, Peng-Cheng; Lu, Ming; Chemistry Letters; vol. 42; nb. 12; (2013); p. 1505 - 1507 View in Reaxys

98 %Chromat.

With palladium in UiO-67, air in toluene, Time= 20h, T= 120 °C , Green chemistry Chen, Liyu; Chen, Huirong; Luque, Rafael; Li, Yingwei; Chemical Science; vol. 5; nb. 10; (2014); p. 3708 - 3714 View in Reaxys Catalytic test: aerobic oxidation of benzyl alcohol General procedure: The reaction was carried out in a batch-type reaction withstirring. Typically, the catalyst powder (50 mg), benzyl alcohol(2 mmol) and solvent (10 mL) were placed in a 50 mL round-bottomflask; a LED lamp (200 W, 400–800 nm) was used as a light source.The system was filled with pure oxygen and sealed. A small amountof reactant was separated at regular intervals and quantitativelyanalyzed by GC. Afterward, the products were identified with aGC–MS spectrometer. For comparison, the reaction was performedsimultaneously in the dark under the same conditions With oxygen in 1,4-dioxane, Time= 46h, T= 39.84 °C , p= 760.051Torr , Irradiation Yu, Jing; Li, Jingyi; Wei, Huili; Zheng, Jianwei; Su, Haiquan; Wang, Xiaojing; Journal of Molecular Catalysis A: Chemical; vol. 395; (2014); p. 128 - 136 View in Reaxys With O40PW12 (3-)*3C40H48Cl4N4P2Ru(1+), water, oxygen, Time= 3h, T= 100 °C , p= 7500.75Torr , Ionic liquid

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Wang, Sa-Sa; Zhang, Jing; Zhou, Cheng-Liang; Vo-Thanh, Giang; Liu, Ye; Catalysis Communications; vol. 28; (2012); p. 152 - 154 View in Reaxys With Iron(III) nitrate nonahydrate, 2C27H56N2O2 (1+)*2Br(1-)*CH4N2O, oxygen in neat (no solvent), Time= 9h, T= 60 °C , Green chemistry Zhang, Yuecheng; Lü, Fenglian; Cao, Xiaohui; Zhao, Jiquan; RSC Advances; vol. 4; nb. 76; (2014); p. 40161 - 40169 View in Reaxys With silver(0) nanoparticles supported on silica-coated ferrite in toluene, Time= 24h, Inert atmosphere, Reflux Bayat, Ahmad; Shakourian-Fard, Mehdi; Ehyaei, Nona; Mahmoodi Hashemi, Mohammad; RSC Advances; vol. 5; nb. 29; (2015); p. 22503 - 22509 View in Reaxys 83 %Chromat.

With chitosan/polyacrylamide entrapped silver nanoparticles in para-xylene, Time= 12h, T= 130 °C , Inert atmosphere Kurhe, Deepak K.; Fernandes, Thomson A.; Deore, Tushar S.; Jayaram, Radha V.; RSC Advances; vol. 5; nb. 58; (2015); p. 46443 - 46447 View in Reaxys 2.4. Typical catalytic procedure for selective aerobic oxidation of benzyl alcohol General procedure: The catalytic reaction was carried out under the follow-ing conditions: heterogeneous copper (II) catalyst (4 molpercent), base(0.50 mmol), TEMPO (0.25 mmol), benzyl alcohol (0.50 mmol) andCH3CN (2.5 mL). The air in the above reaction system was evacuatedand an oxygen balloon was supplied. The solution was centrifugedafter stirring for 24 h and the filtered liquid samples were analyzedvia gas chromatography–mass spectrometry (Agilent 7890/5975C-GC/MSD) using nitrobenzene as the internal standard. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium hydrogencarbonate in acetonitrile, Time= 24h, T= 60 °C , p= 760.051Torr Hou, Junying; Luan, Yi; Tang, Jia; Wensley, Allison M.; Yang, Mu; Lu, Yunfeng; Journal of Molecular Catalysis A: Chemical; vol. 407; (2015); p. 53 - 59 View in Reaxys With potassium nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 14h, T= 75 °C , p= 760.051Torr , Green chemistry Jin, Zhaokui; Luan, Yi; Yang, Mu; Tang, Jia; Wang, Jingjing; Gao, Hongyi; Lu, Yunfeng; Wang, Ge; RSC Advances; vol. 5; nb. 96; (2015); p. 78962 - 78970 View in Reaxys Typical procedure for the oxidation of primary alcohols. General procedure: A 5-mL two-necked, round-bottom flask equipped with a magnetic stirrer and an oxygen balloon was charged in succession with 0.0106 g(0.05 mmol) of Cu(OTf), 0.0078 g (0.05 mmol) of TEMPO, 0.0136 g (0.04 mmol) of benzoxazine ligand L, and 1 mL of methylene chloride. The corresponding alcohol, 1 mmol, was then added at 25°C under stirring, and oxygen from the balloon was introduced through a three-way valve. The progress of the reaction was monitored by GLC using a suitable column. With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 6,8-di(tert-butyl)-3-[2-(1H-imidazol-4-yl)ethyl]-3,4-dihydro-2H-1,3benzoxazine, oxygen, copper(I) triflate in dichloromethane, Time= 4h, T= 25 °C Zhang; Huang; Lü; Cao; Zhao; Russian Journal of General Chemistry; vol. 85; nb. 8; (2015); p. 1965 - 1972; Zh. Obshch. Khim. View in Reaxys 2.4 Catalytic oxidation of alcohols General procedure: In a typical process, into a 5ml two-necked, round-bottom flask equipped with a magnetic stirrer and a thermometer were added the ruthenium complex [Ru(pymieb)(pydic)] (0.002mmol) and the substrate alcohol (2mmol) successively. The mixture was heated to 40°C under stirring. Then t-butyl hydroperoxide (TBHP) was added dropwise to the mixture and the temperature was kept at 40°C until completion of the reaction. The reaction samples were analyzed on a Shandong Lunan Ruihong Gas Chromatograph (SP-6800A) equipped with a FID detector and a SE 30 column (30m×0.5mm). The conditions used in gas chromatography were temperature of the detector 280°C, column temperature 130–220°C (varying with alcohols), pressure of the carrier gas 0.05–0.07MPa (varying with alcohols).

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With tert.-butylhydroperoxide, Ru[2-(2-pyridymethylimino)ethylbenzimidazole]pyridinedicarboxylate in neat (no solvent), Time= 2h, T= 40 °C Zhang, Yuecheng; Liu, Liu; Cao, Xiaohui; Zhao, Jiquan; Polyhedron; vol. 105; (2016); p. 170 - 177 View in Reaxys With dihydrogen peroxide in water, Time= 60h, T= 110 °C , Schlenk technique, Green chemistry Yao, Xianfang; Bai, Cuihua; Chen, Junying; Li, Yingwei; RSC Advances; vol. 6; nb. 32; (2016); p. 26921 - 26928 View in Reaxys 91 %Chromat.

With tert.-butylhydroperoxide in dimethyl sulfoxide, Time= 4h, T= 110 °C Zhou, Qiangfei; Wan, Zijuan; Yuan, Xiaofeng; Luo, Jun; Applied Organometallic Chemistry; vol. 30; nb. 4; (2016); p. 215 220 View in Reaxys Catalytic oxidation. General procedure: Oxidation reaction was carried out in a 10 mL three-necked round bottom flask equipped with a mechanical stirrer and a condenser connected to a balloon filled with oxygen. Typically, to alcohol (2 mmol) dissolved in 3 mL of acetonitrile were added CuBr2 (0.1 mmol), TEMPO (0.08 mmol), and 0.11 g of the pyridinecarboxaldimine grafted to magnetic nanoparticles. The system was purged with oxygen and sealed. Stirring it for 0.5 h was followed by addition of the base (0.3 mmol). The process was monitored by GC. Upon completion of the reaction, the supported pyridinecarboxaldimine was collected by a magnet and washed with acetonitrile repeatedly. The following drying under vacuum to constant weight made the nanoparticles ready for another run. With 1-methyl-1H-imidazole, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, copper(ll) bromide in acetonitrile, Time= 8h, T= 50 °C Zhang; Sun; Guo; Su; Zhao; Russian Journal of General Chemistry; vol. 86; nb. 4; (2016); p. 944 - 952; Zh. Obshch. Khim.; vol. 86; nb. 4; (2016); p. 944 - 952,9 View in Reaxys

60 %Chromat.

With C39H29N5ORu(2+)*2ClO4 (1-), dihydrogen peroxide in water, acetonitrile, Time= 12h, T= 70 °C , Reflux Singha Hazari, Arijit; Ray, Ritwika; Hoque, Md Asmaul; Lahiri, Goutam Kumar; Inorganic Chemistry; vol. 55; nb. 16; (2016); p. 8160 - 8173 View in Reaxys With oxygen in toluene, Time= 2h, T= 80 °C , Reagent/catalyst Tan, Yu; Sun, Dalei; Chen, Libao; Li, Cheng Chao; New Journal of Chemistry; vol. 40; nb. 10; (2016); p. 8364 - 8370 View in Reaxys With oxygen in ethanol, Time= 16h, T= 80 °C , p= 760.051Torr , Autoclave, Reagent/catalyst Slot, Thierry K.; Eisenberg, David; van Noordenne, Dylan; Jungbacker, Peter; Rothenberg, Gadi; Chemistry - A European Journal; vol. 22; nb. 35; (2016); p. 12307 - 12311 View in Reaxys 2.4. Evaluation of photocatalytic activity General procedure: 10 mg catalyst was suspended in 1.5 mL benzotrifluoride (BTF)solvent containing alcohol (0.1 mmol). The choice of BTF solventwas because it is inert to oxidation and has superior oxygen solubility[24]. The catalyst was blended evenly in the solution withmagnetic stirring for 30 min before illumination. Reaction temperaturewas kept at 20 °C with a watercooling system. The reactionsolution was illuminated by a 300W Xe lamp with a UV-cutoff filterwhere a majority of the light of wavelength shorter than420 nm was blocked. The reaction solution was analyzed with anAgilent Gas Chromatograph (GC7890) equipped with a flame ionizationdetector and a β-DEX 225 capillary column using dodecaneor undecane as the internal standard. The chemical structures ofproducts were confirmed by GC-mass spectrometry (MS) (AgilentTechnologies, GC6890N-MS5975). Stage 1: With oxygen, Time= 0.5h Stage 2:, Time= 6h, T= 20 °C , p= 750.075Torr , Irradiation Zhang, Bao; Li, Jun; Gao, Yuying; Chong, Ruifeng; Wang, Zhiliang; Guo, Lin; Zhang, Xianwen; Li, Can; Journal of Catalysis; vol. 345; (2017); p. 96 - 103 View in Reaxys

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With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen, sodium hydrogencarbonate in acetonitrile, Time= 12h, T= 60 °C , p= 760.051Torr Hou, Junying; Luan, Yi; Yu, Jie; Qi, Yue; Wang, Ge; Lu, Yunfeng; New Journal of Chemistry; vol. 40; nb. 12; (2016); p. 10127 - 10135 View in Reaxys 52 %Chromat.

With oxygen, Time= 18h, T= 60 °C , Green chemistry Liu, Gui; Liu, Junhua; Li, Wenxiu; Liu, Cheng; Wang, Fang; He, Junkai; Guild, Curtis; Jin, Jing; Kriz, David; Suib, Steven L.; Applied Catalysis A: General; vol. 535; (2017); p. 77 - 84 View in Reaxys 2.2 General procedure for the aerobic oxidation ofalcohols using NHPI/O2/CoTPP-Zn2Al-LDH system In a typical experiment, a solution of NHPI (0.6 mmol,20 molpercent) and CoTPP-Zn2Al-LDH (0.01 mmol of CoTPP content, 30 mg) in PhCN or CH3CN (10 mL) was prepared in a 25mL round-bottom flask equippedwith magnetic stirrer. To this solution alcohol (3 mmol)was added and the resulting mixture was stirred at100 or 80 °C. Then dioxygen was bubbled through thesolution at a rate of 20mLmin−1. All the productswere identified by GC-MS and quantified at differentintervals during the reaction by GC-FID (ShimadzuGC-2010AF). With N -hydroxyphthalimide, oxygen in acetonitrile, Time= 44h, T= 80 °C , Reagent/catalyst Zhou, Weiyou; Chen, Dongwei; Cui, Aijun; Qian, Junfeng; He, Mingyang; Chen, Qun; Journal of Chemical Sciences; vol. 129; nb. 3; (2017); p. 295 - 299 View in Reaxys With potassium nitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 12h, p= 760.051Torr Miao, Zongcheng; Shu, Xin; Ramella, Daniele; RSC Advances; vol. 7; nb. 5; (2017); p. 2773 - 2779 View in Reaxys With nickel dichloride in water, Time= 6h, T= 20 °C , pH= 9, Inert atmosphere, Irradiation Zhao, Lei-Min; Meng, Qing-Yuan; Fan, Xiang-Bing; Ye, Chen; Li, Xu-Bing; Chen, Bin; Ramamurthy, Vaidhyanathan; Tung, Chen-Ho; Wu, Li-Zhu; Angewandte Chemie - International Edition; vol. 56; nb. 11; (2017); p. 3020 - 3024; Angew. Chem.; vol. 129; nb. 11; (2017); p. 3066 - 3070,5 View in Reaxys 2.3. Typical experimental procedure for photocatalytic test General procedure: In a general procedure for the photocatalytic test, a suspensionof 8 mg catalyst0.1 mmol aryl alcohol and 10 mL dodecane in1.5 mL of reagent grade benzotrifluoride (BTF) was transferred intoa 20 mL quartz bottle and magnetically stirred at 1000 rpm duringthe reaction. A stream of pure O2 at 1 atm pressure was bubbledinto the reaction system. The suspension was irradiated by a300-W Xenon Illuminator System with a UV cut-off filter in anair-conditioned room to maintain the reaction temperature at30 C. The photocatalytic reactions of fresh benzyl alcohol-BTFdodecanemixture under the same reaction conditions wererepeated 5 times to confirm the reliability of the data. After thereaction, reaction solutions (60 mL) were filtered by a one-timeplastic filter and added into 0.5 mL ethanol for gas chromatographanalysis (Agilent 7890A equipped with an FID detector). The specificGC parameters were as follows: HP-5 capillary column(30 m 0.32 mm 0.25 lm); detector temperature (300 C); splitratio (20:1); injector temperature (300 C). The oven temperaturewas maintained at 50 C for 5 min, and then raised to 120 C at arate of 10 C min1, finally the temperature increased to 300 C.Continuous nitrogen gas (20 mL min1) was used as a carrier gas.Here, dodecane was used as an internal standard to calculate theconversion of alcohol and selectivity for aldehyde. The carbon balancewas evaluated to be >99percent for all substrates. Thus, there is negligibleformation of volatile products, such as CO and CO2. Theproducts quantification were confirmed by comparison with theretention time of commercial samples and further confirmed bygas chromatography mass spectrometry (GC–MS) (430 GC Varian,USA). Controlled photoactivity experiments using a series of radicalscavengers, ammonium oxalate (AO) as the scavenger for photogeneratedholes, tertbutyl alcohol (TBA) as the scavenger forhydroxyl radicals, K2S2O8 as the scavenger for electrons, and benzoquinone(BQ) as scavenger for superoxide radical species wereperformed in a similar manner to the above photocatalytic experimentwith radical scavengers (0.1 mmol) added to the reactionsystem. With β,β,β-trifluorotoluene, oxygen in dodecane, Time= 2.5h, T= 30 °C , p= 760.051Torr , Irradiation Yang, Xue; Zhao, Hui; Feng, Jifei; Chen, Yanning; Gao, Shuiying; Cao, Rong; Journal of Catalysis; vol. 351; (2017); p. 59 66 View in Reaxys

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93 %Chromat.

2.2. General procedure for the aerobic oxidation of various substrates General procedure: To a dried 45 mL tube equipped with a magnetic stirring, 2 mL acetonitrile, 0.5 mmol substrate and 0.046 mmol NO2 were sequentially added (note: the air in the tube was not removed). Then the reaction tube was sealed and stirred magnetically at a constant-temperature to perform the reaction for 5 h. Once the reaction time was reached, GCanalysis of the mixture provided the GC yields of the products. Then the crude product from another parallel experiment was purified by silicagel chromatography to give the desired product. With Nitrogen dioxide in acetonitrile, Time= 5h, T= 140 °C , p= 760.051Torr , Sealed tube Ren, Fangping; Tian, Xinzhe; Ren, Yun-Lai; Zhao, Shuang; Wang, Jianji; Zhao, Bo; Catalysis Communications; vol. 101; (2017); p. 98 - 101 View in Reaxys With dihydrogen peroxide in water, Time= 7h, T= 90 °C , Reagent/catalyst Wang, Hefang; Wang, Cunyue; Yang, Yongfang; Zhao, Meng; Wang, Yanji; Catalysis Science and Technology; vol. 7; nb. 2; (2017); p. 405 - 417 View in Reaxys With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in acetonitrile, Time= 1.5h, p= 750.075Torr , Irradiation Zhang, Yichi; Wang, Zhan; Lang, Xianjun; Catalysis Science and Technology; vol. 7; nb. 21; (2017); p. 4955 - 4963 View in Reaxys 1 :The 2 - pyridine methanol ice water cooling to join the PCC, the 2 - pyridine methanol with PCC in a molar ratio of 1: 2.5, temperature is 1 °C; then the reaction at room temperature, a temperature of 25 degree Celcius, through thin layer chromatographic monitoring to the reaction is complete. With pyridinium chlorochromate, T= 1 - 25 °C , Temperature, Concentration, Reagent/catalyst Patent; Liu Ruihai; (6 pag.); CN107286080; (2017); (A) Chinese View in Reaxys With silver nanoparticles immobilized onto poly(4-vinylpyridine)-functionalized Fe3O4 nanoparticles in toluene, Time= 24h, Inert atmosphere, Reflux Bayat, Ahmad; Shakourian-Fard, Mehdi; Talebloo, Nazanin; Hashemi, Mohammed Mahmoodi; Applied Organometallic Chemistry; vol. 32; nb. 2; (2018); Art.No: E4061 View in Reaxys

N N H

Rx-ID: 45521127 View in Reaxys 2/115 Yield 89 %

Conditions & References IBX oxidation of amines A solution of amine (55 mg, 0.45 mmol) and IBX (252 mg, 0.90 mmol) in 10 mL of CHCl3 was heated at reflux with vigorous stirring for 24 h. The resulting suspension was filtered and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel and ethyl acetate) to afford the desired product (41 mg, 89percent yield). 1H NMR (400 MHz, 25 °C, CDCl3): β = 10.08 (s, 1H), 7.93 (d, 2H, J = 8.0 Hz), 7.68 (d, 1H, J = 4.0 Hz), 7.59 (t, 2H, J = 4.0 Hz) ppm. 13C NMR (100 MHz, 25 °C, CDCl3): β = 193.44, 152.75, 150.21, 137.10, 127.90, 121.72 ppm. ESI–MS: M + Na+, found 130.1 (calc. 130.11). With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in chloroform, Time= 24h, Reflux Chen, Li-Xia; Huang, Yin-Hui; Cong, Hang; Tao, Zhu; Chemical Papers; vol. 72; nb. 3; (2018); p. 661 - 667 View in Reaxys

85 %

2 : Example 2:A method for the direct synthesis of an aldehyde by an amine comprising the steps of: Respectively, weighed o-iodobenzoic acid 230 mg,2 - [(methylamino) methyl] pyridine 55 mg To 10 ml of chloroform,The reaction was stirred under reflux for 24 hours.Spontaneously cooled to room temperature and then filtered to remove IBX and its reduction products o-iodo benzoic acid (IBA),The filtrate was washed with 10percent Na0H solution,1M hydrochloric acid, wa-

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ter and saturated sodium chloride solution were washed 3 times,Each time about 10ml, solvent chloroform by rotary evaporation removed,Product directly with nuclear magnetic characterization,The yield of 2-pyridine formaldehyde was 85percent. With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in chloroform, Time= 24h, Reflux Patent; Guizhou University; CONG, Hang; WANG, Fang; TAO, Zhu; (8 pag.); CN105732351; (2016); (A) Chinese View in Reaxys O N

N O

Rx-ID: 47227206 View in Reaxys 3/115 Yield 88 %

Conditions & References With ammonium formate, silica gel, zinc in methanol, Time= 0.166667h, T= 20 °C , chemoselective reaction Rajesh; Journal of Heterocyclic Chemistry; vol. 55; nb. 2; (2018); p. 486 - 491 View in Reaxys

N O

Rx-ID: 26650 View in Reaxys 4/115 Yield 50.2 %

Conditions & References With water, oxygen, CrV0.95P0.05O4, T= 299.84 °C Song, Zhaoxia; Matsushita, Toshiyuki; Shishido, Tetsuya; Takehira, Katsuomi; Chemical Communications; nb. 12; (2002); p. 1306 - 1307 View in Reaxys With oxygen, V-Mo oxide, Mechanism Leitis, L. Ya.; Skolmeistere, R. A.; Shimanskaya, M. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 23; nb. 1; (1987); p. 52 - 55; Khimiya Geterotsiklicheskikh Soedinenii; vol. 23; nb. 1; (1987); p. 64 - 67 View in Reaxys With water, vanadia, molybdenum(VI) oxide, T= 410 °C , auf Silicagel Mathes et al.; Chemische Berichte; vol. 84; (1951); p. 452,456 View in Reaxys Patent; Raschig G.m.b.H.; US2749351; (1953) View in Reaxys Patent; Raschig G.m.b.H.; DE936871; (1951) View in Reaxys With selenium(IV) oxide Mlochowski, Jacek; Kubicz, Elzbieta; Kloc, Krystian; Mordarski, Marian; Peczynska, Wanda; Syper, Ludwik; Liebigs Annalen der Chemie; (1988); p. 455 - 464 View in Reaxys With benzeneseleninic anhydride in chlorobenzene, Time= 3h, T= 130 °C Barton, Derek H. R.; Hui, Raymond A. H. F.; Ley, Steven V.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 9; (1982); p. 2179 - 2186 View in Reaxys Reaction Steps: 3 1: steam; air; catalyst from V2O5/MoO3 upon silica gel / 380 °C 2: palladium/ asbestos; ethanolic HCl / Hydrogenation 3: lead (IV)-acetate; benzene

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With lead(IV) acetate, hydrogenchloride, air, magnesium hydrosilicate, MoO3 upon silica gel, catalyst from V2O5, steam, palladium, benzene Mathes et al.; Chemische Berichte; vol. 84; (1951); p. 452,456 View in Reaxys 22 %Chromat.

Isolation of the oxygenated product: General procedure: In a test tube, substrate (1.0 mmol) and CuCl2•2H2O(0.10 mmol) were dissolved in DMSO (3.0 mL). O2 balloon (1 atm) was attached at top of the test tube, and inner atmosphere was replaced by O2. After stirring at 100 °C for 45 hours,reaction mixture was diluted by CH2Cl2 (20 mL) and washed with sat. Na2CO3 aq (10 mL).The separated water phase was then extracted with CH2Cl2 (10 mL×2). The combined organicphase was washed with brine (20 mL) and dried over Na2SO4. After removal of Na2SO4 byfiltration, evaporation of the solvent gave brown oil, from which the desired product wasisolated by silica column chromatography (eluent: EtOAc / n-Hexane = 1 / 10 to 1 / 1). With copper(II) choride dihydrate, oxygen in dimethyl sulfoxide, Time= 45h, T= 100 °C , p= 760.051Torr Abe, Tsukasa; Tanaka, Shinji; Ogawa, Atsuko; Tamura, Masanori; Sato, Kazuhiko; Itoh, Shinobu; Chemistry Letters; vol. 46; nb. 3; (2017); p. 348 - 350 View in Reaxys Reaction Steps: 4 1: acetic acid; dihydrogen peroxide / 16 h / 65 °C 2: 5 h / 90 °C 3: potassium hydoxide / 5 h 4: pyridinium chlorochromate / 1 - 25 °C With dihydrogen peroxide, acetic acid, pyridinium chlorochromate, potassium hydoxide Patent; Liu Ruihai; (6 pag.); CN107286080; (2017); (A) Chinese View in Reaxys

N O

N N OH

Rx-ID: 264922 View in Reaxys 5/115 Yield

Conditions & References With lead(IV) acetate, benzene Mathes et al.; Chemische Berichte; vol. 84; (1951); p. 452,456 View in Reaxys

99 %Chromat.

With Na0274MnO2*6H2O, oxygen in butan-1-ol, Time= 1h, T= 100 °C , p= 760.051Torr , Green chemistry Escande, Vincent; Lam, Chun Ho; Coish, Philip; Anastas, Paul T.; Angewandte Chemie - International Edition; vol. 56; nb. 32; (2017); p. 9561 - 9565; Angew. Chem.; vol. 129; nb. 32; (2017); p. 9689 - 9693,5 View in Reaxys

N OH

Rx-ID: 1573617 View in Reaxys 6/115 Yield 90 %

Conditions & References With (CH3)2NCH2NpSiH2Ph, T= 110 - 140 °C Corriu, R. J. P.; Lanneau, G. F.; Perrot, M.; Tetrahedron Letters; vol. 28; nb. 34; (1987); p. 3941 - 3944 View in Reaxys With D-glucose, sodium citrate, magnesium chloride in aq. phosphate buffer, Time= 3h, T= 28 °C , pH= 7.4, Enzymatic reaction

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Schwendenwein, Daniel; Fiume, Giuseppe; Weber, Hansjörg; Rudroff, Florian; Winkler, Margit; Advanced Synthesis and Catalysis; vol. 358; nb. 21; (2016); p. 3414 - 3421 View in Reaxys With carboxylic acid reductase, Green chemistry, Enzymatic reaction, Kinetics Finnigan, William; Thomas, Adam; Cromar, Holly; Gough, Ben; Snajdrova, Radka; Adams, Joseph P.; Littlechild, Jennifer A.; Harmer, Nicholas J.; ChemCatChem; vol. 9; nb. 6; (2017); p. 1005 - 1017 View in Reaxys

N O

Rx-ID: 5406794 View in Reaxys 7/115 Yield

Conditions & References

96 %

Patent; LOS ALAMOS NATIONAL SECURITY, LLC; US2012/232279; (2012); (A1) English View in Reaxys

89.1%

4 : pyridine-2-aldehyde EXAMPLE 4 pyridine-2-aldehyde 158 g of 2-vinylpyridine are dissolved in 1 liter of methanol and reacted with ozone, and subsequently hydrogenated, analogously to the procedure indicated in Example 1. 28.9 standard liters of hydrogen, corresponding to 86percent of theory, are absorbed during the hydrogenation. Working up is carried out as in Example 1, and the residue containing the reaction product is purified by rectification. 143 g of pyridine-2-aldehyde boiling at 59°-62° C. 10, corresponding to a yield of 89.1percent of theory, are obtained thereby. Patent; Chemie Linz Gesellschaft m.b.H.; US4769464; (1988); (A) English View in Reaxys

84 %

14 Patent; DSM FINE CHEMICALS AUSTRIA NFG GmbH and Co KG; WO2008/77769; (2008); (A1) English View in Reaxys Meyers,A.I. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 36 - 56 View in Reaxys Callighan; Wilt; Journal of Organic Chemistry; vol. 26; (1961); p. 4912,4913 View in Reaxys Patent; Nepera Chemical Co.; Inc.; US3274206; (1964); ; vol. 65; nb. 16947c; (1966) View in Reaxys Iversen; Acta Chemica Scandinavica (1947-1973); vol. 24; (1970); p. 2459,2461 View in Reaxys Papadopoulos et al.; Journal of Organic Chemistry; vol. 31; (1966); p. 615 View in Reaxys Krueger; Krueger; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 10; (1970); p. 184,185 View in Reaxys Rutner; Spoerrl; Journal of Organic Chemistry; vol. 28; (1963); p. 1898,1899 View in Reaxys Patent; Shulton, Inc.; US3435064; (1965); ; vol. 70; nb. 96483d; (1969) View in Reaxys Mamaev; Gracheva; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 7; (1971); p. 783; Khimiya Geterotsiklicheskikh Soedinenii; vol. 7; (1971); p. 838 View in Reaxys Biniecki; Gutkowska; Acta poloniae pharmaceutica; vol. 23; nb. 3; (1966); p. 201 - 206 View in Reaxys Katritzky et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1979); p. 2493,2495 View in Reaxys Backeberg; Staskun; Journal of the Chemical Society; (1962); p. 3961 View in Reaxys Fetizon et al.; Journal of Heterocyclic Chemistry; vol. 13; (1976); p. 525

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View in Reaxys Abramovitch et al.; Journal of the Chemical Society, Chemical Communications; (1974); p. 693 View in Reaxys Meyers; Nabeya; Chemical Communications (London); (1967); p. 1163 View in Reaxys Schipper; Cinnamon; Rascher; Chiang; Oroshnik; Tetrahedron Letters; vol. 9; nb. 59; (1968); p. 6201 - 6204 View in Reaxys Lejtis; Simanskaja; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 5; (1969); p. 212; Khimiya Geterotsiklicheskikh Soedinenii; vol. 5; (1969); p. 281 View in Reaxys Newkome et al.; Journal of the Chemical Society, Chemical Communications; (1974); p. 410 View in Reaxys Cacchi et al.; Synthesis; (1979); p. 356 View in Reaxys Tolbert; Houston; Journal of Organic Chemistry; vol. 28; (1963); p. 695,697 View in Reaxys 7 : Preparation of (2-formylpyridin-3-yl)carbamic acid 2-(TMSE-phosphonooxy)benzyl esters (23, 28a-k) (ozonolysis) Example 7 Preparation of (2-formylpyridin-3-yl)carbamic acid 2-(TMSE-phosphonooxy)benzyl esters (23, 28a-k) (ozonolysis) General Procedure. The corresponding 2-styrylpyridine (22 or 27a-k, 10 mmol) was dissolved in dichloromethane (50 mL) and ethanol (40 mL). The light yellow solution was ozonized at -50° C. till the solution turned to light blue. Nitrogen gas was bubbled through the solution for 30 min to expel excess ozone. To the solution was then added dimethyl sulfide (5 mL), and the mixture was stirred for 2 h at room temperature. The solvent was evaporated under reduced pressure, and the residual product was purified by FCC (1:9 v/v ethyl acetate-hexane) to afford the corresponding pyridine-2-carboxaldehyde (23 or 28a-k). Patent; Doyle, Terrence W.; Karra, Srinivasa; Li, Zujin; Lin, Xu; Mao, John; Qiao, Qi; Xu, Yang; US2002/119955; (2002); (A1) English View in Reaxys 27 : Preparation of Pyridine Aldehyde (18) (Scheme 5) EXAMPLE 27 Preparation of Pyridine Aldehyde (18) (Scheme 5) Following the procedure outlined in reaction Scheme and the description thereof, the Example 27 aldehyde is obtained. An example of a typical preparation of the aldehyde is set out below. To a 500 mL round bottom flask equipped with a magnetic stirrer and a nitrogen inlet was charged compound (17) (Scheme 5) (50 g, 128.4 mmol) (prepared as described in Example 2 Parts A, B and C except methyl isobutyryl acetate is substituted for ethyl isobutyryl acetate) and toluene (170 mL). The mixture is stirred at 20-25° C. until a clear solution is obtained. A solutin of 65percent Red-Al in toluene (57.8 mL, 192.6 mmol) is added and the reaction mixture is heated to 80° C. until complete as determined by HPLC. The reaction mixture is cooled to 20° C. and quenched by pouring it into cold (0-5° C.) 20percent HCl (495 mL). Phases are separated and the spent toluene phase is discarded. The pH of the aqueous phase is adjusted from <0 to 4-5 with 10N NaOH. Ethyl acetate (500 mL) is added and the pH adjustment continued to 7-8. The phases are separated. The aqueous phase is extracted with additional ethyl acetate (2*500 mL). The combined rich ethyl acetate solution is washed with water (3*250 mL) and concentrated under reduced pressure to ~465 mL. This solution is carried through to the next oxidation step. The rich ethyl acetate solution is charged from above into a three neck 1-L flask equipped with mechanical stirring, temperature controller, and addition funnel and cooled to 0-5° C. To the slurry, potassium bromide (1.53 g, 12.8 mmol) and TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) (0.20 g, 1.28 mmol) are added. The pH of NaOCl (sodium hypochlorite) solution (212.1 mL) is adjusted to ~9.1 and added to the slurry at a rate such that the temperature remained at 0-5° C. Stirring is continued at 0-5° C. until the reaction is complete as determined by HPLC. The aqueous phase is extracted with EtOAc (2*200 mL).

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The combined rich organic phase is washed with a 1:1 solution of sat. aq. Na2S2O3 (sodium thiosulfate) (75 mL) and water (75 mL) followed by wash of the rich organic phase with 1N NaOH (250 mL). The rich organic phase is washed with water (250 mL) and concentrated to ~100 mL under reduced pressure. Isopropanol (IPA) (400 mL) is added and the resulting mixture is heated to reflux (80-85° C.). The solution is distilled to a volume of ~250 mL. Water (50 mL) is added and the crystal slurry is stirred at 70-80° C. for 1 h then allowed to cool to 20-25° C. over at least 1 h. The slurry is held at 20-25° C. for at least 1 h before collecting the solid by filtration on a Buchner funnel. The cake is washed with cold (0° C.) IPA/water (4:1) (2*50 mL) and dried to a constant weight under vacuum at 40° C. to afford title aldehyde. Patent; Robl, Jeffrey A.; Chen, Bang-Chi; Sun, Chong-Qing; US2002/94977; (2002); (A1) English View in Reaxys Patent; Bristol-Myers Squibb Company; US6627636; (2003); (B2) English View in Reaxys The remaining teabags of amino acid on resin were each reacted as above in separate reactions with the following 94 aldehydes such that all combinations of 4-carboxy disubstituted dihydroisoquinolones were formed as indicated in the following (R2) list: ... 2-chloro-5-nitrobenzaldehyde, 2-chloro-6-fluorobenzaldehyde, 2-cyanobenzaldehyde, 2-fluorobenzaldehyde, 2-furaldehyde, 2-imidazolecarboxaldehyde, 2-methoxybenzaldehyde (o-anisaldehyde), 2-naphthaldehyde, 2-pyridinecarboxaldehyde, 2-quinolinecarboxaldehyde, 2-thiophenecarboxaldehyde, 3,4-(methylenedioxy)benzaldehyde (piperonal), 3,4-dibenzyloxybenzaldehyde, 3,4-dichlorobenzaldehyde, ... Patent; Basu; Amaresh; Gahman; Timothy C.; Girten; Beverly E.; Griffith; Michael C.; Hecht; Curtis C.; Kiely; John S.; Slivka; Sandra R.; US6127381; (2000); (A) English View in Reaxys 6.24 g (90%)

Synthesis of Pyridine Carboxaldehyde 21 Synthesis of Pyridine Carboxaldehyde 21 A methanol (140 mL) and dichloromethane (55 mL) solution of 5 (10.0 g, 41.84 mmol) was subjected to ozonalysis at -78° C. for 1 hr. The greenish solution was then quenched with dimethylsulfide (10 mL) at -78 ° C. The reaction mixture was allowed to stirred at rt overnight. The solvent was removed in vacuo to give a residue, which was purified on silica gel to provide 6.24 g (90percent) of the aldehyde 21 as a off-white solid. 1 H NMR of 21 (CDCl3): β 10.35 (s, 1H), 8.89-8.91 (m, 1H), 8.10-8.13 (m, 1H), 7.57-7.61 (m, 1H), 4.00 (s, 3H). Patent; Vion Pharmaceuticals, Inc.; US5767134; (1998); (A) English View in Reaxys The following list of compounds exemplifies aromatic and heterocyclic aldehydes useful in carrying out the first step of the processes of this invention leading to the compounds of Formula I. Benzaldehyde, ... 5-Methoxyindole-3-carboxaldehyde, 4-(N-Methylbenzylamino)benzaldehyde, Indole-3-carboxaldehyde, N-Methylpyrrole-2-carboxaldehyde, 2-Pyridinecarboxaldehyde, 3-Pyridinecarboxaldehyde, 4-Pyridinecarboxaldehyde, Pyrrole-2-carboxaldehyde, ... Patent; The Hilton-Davis Chemical Co.; US4595768; (1986); (A) English View in Reaxys

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The general procedure of Example 2 is repeated, except that the 3-nitrobenzaldehyde utilized therein is replaced in successive runs by an equimolar amount of ... (o) 5-bromo-2-furaldehyde, (p) 2-furaldehyde, (q) indole-3-carboxaldehyde, (r) 5-nitro-2-furaldehyde, (s) 2-pyridinecarboxaldehyde, (t) 3-pyridinecarboxaldehyde, (u) 2-thiophenecarboxaldehyde, (v) 3-thiophenecarboxaldehyde, ... Patent; Nelson Research and Development Co.; US4652573; (1987); (A) English View in Reaxys The following list of compounds exemplifies aliphatic, aromatic and heterocyclic aldehydes useful in carrying out the first step of the processes of this invention leading to the compounds of Formulas I, XI, XV and XVI. Benzaldehyde, ... 5-methoxyindole-3-carboxaldehyde, 4-(N-Methylbenzylamino)benzaldehyde, Indole-3-carboxaldehyde, N-Methylpyrrole-2-carboxaldehyde, 2-Pyridinecarboxaldehyde, 3-Pyridinecarboxaldehyde, 4-Pyridinecarboxaldehyde, Pyrrole-2-carboxaldehyde, ... Patent; Sterling Drug Inc.; US4257954; (1981); (A) English View in Reaxys e. 3'-(4-pyridyl)-spiro[6,7-methylenedioxy-1,2,3,4-tetrahydronaphalene-2,2' oxirane]-1-one (m.p. 166°-168°C) respectively. When an equivalent amount of ... h. 2 -pyrrolealdehyde; i. pyridine-2-carboxaldehyde; j. pyridine-3-carboxaldehyde; ... Patent; Sandoz, Inc.; US3932430; (1976); (A) English View in Reaxys Following essentially the same procedure as above but using an equivalent amount of ... i. pyridine-4-carboxaldehyde; j. pyridine-3-carboxaldehyde or k. pyridine-2-carboxaldehyde Patent; Sandoz, Inc.; US3932430; (1976); (A) English View in Reaxys Examples of aldehydes suitable for the purposes of the present invention include: ... 2,6-dichlorobenzaldehyde; 1-hydroxy-4-chloro-2-naphthaldehyde; 2-pyridinealdehyde; 4-chlorobenzaldehyde. Patent; GREAT LAKES CHEMICAL ITALIA S.r.l.; EP438819; (1991); (A1) English View in Reaxys Examples of aldehydes suitable for the purposes of the present invention include:

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... 4-N,N-diethylaminobenzaldehyde 3-indolealdehyde; 2,6-dichlorobenzaldehyde; 1-hydroxy-4-chloro-2-naphthaldehyde; 2-pyridinealdehyde; 4-chlorobenzaldehyde. Patent; Enichem Synthesis S.p.A.; US5225563; (1993); (A) English View in Reaxys 27 : Preparation of Pyridine Aldehyde (18) (Scheme 5) EXAMPLE 27 Preparation of Pyridine Aldehyde (18) (Scheme 5) Following the procedure outlined in reaction Scheme 5 and the description thereof, the Example 27 aldehyde is obtained. An example of a typical preparation of the aldehyde is set out below. To a 500 mL round bottom flask equipped with a magnetic stirrer and a nitrogen inlet was charged compound (17) (Scheme 5) (50 g, 128.4 mmol) (prepared as described in Example 2 Parts A, B and C except methyl isobutyryl acetate is substituted for ethyl isobutyryl acetate) and toluene (170 mL). The mixture is stirred at 20-25° C. until a clear solution is obtained. A solutin of 65percent Red-Al in toluene (57.8 mL, 192.6 mmol) is added and the reaction mixture is heated to 80° C. until complete as determined by HPLC. The reaction mixture is cooled to ~20° C. and quenched by pouring it into cold (0-5° C.) 20percent HCl (495 mL). Phases are separated and the spent toluene phase is discarded. The pH of the aqueous phase is adjusted from <0 to 4-5 with 10N NaOH. Ethyl acetate (500 mL) is added and the pH adjustment continued to 7-8. The phases are separated. The aqueous phase is extracted with additional ethyl acetate (2*500 mL). The combined rich ethyl acetate solution is washed with water (3*250 mL) and concentrated under reduced pressure to ~465 mL. This solution is carried through to the next oxidation step. The rich ethyl acetate solution is charged from above into a three neck 1-L flask equipped with mechanical stirring, temperature controller, and addition funnel and cooled to 0-5° C. To the slurry, potassium bromide (1.53 g, 12.8 mmol) and TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) (0.20 g, 1.28 mmol) are added. The pH of NaOCl (sodium hypochlorite) solution (212.1 mL) is adjusted to ~9.1 and added to the slurry at a rate such that the temperature remained at 0-5° C. Stirring is continued at 0-5° C. until the reaction is complete as determined by HPLC. The aqueous phase is extracted with EtOAc (2*200 mL). The combined rich organic phase is washed with a 1:1 solution of sat. aq. Na2S2O3 (sodium thiosulfate) (75 mL) and water (75 mL) followed by wash of the rich organic phase with 1N NaOH (250 mL). The rich organic phase is washed with water (250 mL) and concentrated to ~100 mL under reduced pressure. Isopropanol (IPA) (400 mL) is added and the resulting mixture is heated to reflux (80-85° C.). The solution is distilled to a volume of ~250 mL. Water (50 mL) is added and the crystal slurry is stirred at 70-80° C. for 1 h then allowed to cool to 20-25° C. over at least 1 h. The slurry is held at 20-25° C. for at least 1 h before collecting the solid by filtration on a Buchner funnel. The cake is washed with cold (0° C.) IPA/water (4:1) (2*50 mL) and dried to a constant weight under vacuum at 40° C. to afford title aldehyde. Patent; Robl, Jeffrey A.; Chen, Bang-Chi; Sun, Chong-Qing; US2004/92573; (2004); (A1) English View in Reaxys 1 : Preparation of 1-benzylpyrrole-2-carbaldehyde, 1-benzylpiperidine-2-carbaldehyde, 1-benzylpyrazole-2-carbaldehyde, pyridine-2-carbaldehyde, pyrimidine-2-carbaldehyde. General procedure: Take 10g 1-benzylpyrrole dissolved in 100ml DCM, cooled to -75 , put n-butyl lithium, stirring 1h, dropping piperidine-1-formaldehyde, dropping slowly slow to -30 , stirring 5h, reaction End. Water quenching reaction. The extraction reaction was concentrated and the DCM layer was concentrated to give the product 1-benzylpyrrole-2-carbaldehyde. Stage 1: With n-butyllithium in dichloromethane, Time= 1h, T= -75 °C Stage 2: in dichloromethane, Time= 5h, T= -30 °C , Reagent/catalyst

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Patent; Jiangsu Siweisen Bio-pharmaceutical Engineering Research Center Co., Ltd.; Zhangjiagang Weisheng Bio-pharmaceutical Co., Ltd.; Wuyang Weisen Bio-pharmaceutical Co., Ltd.; Zhang Mei; Peng Xuedong; Zhao Jinzhao; Huang Xianming; (7 pag.); CN107033058; (2017); (A) Chinese View in Reaxys Examples of the compound represented by the general formula (4) include, but are not limited to, acetaldehyde, propionaldehyde, butanal, pentanal, hexanal, heptanal, octanal, phenylacetaldehyde, 3-phenylpropionaldehyde, 4phenylbutanal, 5-phenylpentanal, benzaldehyde, ... 2-nitrobenzaldehyde, 3-nitrobenzaldehyde, 4-nitrobenzaldehyde, 2-cyanobenzaldehyde, 3-cyanobenzaldehyde, 4-cyanobenzaldehyde, 2-methylbenzaldehyde, 3-methylbenzaldehyde, 4-methylbenzaldehyde, 2-methoxybenzaldehyde, 3-methoxybenzaldehyde, 4-methoxybenzaldehyde, 2-pyridinecarboxaldehyde, 3-pyridinecarboxaldehyde, 4-pyridinecarboxaldehyde, 2-thiophenecarboxaldehyde, 3-thiophenecarboxaldehyde, 4-thiophenecarboxaldehyde benzylacetone, 5-phenyl-2-propanone, acetophenone, ... Patent; IHARA CHEMICAL INDUSTRY CO., LTD.; KUMIAI CHEMICAL INDUSTRY CO., LTD.; KAWAZOE, Kentaro; YOSHIOKA, Kotaro; (107 pag.); US2017/197920; (2017); (A1) English View in Reaxys

Rx-ID: 42304115 View in Reaxys 8/115 Yield

Conditions & References

83 %

Stage 1: With palladium diacetate, acetic anhydride, tricyclohexylphosphine in N,N-dimethyl-formamide, Time= 1h, T= 30 °C , Inert atmosphere, Green chemistry Stage 2: With triethylamine in N,N-dimethyl-formamide, Time= 6h, T= 80 °C , Inert atmosphere, Green chemistry Qi, Xinxin; Li, Chong-Liang; Wu, Xiao-Feng; Chemistry - A European Journal; vol. 22; nb. 17; (2016); p. 5835 - 5838 View in Reaxys

52 %

With palladium diacetate, triethylamine, dicyclohexyl-carbodiimide, tricyclohexylphosphine in N,N-dimethyl-formamide, Time= 10h, T= 60 °C , Inert atmosphere, Sealed tube Wu, Fu-Peng; Peng, Jin-Bao; Meng, Ling-Shen; Qi, Xinxin; Wu, Xiao-Feng; ChemCatChem; vol. 9; nb. 16; (2017); p. 3121 - 3124 View in Reaxys O

O N

N N

O N

OH N H

Rx-ID: 45460242 View in Reaxys 9/115 Yield

Conditions & References

36 %, 30 %, Typical procedure 23 % General procedure: To a solution of 2-(2’-pyridyl)-1,3-oxazoline (1, 37 mg, 0.25 mmol) and pyridine (80 L, 1.0 mmol) in H2O (6 mL), was added pyridinium hydrobromide perbromide (320 mg, 1.0 mmol) at room temperature. After stirring for 23 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3 (10 mL), 1.0 M NaHCO3 (15 mL) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M aq Na2S2O3 and successively washed with saturated aq NaCl, and dried over MgSO4. After removal ofsolvent in vacuo, the residue was purified by column chromatography on silica gel (Wako C-200) with CCl4, CCl4CHCl3 (2:1 v/v). Cyanomethyl 2-pyridinecarboxylate (2, 38 mg, 0.23 mmol) was obtained in 92percent yield. With pyridine, pyridinium perbromide hydrobromide, water, Time= 14h, T= 20 °C Sayama, Shinsei; Heterocycles; vol. 94; nb. 6; (2017); p. 1133 - 1142 View in Reaxys

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H 2N

O N

Rx-ID: 46282187 View in Reaxys 10/115 Yield

Conditions & References

10 %, 78 %

With oxygen, copper diacetate, trifluoroacetic acid in N,N-dimethyl-formamide, Time= 1h, T= 120 °C Dai, Chenshu; Deng, Siqi; Zhu, Qiuhua; Tang, Xiaodong; RSC Advances; vol. 7; nb. 70; (2017); p. 44132 - 44135 View in Reaxys

Rx-ID: 46695159 View in Reaxys 11/115 Yield

Conditions & References Reaction Steps: 3 1: 5 h / 90 °C 2: potassium hydoxide / 5 h 3: pyridinium chlorochromate / 1 - 25 °C With pyridinium chlorochromate, potassium hydoxide Patent; Liu Ruihai; (6 pag.); CN107286080; (2017); (A) Chinese View in Reaxys

NH 2

Rx-ID: 45858 View in Reaxys 12/115 Yield 80 %

Conditions & References With 1,4-bis(triphenylphosphonium)butane cerium nitrate in water, acetic acid, Time= 0.583333h, Reflux Heidari, Mohammad; Ershadifar, Mohammad; Hamid, Masoumeh; Badri, Rashid; Journal of the Chemical Society of Pakistan; vol. 38; nb. 5; (2016); p. 944 - 947 View in Reaxys Aufbewahren unter Luftzutritt Graf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 146; (1936); p. 88,102 View in Reaxys With riboflavin tetraacetate in dimethylsulfoxide-d6, water-d2, Time= 0.166667h, Irradiation, In air Lechner, Robert; Koenig, Burkhard; Synthesis; nb. 10; (2010); p. 1712 - 1718; Art.No: Z01810SS View in Reaxys

N O

Rx-ID: 5184004 View in Reaxys 13/115 Yield 95 %

Conditions & References With dihydrogen peroxide in water, Time= 4h, T= 100 °C Rajabi, Fatemeh; Karimi, Nafiseh; Saidi, Mohammad Reza; Primo, Ana; Varma, Rajender S.; Luque, Rafael; Advanced Synthesis and Catalysis; vol. 354; nb. 9; (2012); p. 1707 - 1711 View in Reaxys

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82 %

With sodium periodate, C53H44As2N2O3Ru in water, ethyl acetate, acetonitrile, Time= 0.5h, T= 25 °C Manikandan, Thimma Sambamoorthy; Ramesh, Rengan; Semeril, David; RSC Advances; vol. 6; nb. 99; (2016); p. 97107 97115 View in Reaxys

63 %

Stage 1: With oxygen, ozone in dichloromethane, T= -78 °C Stage 2: With poly(ethylene glycol)-triphenylphosphine in dichloromethane, T= -78 - 20 °C Sieber, Frank; Wentworth Jr., Paul; Janda, Kim D.; Molecules; vol. 5; nb. 8; (2000); p. 1018 - 1032 View in Reaxys With p-PPh2-C6H4-(OCH2CH2)n-O-C6H4-PPh2-p, ozone, 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, 2 h, Yield given, Multistep reaction Sieber, Frank; Wentworth Jr., Paul; Toker, Jonathan D.; Wentworth, Anita D.; Metz, William A.; Reed, Neal N.; Janda, Kim D.; Journal of Organic Chemistry; vol. 64; nb. 14; (1999); p. 5188 - 5192 View in Reaxys Microwave assisted oxidation of benzyl alcohol and aromatic alkenes General procedure: The reaction was carried out in a CEM Discover microwave reactor equipped with a PC-controlled interface. The method was power controlled in which samples (vessel size 10 mL) were irradiated at 300 W (maximum power output) to achieve different temperatures. In a typical reaction, a mixture containing 2 mmol of substrate, 0.4 mL of H2O2 (50 wt.percent), 2 mL of water and 0.05 g of catalyst was microwaved in a CEM-DISCOVER reactor for different times of reaction (typically between 3 and 15 min) at 300 W, reaching a maximum temperature between 100 and 120 °C (average temperature 100 °C). Dodecane was added to the mixture as internal standard. The microwave method was power-controlled and reactions were carried out in closed vessel mode (pressure 120–200 psi-8.3 to 13.4 bar-developed in the system). Upon reaction completion (in both cases), samples were collected, extracted with an organic solvent (typically toluene) and subsequently analysed by GC and GC/MS in an Agilent 6890N fitted with an HP-5 capillary column (30 m × 0.32 mm × 0.25 μm) and a flame ionization detector (FID). With dihydrogen peroxide in water, T= 110 - 120 °C , p= 6205.94 - 10343.2Torr , Microwave irradiation, Sealed tube, Green chemistry Balu, Alina Mariana; Lin, Carol Sze Ki; Liu, Hongli; Li, Yingwei; Vargas, Carolina; Luque, Rafael; Applied Catalysis A: General; vol. 455; (2013); p. 261 - 266 View in Reaxys N N

N O

Rx-ID: 42199567 View in Reaxys 14/115 Yield

Conditions & References With [2,2]bipyridinyl, ammonium hydroxide, copper(l) iodide, N,N-dimethyl-(4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl)dodecylammonium bromide, oxygen in neat (no solvent), Time= 10h, T= 55 °C , p= 750.075Torr , Green chemistry, Overall yield = 63.1 percent Zhang, Yuecheng; Huang, Rong; Gao, Baosheng; Zhao, Jiquan; Catalysis Letters; vol. 146; nb. 1; (2016); p. 220 - 228 View in Reaxys

N N

N O

O OH

Rx-ID: 42202265 View in Reaxys 15/115 Yield 88 %

Conditions & References With copper(II) nitrate hexahydrate in dichloromethane, water, Time= 3h, T= 20 °C Zhen, Maomin; Peng, Yanqing; Organic and Biomolecular Chemistry; vol. 14; nb. 13; (2016); p. 3443 - 3449 View in Reaxys

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O O

O N

N H

Rx-ID: 42346760 View in Reaxys 16/115 Yield

Conditions & References

60 %

General procedure for the cleavage of hydrazones by bismuth oxychloride: General procedure: A solution of the hydrazone (1 mmol) in acetonitrile (10 mL) was refluxed for 10 min.Then BiOCl (1 mmol) was added to the solution and the mixture was refluxed for theappropriate time, as indicated in Table I. After completion of the reaction (TLC monitored),the reaction mixture was cooled to room temperature and H2O (1 mmol) was added and themixture stirred for 10 min. Then the solvent was evaporated and CHCl3 or THF was added.After stirring the mixture for 10 min, the solid residue was filtered off and washed with CHCl3or THF (10 mL). Evaporation of the solvent gave the pure carbonyl products in excellentyields. With bismuth (III) oxychloride in water, acetonitrile, Time= 4.83333h, Reflux Manesh, Abbas Amini; Azarin, Khadijeh; Journal of the Serbian Chemical Society; vol. 81; nb. 2; (2016); p. 125 - 131 View in Reaxys O

Rx-ID: 39367102 View in Reaxys 17/115 Yield

Conditions & References General Procedure for the Formation of Aldehyde Bisulfite Adducts. General procedure: The following procedure for the formation of the bisulfite adduct of 5-bromonicotinaldehyde is representative. To an oven-dried and argon cooled 25-mL round-bottom flask equipped with a stir bar and septa was added 5-bromo-Nmethoxy-N-methylnicotinamide (0.490 g,2 mmol) followed by THF (1.7 mL). Chloromagnesium dimethylaminoborohydride(MgAB, 2 mL, 1 m, 2 mmol) was then added dropwise via a syringe. The reaction wasmonitored by TLC (Hex/EtOAc, 1:1). After 30 min, the reaction solution was added dropwise to a solution of acetaldehyde (2 mmol) and acetic acid (2 mmol) in pentane (10mL). After 15 min, saturated aqueous NH4Cl (2 mL) was added. The organic layer was separated and the aqueous phase was extracted with Et2O (2 x 10 mL). The combinedorganic layers was washed with 1M HCl (10 mL), dried with magnesium sulfate, and concentrated under reduced pressure to yield orange oil. To a round-bottom flask equipped with a magnetic stir bar was charged the crude aldehyde (2 mmol) followed byEtOH (3 mL) and EtOAc (5 mL) and cooled with an ice bath. A saturated aqueous solution of NaHSO3 (1 mL) was added with stirring. After 4 h, the solid bisulfite adduct was isolated by vacuum filtration, washed with Et2O (3 × 5 mL) and dried under vacuumto yield a white solid (0.407g, 70percent). Thermal decomposition of the compounds prohibited melting point measurement,7 and elemental analysis gave unreliable results, asis typical of bisulfite adducts. For other adducts prepared by this method see Table 2. Stage 1: With chloromagnesium dimethylaminoborohydride in tetrahydrofuran, Time= 0.5h, T= 25 °C , Inert atmosphere Stage 2: With acetaldehyde, acetic acid in tetrahydrofuran, pentane, Time= 0.25h, Inert atmosphere Bailey, Christopher L.; Clary, Jacob W.; Tansakul, Chittreeya; Klabunde, Lucas; Anderson, Christopher L.; Joh, Alexander Y.; Lill, Alexander T.; Peer, Natalie; Braslau, Rebecca; Singaram, Bakthan; Tetrahedron Letters; vol. 56; nb. 5; (2015); p. 706 - 709 View in Reaxys

O N

Rx-ID: 39822517 View in Reaxys 18/115 Yield 49 %

Conditions & References With methanesulfonic acid in [D3]acetonitrile, Time= 24h, T= 20 °C , Molecular sieve Zhou, Yuntao; Ye, Hebo; You, Lei; Journal of Organic Chemistry; vol. 80; nb. 5; (2015); p. 2627 - 2633 View in Reaxys

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O N

Rx-ID: 39822518 View in Reaxys 19/115 Yield

Conditions & References

41 %

With methanesulfonic acid in [D3]acetonitrile, Time= 24h, T= 20 °C , Molecular sieve Zhou, Yuntao; Ye, Hebo; You, Lei; Journal of Organic Chemistry; vol. 80; nb. 5; (2015); p. 2627 - 2633 View in Reaxys

O N

Rx-ID: 39822519 View in Reaxys 20/115 Yield

Conditions & References

49 %

O N

Rx-ID: 39822520 View in Reaxys 21/115 Yield

Conditions & References

67 %

O N

Rx-ID: 39822522 View in Reaxys 22/115 Yield

Conditions & References

84 %

N N

O N

Rx-ID: 39822523 View in Reaxys 23/115

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Yield

Conditions & References

O N

Rx-ID: 39822525 View in Reaxys 24/115 Yield

Conditions & References

29 %

N N

Rx-ID: 39822526 View in Reaxys 25/115 Yield

Conditions & References

N O N

Rx-ID: 39822527 View in Reaxys 26/115 Yield

Conditions & References

N N

N O

O N

Rx-ID: 39822529 View in Reaxys 27/115 Yield 5%

Conditions & References With methanesulfonic acid in [D3]acetonitrile, Time= 24h, T= 20 °C , Molecular sieve

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Zhou, Yuntao; Ye, Hebo; You, Lei; Journal of Organic Chemistry; vol. 80; nb. 5; (2015); p. 2627 - 2633 View in Reaxys

N O

N O N

Rx-ID: 39822531 View in Reaxys 28/115 Yield

Conditions & References

N O N

Rx-ID: 39822532 View in Reaxys 29/115 Yield

Conditions & References

N O

N O N

Rx-ID: 39822533 View in Reaxys 30/115 Yield

Conditions & References

16 %

O O N

Rx-ID: 39822534 View in Reaxys 31/115 Yield 53 %

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O N

Rx-ID: 39822535 View in Reaxys 32/115 Yield

Conditions & References

41 %

O N N

Rx-ID: 39822536 View in Reaxys 33/115 Yield

Conditions & References

35 %

Rx-ID: 40666587 View in Reaxys 34/115 Yield

Conditions & References in N,N-dimethyl-formamide, Time= 8h, T= 120 °C , Inert atmosphere Zhu, Yaoqin; Shen, Mengnan; Xia, Yonggen; Lu, Ming; Applied Organometallic Chemistry; vol. 29; nb. 3; (2015); p. 152 156 View in Reaxys

OH N

N O

Rx-ID: 8610077 View in Reaxys 35/115 Yield 89 %

Conditions & References With zinc(II) nitrate, silica gel, Time= 0.0666667h, Irradiation, deoxymation Tamami; Kiasat; Synthetic Communications; vol. 30; nb. 22; (2000); p. 4129 - 4135 View in Reaxys

79 %

With cellulose supported Cu-nanoparticles in water, Time= 0.0833333h, T= 80 °C , Microwave irradiation, Green chemistry Baruah, Diganta; Saikia, Ujwal Pratim; Pahari, Pallab; Dutta, Dipak Kumar; Konwar, Dilip; RSC Advances; vol. 4; nb. 103; (2014); p. 59338 - 59343 View in Reaxys

71 %

With iodine, sodium dodecyl-sulfate in water, Time= 4h, T= 25 - 40 °C Gogoi, Pranjal; Hazarika, Parasa; Konwar, Dilip; Journal of Organic Chemistry; vol. 70; nb. 5; (2005); p. 1934 - 1936 View in Reaxys

58 %

With aluminum(III) nitrate nonahydrate, sodium bromide in dichloromethane, Time= 30.5h, T= 20 °C

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Ghorbani-Choghamarani, Arash; Zeinivand, Javad; Chinese Chemical Letters; vol. 21; nb. 9; (2010); p. 1083 - 1086 View in Reaxys

N O

N N

Rx-ID: 37172529 View in Reaxys 36/115 Yield

Conditions & References

20 %, 29 %, With palladium on activated charcoal, 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile, Time= 20h, T= 80 °C , Autoclave 33 % Yu, Bo; Zhao, Yanfei; Zhang, Hongye; Xu, Jilei; Hao, Leiduan; Gao, Xiang; Liu, Zhimin; Chemical Communications; vol. 50; nb. 18; (2014); p. 2330 - 2333 View in Reaxys O N

Rx-ID: 38671869 View in Reaxys 37/115 Yield

Conditions & References Reaction Steps: 2 1: triethylsilane; triethylamine / tetrahydrofuran / 1 h / 20 °C 2: triethylsilane / tetrahydrofuran / 1 h With triethylsilane, triethylamine in tetrahydrofuran, 2: |Fukuyama Reduction Asadi, Mousa; Bonke, Shannon; Polyzos, Anastasios; Lupton, David W.; ACS Catalysis; vol. 4; nb. 6; (2014); p. 2070 - 2074 View in Reaxys

O N S

N O

Rx-ID: 38671878 View in Reaxys 38/115 Yield

Conditions & References

43 %

With triethylsilane in tetrahydrofuran, Time= 1h, Fukuyama Reduction, Reagent/catalyst Asadi, Mousa; Bonke, Shannon; Polyzos, Anastasios; Lupton, David W.; ACS Catalysis; vol. 4; nb. 6; (2014); p. 2070 - 2074 View in Reaxys O

N OH

Rx-ID: 27939954 View in Reaxys 39/115 Yield

Conditions & References With tert.-butylhydroperoxide, [O-Cu4(triethanolamine)4(BOH)4][BF4]2 in acetonitrile, Time= 6h, T= 69.84 °C , Title compound not separated from byproducts. Zhu, Mingxia; Li, Bodong; He, Ping; Wei, Xin; Yuan, Youzhu; Tetrahedron; vol. 64; nb. 39; (2008); p. 9239 - 9243

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View in Reaxys With copper(ll) sulfate pentahydrate, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 2-N-(p-fluorophenyl)-pyrrolecarbaldimine, dihydrogen peroxide, potassium carbonate in water, Time= 1h, T= 60 °C Ahmad, Jahir Uddin; Raeisaenen, Minna T.; Leskelae, Markku; Repo, Timo; Applied Catalysis A: General; vol. 411-412; (2012); p. 180 - 187 View in Reaxys 52 %Chromat., 43 %Chromat.

With sodium hypochlorite in 1,2-dimethoxyethane, water, Time= 4h, T= 20 °C Fukuda, Naohiro; Kajiwara, Takeshi; Katou, Tomoaki; Majima, Keisuke; Ikemoto, Tomomi; Synlett; vol. 24; nb. 11; (2013); p. 1438 - 1442; Art.No: ST-2013-U0273-L View in Reaxys

H H N H

H+

O N

H 2N

O H

N H

Rx-ID: 35375238 View in Reaxys 40/115 Yield

Conditions & References With water, toluene-4-sulfonic acid in propan-1-ol, Time= 0.75h, Solvent Bunzen, Hana; Kolehmainen, Erkki; Molecules; vol. 18; nb. 4; (2013); p. 3745 - 3759 View in Reaxys

P (v6) (v4)

(v3)

(v4)

H O

N (v4)

(v1) – (v3) Cl (v4) O

(v3)

(v4)

O C HO

N– (v3)

Ru 2+ Cl – (v6) (v3)P(v4)

P (v1)

C Ru 2+(v3) OC-6 (v6) N – P (v4)

O (v3)

racemate

Rx-ID: 35427294 View in Reaxys 41/115 Yield 40 %

Conditions & References in toluene, Time= 0.666667h, Inert atmosphere, Reflux Biswas, Manas Kumar; Patra, Sarat Chandra; Maity, Amarendra Nath; Ke, Shyue-Chu; Weyhermueller, Thomas; Ghosh, Prasanta; Chemical Communications; vol. 49; nb. 40; (2013); p. 4522 - 4524 View in Reaxys

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O N

N S O

Rx-ID: 36051547 View in Reaxys 42/115 Yield

Conditions & References

45 %

With triethylsilane, palladium diacetate, sodium carbonate, 1,4-di(diphenylphosphino)-butane in N,N-dimethyl-formamide, T= 70 °C , Inert atmosphere, Sealed tube Ueda, Tsuyoshi; Konishi, Hideyuki; Manabe, Kei; Angewandte Chemie - International Edition; vol. 52; nb. 33; (2013); p. 8611 - 8615; Angew. Chem.; vol. 125; nb. 33; (2013); p. 8773 - 8777,5 View in Reaxys N N

N O

N N

Rx-ID: 36937559 View in Reaxys 43/115 Yield

Conditions & References T= 800 °C , p= 0.0003Torr , Gas phase, regioselective reaction Vu, Thien Y; Chrostowska, Anna; Huynh, Thi Kieu Xuan; Khayar, Said; Dargelos, Alain; Justyna, Katarzyna; Pasternak, Beata; Lesniak, Stanislaw; Wentrup, Curt; Chemistry - A European Journal; vol. 19; nb. 44; (2013); p. 14983 - 14988 View in Reaxys O

Rx-ID: 22169464 View in Reaxys 44/115 Yield 94 %

Conditions & References With n-butyllithium, diisobutylaluminium hydride, tert-butyl alcohol in tetrahydrofuran, hexane, T= 0 °C De Munoz, Juan M.; Alcazar, Jesus; De La Hoz, Antonio; Diaz-Ortiz, Angel; European Journal of Organic Chemistry; nb. 2; (2012); p. 260 - 263 View in Reaxys Reaction Steps: 2 1: diethyl ether; lithium alanate 2: lead (IV)-acetate; benzene With lead(IV) acetate, lithium aluminium tetrahydride, diethyl ether, benzene Micovic; Mihailovic; Recueil des Travaux Chimiques des Pays-Bas; vol. 71; (1952); p. 970,974 View in Reaxys 17.a : 2-Pyridyl-carbaldehyde EXAMPLE 17a 2-Pyridyl-carbaldehyde The solution of 50 ml (370 mmol) of 2-picolinic acid ethyl ester in 1 l of anhydrous dichloromethane is cooled under an atmosphere of dry argon to -78° C., mixed with 500 ml of a 1.2 molar solution of diisobutylaluminum hydride in toluene and stirred for one more hour. It is mixed with 152 ml of isopropanol, 253 ml of water, allowed to heat to 23° C. and stirred until a fine-grained precipitate has formed. After filtration and removal of the solvent, 32.6 g (304 mmol, 82percent) of the title compound is isolated as a pale yellow oil. 1H-NMR (CDCl ): β=7.52 (1H), 7.89 (1H), 7.99 (1H), 8.80 (1H), 10.10 (1H) ppm. 3 With diisobutylaluminium hydride in dichloromethane, water, isopropyl alcohol, toluene Patent; Schering AG; US6610736; (2003); (B1) English View in Reaxys

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Rx-ID: 32618211 View in Reaxys 45/115 Yield

Conditions & References

92 %

With thionyl chloride, dihydrogen peroxide in acetonitrile, Time= 0.0166667h, T= 25 °C Bahrami, Kiumars; Khodaei, Mohammad Mehdi; Tajik, Maryam; Shakibaian, Vida; Chinese Chemical Letters; vol. 23; nb. 1; (2012); p. 81 - 85 View in Reaxys

N O H

O N OH

Rx-ID: 33576849 View in Reaxys 46/115 Yield

Conditions & References With water Buchs, Barbara; Fieber, Wolfgang; Drahonovsky, Dusan; Lehn, Jean-Marie; Herrmann, Andreas; Chemistry and Biodiversity; vol. 9; nb. 4; (2012); p. 689 - 701 View in Reaxys

N O

Rx-ID: 33576852 View in Reaxys 47/115 Yield

N O

Rx-ID: 33644736 View in Reaxys 48/115 Yield

Conditions & References

17 %Chromat., 10 %Chromat., 86 %Chromat.

With manganese(IV) oxide, oxygen, urea, Time= 3h, T= 150 °C , p= 3800.26Torr , Autoclave Wang, Ye; Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 51; nb. 29; (2012); p. 7250 - 7253 View in Reaxys

N N

N O

Rx-ID: 1561119 View in Reaxys 49/115 Yield 73 %

Conditions & References With C13H26B(1-)*K(1+) in tetrahydrofuran, Time= 24h, Ambient temperature

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Cha, Jin Soon; Yoon, Sook; Tetrahedron Letters; vol. 30; nb. 28; (1989); p. 3677 - 3680 View in Reaxys 56 %

General Procedure: General procedure: Solutions of nitrile dissolved in Toluene (5 mL) and DIBAL (1 M) in Toluene were pumped at the appropriate flow rate and mixed in a 0.85 mL Microreactor Explorer Kit chip reactor. For longer residence times extra 20 ml tubing was added at the end of the reactor. The solution at the microreactor outlet was poured into a 1percent Sodium Tartrate solution at 0 °C. The crude solution was extracted with EtOAc. The extracts were dried over MgSO4, filtered and evaporated to yield the desired product. All products obtained and discussed in this work have been previously reported and characterized. Stage 1: With diisobutylaluminium hydride in toluene, Time= 0.222222h, T= 20 °C , Flow reactor Stage 2: With water, sodium L-tartrate in toluene, T= 0 °C , chemoselective reaction Munoz, Juan De M.; Alcazar, Jesus; De La Antonio, Hoz; Diaz-Ortiz, Angel; Tetrahedron Letters; vol. 52; nb. 46; (2011); p. 6058 - 6060 View in Reaxys N

N O

Rx-ID: 32522542 View in Reaxys 50/115 Yield

Conditions & References

19 %Chromat., 26 %Chromat.

With manganese(II) 5,10,15,20-tetrakis(N-ethylpyridinium-4-yl)porphyrin, dihydrogen peroxide in water, acetone, Time= 5h, T= 90 °C Ren, Qing-Gang; Zhou, Xian-Tai; Ji, Hong-Bing; Journal of Porphyrins and Phthalocyanines; vol. 15; nb. 3; (2011); p. 211 216 View in Reaxys

Rx-ID: 29981195 View in Reaxys 51/115 Yield

Conditions & References With copper(l) iodide, oxygen, palladium diacetate, Time= 24h, T= 120 °C , Autoclave Jiang, Huanfeng; Chen, Huoji; Wang, Azhong; Liu, Xiaohang; Chemical Communications; vol. 46; nb. 38; (2010); p. 7259 7261 View in Reaxys

N OH

N O

Rx-ID: 30027871 View in Reaxys 52/115 Yield

Conditions & References With manganese(II) nitrate hexahydrate, copper(II) nitrate trihydrate, toluene-4-sulfonic acid in β,β,β-trifluorotoluene, Time= 2.5h, T= 50 °C , In air, chemoselective reaction Tucker-Schwartz, Alexander K.; Garrell, Robin L.; Chemistry - A European Journal; vol. 16; nb. 42; (2010); p. 12718 12726 View in Reaxys

N OH

N O

N N

H N

N H

Rx-ID: 28409855 View in Reaxys 53/115

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Yield

Conditions & References

70 %

With zinc dibromide in toluene, Time= 2.5h, Reflux Cao, Hai Thuong; Gree, Rene; Tetrahedron Letters; vol. 50; nb. 13; (2009); p. 1493 - 1494 View in Reaxys

N C

Rx-ID: 9178039 View in Reaxys 54/115 Yield

Conditions & References

80 %

With palladium diacetate, hydrogen, triphenylphosphine, 2,4,6-trimethyl-pyridine, tributyl-amine in acetonitrile, Time= 18h, T= 120 °C , p= 22501.8Torr Holzapfel, Cedric W.; Ferreira, Alta C.; Marais, Wilhelmina; Journal of Chemical Research - Part S; nb. 5; (2002); p. 218 220 View in Reaxys

7 % Chromat.

With 4-methoxy-N'-tetramethylethylenediamine, hydrogen, catacxium A, palladium diacetate in toluene, Time= 16h, T= 100 °C , p= 3750.3Torr Klaus, Stefan; Neumann, Helfried; Zapf, Alexander; Struebing, Dirk; Huebner, Sandra; Almena, Juan; Riermeier, Thomas; Gross, Peter; Sarich, Martin; Krahnert, Wolf-Ruediger; Rossen, Kai; Beller, Matthias; Angewandte Chemie - International Edition; vol. 45; nb. 1; (2006); p. 154 - 158 View in Reaxys

100 %Chro- With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II), sodium carbonate in N,N-dimethyl-formamide, 1,3,5-trimat. methyl-benzene, Time= 18h, T= 90 °C , p= 2250.23Torr , Sealed tube Ashfield, Laura; Barnard, Christopher F. J.; Organic Process Research and Development; vol. 11; nb. 1; (2007); p. 39 - 43 View in Reaxys O

Rx-ID: 10456877 View in Reaxys 55/115 Yield

Conditions & References

25 %, 70 %

With 1H-imidazole, sodium periodate, MnCl-TPP-(PEO750)4 in water, acetonitrile, Time= 24h, T= 80 °C Liu, Shiuh-Tzung; Reddy, K. Venugopal; Lai, Rung-Yi; Tetrahedron; vol. 63; nb. 8; (2007); p. 1821 - 1825 View in Reaxys

N O

N S

Rx-ID: 11152415 View in Reaxys 56/115 Yield 73 %

Conditions & References With trifluoroacetic acid in water, acetonitrile, Time= 3h, T= 20 °C Mamane, Victor; Aubert, Emmanuel; Fort, Yves; Journal of Organic Chemistry; vol. 72; nb. 19; (2007); p. 7294 - 7300 View in Reaxys

N O

sulfur

CH2=CHMgX Rx-ID: 11346298 View in Reaxys 57/115

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Yield

Conditions & References Reaction Steps: 2 1.1: t-BuONa; (i-Pr)2NEt; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 85 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.1: 73 percent / PhI(COCF3)3; CF3CO2H / acetonitrile; H2O / 3 h / 20 °C With n-butyllithium, N-ethyl-N,N-diisopropylamine, trifluoroacetic acid, sodium t-butanolate in tetrahydrofuran, hexane, water, acetonitrile Mamane, Victor; Aubert, Emmanuel; Fort, Yves; Journal of Organic Chemistry; vol. 72; nb. 19; (2007); p. 7294 - 7300 View in Reaxys

N O

(v5)

Rx-ID: 10253229 View in Reaxys 58/115 Yield

Conditions & References With sulfuric acid in methanol, Time= 3h, Heating Goldeman, Waldemar; Olszewski, Tomasz K.; Boduszek, Bogdan; Sawka-Dobrowolska, Wanda; Tetrahedron; vol. 62; nb. 18; (2006); p. 4506 - 4518 View in Reaxys

N O

Rx-ID: 9633684 View in Reaxys 59/115 Yield

Conditions & References

14.5 %

With oxygen, CrV0.95P0.05O4, T= 300 °C , atmospheric pressure, Product distribution, Further Variations: Temperatures, Reagents Shishido; Song; Matsushita; Takaki; Takehira; Physical Chemistry Chemical Physics; vol. 5; nb. 12; (2003); p. 2710 - 2718 View in Reaxys F

F N

S O

Rx-ID: 9184079 View in Reaxys 60/115 Yield 80 %

Conditions & References With palladium diacetate, hydrogen, triphenylphosphine, 2,4,6-trimethyl-pyridine, tributyl-amine in acetonitrile, Time= 18h, T= 120 °C , p= 22501.8Torr Holzapfel, Cedric W.; Ferreira, Alta C.; Marais, Wilhelmina; Journal of Chemical Research - Part S; nb. 5; (2002); p. 218 220 View in Reaxys

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E N O N H

N O

P O

N H

Rx-ID: 24073881 View in Reaxys 61/115 Yield

Conditions & References

72%

7 : Preparation of (2-formylpyridin-3-yl)carbamic acid 2-(TMSE-phosphonooxy)benzyl esters (23, 28a-k) (ozonolysis) EXAMPLE 7 Preparation of (2-formylpyridin-3-yl)carbamic acid 2-(TMSE-phosphonooxy)benzyl esters (23, 28a-k) (ozonolysis) General Procedure. The corresponding 2-styrylpyridine (22 or 27a-k, 10 mmol) was dissolved in dichloromethane (50 mL) and ethanol (40 mL). The light yellow solution was ozonized at -50° C. till the solution turned to light blue. Nitrogen gas was bubbled through the solution for 30 min to expel excess ozone. To the solution was then added dimethyl sulfide (5 mL), and the mixture was stirred for 2 h at room temperature. The solvent was evaporated under reduced pressure, and the residual product was purified by FCC (1:9 v/v ethyl acetate-hexane) to afford the corresponding pyridine-2-carboxaldehyde (23 or 28a-k). (2-Formylpyridin-3-yl)carbamic acid 2-bis(2-trimethylsilylethyl)phosphonooxy-5-chlorobenzyl ester (23) Following the above procedure, 22 (2.4 g, 3.7 mmol) gave 23 (1.6 g, 72percent) as an oil: 1H NMR (300 MHz, CDCl ) β10.38 (br s, 1H), 9.90 (s, 1H), 8.67 (d, 1H), 8.28 (dd, 1H), 7.4-7.3 (m, 2H), 7.23 (dd, 1H), 7.13 (dd, 3 1H), 5.14 (s, 2H), 4.12 (m, 4H), 0.97 (m, 4H) and -0.14 (m, 18H). NMR (75 MHz, CDCl3) β197.0, 152.9, 147.3 (d), 143.7, 138.3, 136.7, 130.1, 129.6, 129.5, 128.6, 128.5, 126.2, 121.3, 67.4

13C

(d), 61.6, 19.4 (d) and -1.7. 31P NMR (121 MHz, CDCl ) β5.1. 3 With dimethylsulfide, nitrogen in ethanol, dichloromethane Patent; King, Ivan C.; Doyle, Terrance W.; Sznol, Mario; Sartorelli, Alan C.; Cheng, Yung-Chi; US2002/188011; (2002); (A1) English View in Reaxys

O N

N O

Rx-ID: 4857648 View in Reaxys 62/115 Yield

Conditions & References

86 %

With ammonium nitrate, Montmorillonite-K10, Time= 0.05h, microwave irradiation, deprotection Meshram; Sumithra; Reddy; Ganesh; Yadav; Synthetic Communications; vol. 29; nb. 16; (1999); p. 2807 - 2815 View in Reaxys

76 %

With lithium chloride in water, dimethyl sulfoxide, Time= 18h, T= 130 °C Mandal, Pijus Kumar; Dutta, Pinak; Roy, Subhas Chandra; Tetrahedron Letters; vol. 38; nb. 41; (1997); p. 7271 - 7274 View in Reaxys

Rx-ID: 5190415 View in Reaxys 63/115 Yield 55 %

Conditions & References With triphenylporphine, oxygen in benzene, Time= 5h, Irradiation, Oxidation Bonesi, Sergio M.; Torriani, Rosangela; Mella, Mariella; Albini, Angelo; European Journal of Organic Chemistry; nb. 7; (1999); p. 1723 - 1728

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View in Reaxys

S O

Rx-ID: 5190416 View in Reaxys 64/115 Yield

Conditions & References

3 %, 74 %

With oxygen, rose bengal in methanol, Time= 0.166667h, Irradiation, Oxidation Bonesi, Sergio M.; Torriani, Rosangela; Mella, Mariella; Albini, Angelo; European Journal of Organic Chemistry; nb. 7; (1999); p. 1723 - 1728 View in Reaxys

N OH

Cl Cu

(v1)

H N

O O

O N H

Rx-ID: 24276473 View in Reaxys 65/115 Yield

Conditions & References 12 : EXAMPLE 12 EXAMPLE 12 This Example illustrates the preparation of 2-pyridinecarboxaldehyde. Copper (I) chloride (12.5 mg) and 1,10-phenanthroline (24 mg) were added to toluene (12 ml) with stirring. Potassium carbonate (0.7 g), 1,2-dicarbethoxyhydrazine (0.11 g) and pyridine-2-methanol (0.27 g) were then added to the reaction mixture. Oxygen was bubbled into the mixture and the mixture was stirred at 80° C. for 4 hours. 1 H NMR analysis of the reaction mixture showed a 94percent conversion to the title compound. With potassium carbonate in toluene Patent; Zeneca Limited; US5912388; (1999); (A) English View in Reaxys

N O N

NH 2

Rx-ID: 25360483 View in Reaxys 66/115 Yield

Conditions & References

79 mg (85%)

Reductive Amination Of An Aldehyde And A Primary Amine: 2-pyridine carboxaldehyde (35 mg, 0.33 mmol) and 4-amino-l-benzylpiperidine (93 mg, 0.5 mmol) yielded 79 mg (85percent) MS (m/e): 282 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

N O H 2N

Rx-ID: 25360484 View in Reaxys 67/115 Yield 52 mg (74%)

Conditions & References Reductive Amination Of An Aldehyde And A Primary Amine: 2-pyridine carboxaldehyde (35 mg, 0.33 mmol) and β-methyl benzylamine (60 mg, 0.5 mmol) yielded 52 mg (74percent) MS (m/e): 213 (M+1)

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Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

O NH 2

Rx-ID: 25360485 View in Reaxys 68/115 Yield

Conditions & References

24 mg (37%)

Reductive Amination Of An Aldehyde And A Primary Amine: 2-pyridine carboxaldehyde (35 mg, 0.33 mmol) and tetrahydrofurfurylamine (51 mg, 0.5 mmol) yielded 24 mg (37percent) MS (m/e): 193 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

H 2N

Rx-ID: 25360486 View in Reaxys 69/115 Yield

Conditions & References

90 mg (81%)

Reductive Amination Of An Aldehyde And A Primary Amine: 2-pyridine carboxaldehyde (35 mg, 0.33 mmol) and 2-[(2-aminomethyl)phenylthio]benzyl alcohol (122 mg, 0.5 mmol) yielded 90 mg (81percent) MS (m/e): 337 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

N O

NH 2

Rx-ID: 25360487 View in Reaxys 70/115 Yield 74 mg (90%)

Conditions & References Reductive Amination Of An Aldehyde And A Primary Amine: 2-pyridine carboxaldehyde (35 mg, 0.33 mmol) and tryptamine (122 mg, 0.5 mmol) yielded 74 mg (90percent) MS (m/e): 252 (M+1) Patent; ELI LILLY AND COMPANY; EP818431; (1998); (A1) English View in Reaxys

N O N

Rx-ID: 4813812 View in Reaxys 71/115 Yield 40 %

Conditions & References With n-butyllithium, 2-(N,N-dimethylamino)athanol, 1.) hexane, -78 deg C, 1 h, 2.) THF, -40 deg C, 30 min Gros, Philippe; Fort, Yves; Caubere, Paul; Journal of the Chemical Society - Perkin Transactions 1; nb. 24; (1997); p. 3597 3600 View in Reaxys

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O N

Rx-ID: 4353489 View in Reaxys 72/115 Yield

Conditions & References

61 %

With aluminium trichloride in dichloromethane, Time= 4h, T= -78 °C Niestroj, Michael; Neumann, Wilhelm P.; Chemische Berichte; vol. 129; nb. 1; (1996); p. 45 - 51 View in Reaxys O

Rx-ID: 4461588 View in Reaxys 73/115 Yield

Conditions & References With 3 A molecular sieve, zirconium(IV) tert-butoxide in dichloromethane, Time= 26h, T= 60 °C Krohn, Karsten; Vinke, Ingeborg; Adam, Horst; Journal of Organic Chemistry; vol. 61; nb. 4; (1996); p. 1467 - 1472 View in Reaxys O

Rx-ID: 4461589 View in Reaxys 74/115 Yield

Conditions & References With tert.-butylhydroperoxide, 3 A molecular sieve, zirconium(IV) tert-butoxide in dichloromethane, Time= 26h, T= 60 °C Krohn, Karsten; Vinke, Ingeborg; Adam, Horst; Journal of Organic Chemistry; vol. 61; nb. 4; (1996); p. 1467 - 1472 View in Reaxys

N O N

Rx-ID: 3943100 View in Reaxys 75/115 Yield

Conditions & References With n-butyllithium, Multistep reaction Uenishi, Jun'ichi; Nishiwaki, Kenji; Hata, Shinichiro; Nakamura, Kaoru; Tetrahedron Letters; vol. 35; nb. 43; (1994); p. 7973 - 7976 View in Reaxys O

N O

Rx-ID: 4185870 View in Reaxys 76/115 Yield 84 %

Conditions & References With 1,4-diaza-bicyclo[2.2.2]octane in ethanol, Time= 3h, Ambient temperature Kinoshita; Ohishi; Journal of Heterocyclic Chemistry; vol. 31; nb. 6; (1994); p. 1599 - 1603 View in Reaxys

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O N

N O

Rx-ID: 4185871 View in Reaxys 77/115 Yield

Conditions & References With sodium methylate in methanol, Time= 3h, Ambient temperature, Yield given. Yields of byproduct given. Title compound not separated from byproducts Kinoshita; Ohishi; Journal of Heterocyclic Chemistry; vol. 31; nb. 6; (1994); p. 1599 - 1603 View in Reaxys NH 2 N

Rx-ID: 1574046 View in Reaxys 78/115 Yield

Conditions & References

24 %, 62 %

With samarium diiodide in tetrahydrofuran, Time= 0.583333h, Ambient temperature Kamochi; Kudo; Tetrahedron; vol. 48; nb. 21; (1992); p. 4301 - 4312 View in Reaxys

N H

Rx-ID: 1646689 View in Reaxys 79/115 Yield

Conditions & References With (batho)2CuII (batho = 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrolinedisulfonate), water in methanol, Time= 24h, T= 25 °C , pH 8, Rate constant Wang, Fengjiang; Sayre, Lawrence M.; Journal of the American Chemical Society; vol. 114; nb. 1; (1992); p. 248 - 255 View in Reaxys OH

Rx-ID: 1794632 View in Reaxys 80/115 Yield

Conditions & References Equilibrium constant Owen, Terence C.; Journal of Heterocyclic Chemistry; vol. 27; nb. 4; (1990); p. 987 - 990 View in Reaxys O–

N OH

Rx-ID: 2323147 View in Reaxys 81/115 Yield

Conditions & References Equilibrium constant Owen, Terence C.; Journal of Heterocyclic Chemistry; vol. 27; nb. 4; (1990); p. 987 - 990 View in Reaxys

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OH H +

Rx-ID: 2448407 View in Reaxys 82/115 Yield

Conditions & References Equilibrium constant Owen, Terence C.; Journal of Heterocyclic Chemistry; vol. 27; nb. 4; (1990); p. 987 - 990 View in Reaxys

Rx-ID: 2454817 View in Reaxys 83/115 Yield

Conditions & References in benzene-d6, Equilibrium constant Katritzky, Alan R.; Perumal, Subbu; Savage, G. Paul; Journal of the Chemical Society, Perkin Transactions 2; nb. 6; (1990); p. 921 - 924 View in Reaxys

N N

Rx-ID: 2454830 View in Reaxys 84/115 Yield

N O

O N O

Rx-ID: 2554050 View in Reaxys 85/115 Yield 17 %

Conditions & References With tin(IV) chloride in 1,2-dichloro-ethane, Time= 0.25h, T= 0 °C Raja, S.; Xavier, N.; Arulraj, S. J.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 28; nb. 1-11; (1989); p. 687 - 689 View in Reaxys With boron trifluoride diethyl etherate in 1,2-dichloro-ethane, Time= 0.25h, T= 0 °C , Yield given Raja, S.; Xavier, N.; Arulraj, S. J.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 28; nb. 1-11; (1989); p. 687 - 689 View in Reaxys

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O O

H N N

N N

N O

N N

O O

Rx-ID: 3163867 View in Reaxys 86/115 Yield 8 %, 88 %

Conditions & References With sodium methylate in ethanol, Time= 3h, Heating, Product distribution Neunhoeffer, Hans; Diehl, Werner; Karafiat, Ute; Liebigs Annalen der Chemie; (1989); p. 105 - 110 View in Reaxys O N

N O OH N

O N

Rx-ID: 1518289 View in Reaxys 87/115 Yield

Conditions & References

42 %, 20 %, Time= 14h, T= 140 °C , Product distribution 5 %, 20 %, Bruni, Paolo; Conti, Carla; Tosi, Giorgio; Monatshefte fuer Chemie; vol. 119; (1988); p. 1311 - 1316 50 % View in Reaxys O N

N O OH N N

N O

N HO

Rx-ID: 1518290 View in Reaxys 88/115 Yield

Conditions & References

42 %, 20 %, Time= 14h, T= 140 °C , Further byproducts given 20 %, 50 % Bruni, Paolo; Conti, Carla; Tosi, Giorgio; Monatshefte fuer Chemie; vol. 119; (1988); p. 1311 - 1316 View in Reaxys

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N O

H H

H H O

racemate

Rx-ID: 1568659 View in Reaxys 89/115 Yield

Conditions & References in acetonitrile, Time= 6h, Heating Grigg, Ronald; Idle, Jonathan; McMeekin, Peter; Surendrakumar, Sivagnanasundram; Vipond, David; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 2703 - 2714 View in Reaxys

N O

Rx-ID: 2554051 View in Reaxys 90/115 Yield

Conditions & References With aluminum oxide, T= 200 °C , other temperatures, other catalyst, Product distribution Raja, S.; Xavier, N.; Arulraj, S. J.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 27; nb. 1-12; (1988); p. 916 - 919 View in Reaxys O

N N

N O

Rx-ID: 3829252 View in Reaxys 91/115 Yield

Conditions & References

42 %, 20 %, With .alpha.-picoline, Time= 14h, T= 140 °C , Further byproducts given 20 %, 50 % Bruni, Paolo; Conti, Carla; Tosi, Giorgio; Monatshefte fuer Chemie; vol. 119; (1988); p. 1311 - 1316 View in Reaxys

N H N

(v4)

O Co 3+

N H (v4)

(v4)

H N

(v6)

(v3)

N O

Co (v6)

O H

(v4)

N H (v4)

(v4)

Rx-ID: 26476249 View in Reaxys 92/115 Yield

Conditions & References With oxygen in not given, Kinetics, byproducts: Co(II), H2O; oxidative dehydrogenation at 50.0°C at pH 11.88 (mechanism proposed); prod. detn. as (2,4-dinitrophenyl)hydrazone Basak, Arup K.; Martell, Arthur E.; Inorganic Chemistry; vol. 27; (1988); p. 1948 - 1955 ; (from Gmelin) View in Reaxys

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N O

carbon oxides Rx-ID: 5727606 View in Reaxys 93/115 Yield

Conditions & References With β-VO(PO3)2 in gas, T= 400 °C , selectivity of reaction, rates of partial and total oxidation, Product distribution, Rate constant Leitis, L. Ya.; Skolmeistere, R. A.; Golender, L. O.; Yansone, D. P.; Meksh, P. A.; Shimanskaya, M. V.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 1; (1986); p. 63 - 66; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 1; (1986); p. 75 - 79 View in Reaxys

O N

Rx-ID: 2155161 View in Reaxys 94/115 Yield

Conditions & References

92 %

With selenium(IV) oxide in chlorobenzene, Time= 6h, T= 132 °C Jones, Gurnos; Mouat, Deborah J.; Tonkinson, Daryl J.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1985); p. 2719 - 2724 View in Reaxys

N O O (v1) OHO N(v4)CoN (v4) (v4)N (v4)N (v6) O HO (v4)(v1) N

Rx-ID: 26852613 View in Reaxys 95/115 Yield

Conditions & References

14 %, 86 %

in methanol, decomposition of the complex by refluxing in methanol under N2 for 6-8 h; evapn. of the solvent, extn. of the organic compounds with ether, gas chromatography Gupta, B. D.; Roy, Sujit; Inorganica Chimica Acta; vol. 108; (1985); p. 261 - 264 ; (from Gmelin) View in Reaxys

N O (v1)O OHO N(v4)CoN (v4) (v4)N (v4)N (v6) O HO (v4)(v1) N

N O

Rx-ID: 26852614 View in Reaxys 96/115 Yield

Conditions & References in benzene, decomposition of the complex by refluxing in benzene under N2 for 6-8 h; evapn. of the solvent, extn. of the organic compound with ether, gas chromatography Gupta, B. D.; Roy, Sujit; Inorganica Chimica Acta; vol. 108; (1985); p. 261 - 264 ; (from Gmelin) View in Reaxys

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O N N H

NH 2

Rx-ID: 1660162 View in Reaxys 97/115 Yield

Conditions & References With n-butyllithium in tetrahydrofuran, hexane, Time= 2h, T= -78 °C , Yield given Barton, Derek H. R.; Lukacs, Gabor; Wagle, Dilip; Journal of the Chemical Society, Chemical Communications; nb. 8; (1982); p. 450 - 452 View in Reaxys

Cl Cl

Rx-ID: 2324406 View in Reaxys 98/115 Yield

Conditions & References

82 % Chromat.

With 4-(dimethylamino)pyridine N-oxide in acetonitrile, Time= 3h, Heating Mukaiyama, Shigemi; Inanaga, Junji; Yamaguchi, Masaru; Bulletin of the Chemical Society of Japan; vol. 54; nb. 7; (1981); p. 2221 - 2222 View in Reaxys

N O

Rx-ID: 1518306 View in Reaxys 99/115 Yield

Conditions & References

25.7 % Chromat., 5.5 % Chromat., 1.6 % Chromat.

With air, water, vanadia, Time= 0.000833333h, T= 320 °C , oth. time, oth. temperature, oth. ratio of reactants, Product distribution Suvorov, B. V.; Glubokovskikh, L. K.; Kan, I. I.; J. Appl. Chem. USSR (Engl. Transl.); vol. 53; nb. 11; (1980); p. 2519 2521,1866 - 1867 View in Reaxys

Rx-ID: 81623 View in Reaxys 100/115 Yield

Conditions & References With 1,4-dioxane, selenium(IV) oxide, T= 90 - 100 °C Furukawa; Yakugaku Zasshi; vol. 78; (1958); p. 957,959; ; (1959); p. 3219 View in Reaxys O–

N OH Cu 2+

Rx-ID: 540982 View in Reaxys 101/115 Yield

Conditions & References T= 120 °C , p= 0.01Torr Hemmerich; Fallab; Helvetica Chimica Acta; vol. 41; (1958); p. 498,509 View in Reaxys

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O 2

C– N

Cu 2+

N O

(v4) (v3)

Rx-ID: 26731521 View in Reaxys 102/115 Yield

Conditions & References in neat (no solvent), at 100°C and 0.01 Torr; Hemmerich, P.; Fallab, S.; Helvetica Chimica Acta; vol. 41; (1958); p. 498 - 513 ; (from Gmelin) View in Reaxys in not given, solving of Cu(C6H4NO)2*2H2O in dild. acid; Hemmerich, P.; Fallab, S.; Helvetica Chimica Acta; vol. 41; (1958); p. 498 - 513 ; (from Gmelin) View in Reaxys in neat (no solvent), at 100°C and 0.01 Torr; vol. Cu: MVol.B4; 114, page 1690 - 1693 ; (from Gmelin) View in Reaxys in not given, solving of Cu(C6H4NO)2*2H2O in dild. acid; vol. Cu: MVol.B4; 114, page 1690 - 1693 ; (from Gmelin) View in Reaxys

N O N O

Rx-ID: 22000 View in Reaxys 103/115 Yield

Conditions & References With trichlorophosphate Mingoia; Ferreira; ; vol. 11; (1953); p. 9,13 View in Reaxys

O N O

Rx-ID: 768888 View in Reaxys 104/115 Yield

Conditions & References With hydrogenchloride, water, unter Stickstoff Wibaut; Huls; Recueil des Travaux Chimiques des Pays-Bas; vol. 71; (1952); p. 1021,1025 View in Reaxys

N O

Rx-ID: 806898 View in Reaxys 105/115 Yield

Conditions & References With ozone, ethyl acetate, T= -20 - -15 °C , und Zersetzen des Ozonids mit wasser,Zink-Pulver und wss.Silbernitrat-Loesung in Gegenwart von Hydrochinon Hart; Journal of the Chemical Society; (1952); p. 4540 View in Reaxys

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Br N

N O

Rx-ID: 22199296 View in Reaxys 106/115 Yield

Conditions & References Reaction Steps: 2 1: benzene 2: water; hydrochloric acid / unter Stickstoff With hydrogenchloride, water, benzene Wibaut; Huls; Recueil des Travaux Chimiques des Pays-Bas; vol. 71; (1952); p. 1021,1025 View in Reaxys

air

steam

molybdenum (VI)-oxide

N O

vanadium(V)-oxide Rx-ID: 5406797 View in Reaxys 107/115 Yield

Conditions & References T= 400 °C Mathes et al.; Chemische Berichte; vol. 84; (1951); p. 452,456 View in Reaxys

N O

N N OH

Rx-ID: 22288992 View in Reaxys 108/115 Yield

Conditions & References Reaction Steps: 2 1: palladium/ asbestos; ethanolic HCl / Hydrogenation 2: lead (IV)-acetate; benzene With lead(IV) acetate, hydrogenchloride, magnesium hydrosilicate, palladium, benzene Mathes et al.; Chemische Berichte; vol. 84; (1951); p. 452,456 View in Reaxys Cl N

N Cl

Rx-ID: 74179 View in Reaxys 109/115 Yield

Conditions & References With sulfuric acid, water Dyson; Hammick; Journal of the Chemical Society; (1939); p. 781 View in Reaxys With ethanol, water, silver nitrate Dyson; Hammick; Journal of the Chemical Society; (1939); p. 781 View in Reaxys

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Rx-ID: 22211269 View in Reaxys 110/115 Yield

Conditions & References Reaction Steps: 2 1: tin (II)-chloride; concentrated aqueous hydrochloric acid; acetone 2: silver nitrate; water; ethanol With hydrogenchloride, ethanol, water, silver nitrate, acetone, tin(ll) chloride Dyson; Hammick; Journal of the Chemical Society; (1939); p. 781 View in Reaxys

NH 2

O N O

Rx-ID: 45855 View in Reaxys 111/115 Yield

Conditions & References Graf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 146; (1936); p. 88,102 View in Reaxys

H N

N O

Rx-ID: 46051 View in Reaxys 112/115 Yield

Conditions & References With thionyl chloride, diethyl ether Graf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 146; (1936); p. 88,102 View in Reaxys With ethanol, Nitrosobenzene Graf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 146; (1936); p. 88,102 View in Reaxys

N NH 2

S O

Rx-ID: 5406795 View in Reaxys 113/115 Yield

Conditions & References Graf; Journal fuer Praktische Chemie (Leipzig); vol. <2> 146; (1936); p. 88,102 View in Reaxys

N N

Rx-ID: 806907 View in Reaxys 114/115 Yield

Conditions & References With hydrogenchloride, ozone Harries; Lenart; Justus Liebigs Annalen der Chemie; vol. 410; (1915); p. 111 View in Reaxys Lenart; Chemische Berichte; vol. 47; (1914); p. 808 View in Reaxys

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N O

phenylhydrazone of 2-formyl-pyridine Rx-ID: 5406796 View in Reaxys 115/115 Yield

Conditions & References With hydrogenchloride, Faellen des entstandenen Phenylhydrazins mit 2.4-Dinitro-benzaldehyd Kaufmann; Vallette; Chemische Berichte; vol. 46; (1913); p. 54; Chemische Berichte; vol. 45; (1912); p. 1742 View in Reaxys

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