3-Methoxybenzonitrile [C8H7NO] by Asch

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Date

96 reactions in Reaxys

2018-05-30 15h:39m:08s (UTC)

N O

1. Query

Search as: Product, As drawn, No mixtures ))

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NH 2

Rx-ID: 4153802 View in Reaxys 1/96 Yield 91 %

Conditions & References Typical experimental procedure for aerobic oxidation of amine General procedure: A double necked round bottomed flask (10 ml), equipped with magnetic stirrer was charged with amine (1 mmol) and catalyst 3 (5 wt percent) and the resulting mixture was heated at 100 °C for 0.5 h under constant purging of molecular oxygen. After completion of the reaction, the mixture was diluted with ethyl acetate and the recovered catalyst was separated by decantation. The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was further purified by column chromatography over silica gel using a solvent system of hexane and ethyl acetate (4:1) as eluent. With C22H22Cl2FeN2O8 (2-)*2C16H36N(1+), oxygen in neat (no solvent), Time= 0.5h, T= 100 °C , p= 760.051Torr , Green chemistry Varyani, Manish; Khatri, Praveen K.; Jain, Suman L.; Tetrahedron Letters; vol. 57; nb. 7; (2016); p. 723 - 727 View in Reaxys

90 %

With potassium hydroxide, nickel copper formate, (Bu4N)2S2O8 in dichloromethane, Time= 10h, T= 20 °C , Oxidation Chen, Fen-Er; Peng, Zuo-Zhong; Fu, Han; Liu, Ji-Dong; Shao, Lan-Ying; Journal of Chemical Research - Part S; nb. 12; (1999); p. 726 - 727 View in Reaxys

87 %

With pyridine, 4-(acetylamino)-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate in dichloromethane, Time= 12h, T= 20 °C , Inert atmosphere Lambert, Kyle M.; Bobbitt, James M.; Eldirany, Sherif A.; Wiberg, Kenneth B.; Bailey, William F.; Organic Letters; vol. 16; nb. 24; (2014); p. 6484 - 6487 View in Reaxys

84 %

With dmap, copper(l) iodide, 9-azabicyclo[3.3.1]nonane N-oxyl, oxygen, 4,4'-di-tert-butyl-2,2'- bipyridine in acetonitrile, Time= 15h, T= 20 °C , p= 760.051Torr , Reagent/catalyst Kim, Jinho; Stahl, Shannon S.; ACS Catalysis; vol. 3; nb. 7; (2013); p. 1652 - 1656 View in Reaxys

97 % Chromat.

With iodine, tert-butylamine in acetonitrile, Time= 6h, Ambient temperature Goosen, Andre; McCleland, Cedric W.; Sipamia, Allworth M.; Journal of Chemical Research, Miniprint; nb. 1; (1995); p. 311 - 332 View in Reaxys With oxygen, aluminum oxide, ruthenium in various solvent(s), Time= 1h, T= 99.85 °C , p= 760Torr Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 42; nb. 13; (2003); p. 1480 - 1483 View in Reaxys With oxygen, aluminum oxide, ruthenium in various solvent(s), Time= 1h, T= 99.84 °C , p= 760.051Torr Yamaguchi, Kazuya; Mizuno, Noritaka; Chemistry - A European Journal; vol. 9; nb. 18; (2003); p. 4353 - 4361 View in Reaxys

90 % Chromat.

With oxygen, RuHAP in toluene, Time= 12h, T= 110 °C Mori; Yamaguchi; Mizugaki; Ebitani; Kaneda; Chemical Communications; nb. 5; (2001); p. 461 - 462 View in Reaxys

80 %Chromat.

With oxygen in toluene, Time= 16h, T= 85 °C , p= 760.051Torr Karimi, Babak; Yari, Omolbanin; Khorasani, Mojtaba; Vali, Hojatollah; Mansouri, Fariborz; ChemCatChem; vol. 10; nb. 8; (2018); p. 1783 - 1787

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View in Reaxys 4

K+ -4 N

N (v6)

N N N

Rx-ID: 47062039 View in Reaxys 2/96 Yield

Conditions & References

81 %Chromat.

With tetra(adamantyl)biphosphine, palladium diacetate, sodium carbonate in 1-methyl-pyrrolidin-2-one, Time= 16h, T= 140 °C , Inert atmosphere Zhang, Shaoke; Neumann, Helfried; Beller, Matthias; Chemistry - A European Journal; vol. 24; nb. 1; (2018); p. 67 - 70 View in Reaxys N

O O

Rx-ID: 3389612 View in Reaxys 3/96 Yield 98 %

Conditions & References With oxygen, copper, ammonium chloride in pyridine, Time= 24h, T= 60 °C Capdevielle, Patrice; Lavigne, Andre; Maumy, Michel; Synthesis; nb. 6; (1989); p. 451 - 452 View in Reaxys

97 %

General procedure forthe synthesis of nitrile from aldehyde General procedure: Aldehyde(1 mmol) and hydroxylamine hydrochloride (1.2 mmol) were added successively toa solution of anhydrous ferric chloride (0.5 mmol) in 5 ml dry DMF. The mixturewas reflux for appropriate time (Table 2). The progress of the reaction wasmonitored by TLC. After completion of the reaction, the solution was pouredinto 100 ml water and extract with ethyl acetate washed several times withwater. The combined organic mixture was dried over anhydrous Na2SO4,concentrated and the residue was purified by column chromatography on silicagel 60-120 mesh using petroleum ether/ethyl acetate (96:4) as eluent to affordthe pure nitrile. All the products were characterized by IR, 1H NMRand 13C NMR. With iron(III) chloride, hydroxylamine hydrochloride in N,N-dimethyl-formamide, Time= 4h, Reflux Ghosh, Pranab; Subba, Raju; Tetrahedron Letters; vol. 54; nb. 36; (2013); p. 4885 - 4887 View in Reaxys

96 %

With ammonium iodide in dimethyl sulfoxide, Time= 4h, T= 20 °C , Electrolysis Qu, Qinghui; Gao, Xiaofang; Gao, Jian; Yuan, Gaoqing; Science China Chemistry; vol. 58; nb. 4; (2015); p. 747 - 750 View in Reaxys

94 %

With hydroxylamine hydrochloride, tetrachlorosilane, Time= 0.0166667h, T= 105 °C , microwave irradiation Srinivas; Mahender; Das, Biswanath; Chemistry Letters; vol. 32; nb. 8; (2003); p. 738 - 739 View in Reaxys

94 %

13 A typical method for preparation of nitrile from aldehyde using AHA: General procedure: 4-Isopropylbenzaldehyde 1a (0.50 g, 3.37 mmol), acetohydroxamic acid (0.30 g, 4.05 mmol), acetonitrile (5 ml), and Bi(OTf)3 (0.11 g, 0.17 mmol) were taken into a 25 ml round-bottomed flask fitted with a condenser and calcium chloride guard tube. The mixture was refluxed for 14 h and after completion of the reaction (GC, 10percent SE-30 on Chromosorb, 10' .x. 1/8 column), the reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product obtained was purified by normal column chromatography(silica gel 100-200 mesh, ethyl acetate/hexane = 1:20) to obtain 4-isopropylbenzonitrile 3a (0.47 g, 97percent). With bismuth(lll) trifluoromethanesulfonate, acetylhydroxamic acid in acetonitrile, Time= 16h, Reflux

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Sridhar, Madabhushi; Reddy, Mallu Kishore Kumar; Sairam, Vangipuram Venkata; Raveendra, Jillella; Godala, Kondal Reddy; Narsaiah, Chinthala; Ramanaiah, Beeram China; Reddy, Cirandur Suresh; Tetrahedron Letters; vol. 53; nb. 27; (2012); p. 3421 - 3424 View in Reaxys 94 %

With trifluorormethanesulfonic acid, O-benzenesulfonyl-acetohydroxamic acid ethyl ester in dichloromethane, Time= 24h, T= 23 °C , Inert atmosphere Hyodo, Kengo; Togashi, Kosuke; Oishi, Naoki; Hasegawa, Genna; Uchida, Kingo; Organic Letters; vol. 19; nb. 11; (2017); p. 3005 - 3008 View in Reaxys

93 %

General procedure for the synthesis of nitriles from aldehydes General procedure: Aldehyde (0.5 mmol) and hydroxylamine hydrochloride (0.75 mmol) were added successively to a solution of Fe3O4-CTAB NPs (5.7 mg) i.e Fe3O4 (1.8 molpercent) in 5 ml dry DMF. The mixture was refluxed for appropriate time (table 3). The progress of the reaction was monitored by TLC. After completion of the reaction, the solution was poured into 100 ml water and extract with ethyl acetate, washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography on silica gel 60-120 mesh using petroleum ether/ ethyl acetate (95:5) as eluent to afford the pure nitrile. All the products were characterized by IR, 1H NMR and 13C NMR. With hydroxylamine hydrochloride in N,N-dimethyl-formamide, Time= 1h, Reflux Ghosh, Pranab; Saha, Bittu; Pariyar, Gyan Chandra; Tamang, Abiral; Subba, Raju; Tetrahedron Letters; vol. 57; nb. 32; (2016); p. 3618 - 3621 View in Reaxys

92 %

With hydroxylamine hydrochloride, ammonium acetate, Time= 0.0333333h, microwave irradiation, Condensation, Dehydration Das; Ramesh; Madhusudhan; Synlett; nb. 11; (2000); p. 1599 - 1600 View in Reaxys

92 %

With XY-zeolite, hydroxylamine hydrochloride, Time= 0.0166667h, microwave irradiation Srinivas; Reddy, E. Bolla; Das, Biswanath; Synlett; nb. 4; (2002); p. 625 - 627 View in Reaxys

92 %

Typical Procedure for Preparation of 4-Methoxybenzonitrile General procedure: To a solution of 4-methoxybenzaldehyde (1mmol, 0.136 g) in dry DMF (5mL), hydroxylamine hydrochloride (3 mmol, 0.208 g) was added with stirring for 15 min at 120 °C. HAP(at)AEPH2-SO3H nanocatalyst (8 mol-percent, 0.08 g) was then added to the resultant solution. After completion of the reaction (which was monitored byTLC), cooling, and separation of the nanocatalyst by centrifugation, the reaction mixture was poured into water (10mL). The resulting mixture was extracted with ethyl acetate (310mL) and dried over sodium sulfate. After evaporation of the solvent, the crude product was purified by thin-layer chromatography using n-hexane/ethyl acetate (4 : 1) as eluent to afford 4-methoxybenzonitrile (0.130 g, 98percent). With hydroxylamine hydrochloride in N,N-dimethyl-formamide, Time= 1.5h, T= 120 °C , Green chemistry Masjed, Samane Memar; Akhlaghinia, Batool; Zarghani, Monireh; Razavi, Nasrin; Australian Journal of Chemistry; vol. 70; nb. 1; (2017); p. 33 - 43 View in Reaxys

91 %

With PhNHCO2NH2*TsOH in toluene, Time= 0.5h, Heating, Condensation, elimination Coskun, Necdet; Arikan, Nevin; Tetrahedron; vol. 55; nb. 40; (1999); p. 11943 - 11948 View in Reaxys

91 %

With manganese(IV) oxide, ammonia, magnesium sulfate in tetrahydrofuran, isopropyl alcohol, Time= 17h, T= 20 °C Lai; Bhamare; Anderson; Synlett; nb. 2; (2001); p. 230 - 231 View in Reaxys

90 %

With potassium hydroxide, ammonium bicarbonate, (Bu4N)2S2O8, copper(I) formate, nikel(II) formate in acetonitrile, Time= 1.5h, T= 20 °C , Condensation, Oxidation Chen; Fu; Meng; Cheng; Lu; Synthesis; nb. 11; (2000); p. 1519 - 1520 View in Reaxys

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74 %

With trimethylsilylazide, zirconium(IV) chloride in acetonitrile, Time= 0.333333h, T= 20 °C Nimnual, Phongprapan; Tummatorn, Jumreang; Thongsornkleeb, Charnsak; Ruchirawat, Somsak; Journal of Organic Chemistry; vol. 80; nb. 17; (2015); p. 8657 - 8667 View in Reaxys

72 %

With O-(4-(trifluoromethyl)benzoyl)hydroxylamine, trifluoroacetic acid in 1,2-dimethoxyethane, Time= 60h, T= 80 °C An, Xiao-De; Yu, Shouyun; Organic Letters; vol. 17; nb. 20; (2015); p. 5064 - 5067 View in Reaxys Reaction Steps: 2 1: hydroxylamine hydrochloride 2: 44 percent Chromat. / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetonitrile / 0.5 h / Photolysis With hydroxylamine hydrochloride, 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile De Lijser, H.J. Peter; Hsu, Susan; Marquez, Bernadette V.; Park, Adriana; Sanguantrakun, Nawaporn; Sawyer, Jody R.; Journal of Organic Chemistry; vol. 71; nb. 20; (2006); p. 7785 - 7792 View in Reaxys Reaction Steps: 2 1: hydroxylamine sulphate; sodium acetate / ethanol 2: SOCl2 / benzene / Heating With thionyl chloride, sodium acetate, hydroxylamine sulfate in ethanol, benzene Master, Hoshang E.; Khan, Shabana I.; Poojari, Krishna A.; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 7; (2003); p. 1249 - 1251 View in Reaxys With ammonia, iodine in tetrahydrofuran, water, T= 20 °C Jadhav, Ganesh R.; Shaikh, Mohammad U.; Kale, Rajesh P.; Ghawalkar, Anand R.; Gill, Charansingh H.; Journal of Heterocyclic Chemistry; vol. 46; nb. 5; (2009); p. 980 - 987 View in Reaxys With ammonia, iodine in tetrahydrofuran, water, Time= 1h, T= 20 °C Reddy, M.B.Madhusudana; Pasha; Synthetic Communications; vol. 41; nb. 14; (2011); p. 2081 - 2085 View in Reaxys Reaction Steps: 2 1: pyridine / dichloromethane / 0.08 h / 20 °C 2: 4-(acetylamino)-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate / dichloromethane / 12 h / 20 °C With pyridine, 4-(acetylamino)-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate in dichloromethane Kelly, Christopher B.; Lambert, Kyle M.; Mercadante, Michael A.; Ovian, John M.; Bailey, William F.; Leadbeater, Nicholas E.; Angewandte Chemie - International Edition; vol. 54; nb. 14; (2015); p. 4241 - 4245 View in Reaxys General procedure for preparation of compounds a1–a17 General procedure: A mixture of aromatic aldehydes (50mmol) (1–17), hydroxylamine hydrochloride (62.5mmol), sodium acetate (125mmol) were dissolved in the mixture of formic acid and water (60:40) and stirred at 80°C until TLC analysis indicated the disappearance of aromatic aldehydes. Then, cooling the reaction system to room temperature and put it into water to obtain the target compounds. Some desired products which were dissolved in the mixture of water and formic acid can be obtained by salting out. Then, solid target compounds were obtained by filtration and recrystallized by alcohol, and then dried under vacuum. While, some target compounds are oily. These oily compounds were obtained by extraction with ethyl acetate and the solvent was removed at the vacuum to afford aryl nitriles (a1–a17). With formic acid, hydroxylamine hydrochloride, sodium acetate in water, T= 80 °C Lin, Hong-Yan; Li, Zi-Kang; Bai, Li-Fei; Baloch, Shahla Karim; Wang, Fang; Qiu, Han-Yue; Wang, Xue; Qi, Jin-Liang; Yang, Raong-Wu; Wang, Xiao-Ming; Yang, Yong-Hua; Biochemical Pharmacology; vol. 96; nb. 2; (2015); p. 93 - 106 View in Reaxys

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N O

Rx-ID: 7174474 View in Reaxys 4/96 Yield

Conditions & References

99 %

4 : Synthesis of 2-naphthonitrile (compound 3a) using ethyl O-benzenesulfonyl-acetohydroxamate (compound 2a) General procedure: At room temperature, under an argon atmosphere,2-naphthaldehyde (53.2 mg, 0.340 mmol, 1.0 eq.) As an aldehyde compound and a perchloric acid aqueous solution (70 wtpercent, 1.5 μL, 0.0170 mmol, 5 mol Methylene chloride (0.68 mL, 0.50 M), ethyl O-benzenesulfonyl-acetohydroxamate (86.9 mg, 0.357 mmol, 1.05 eq.) Was added and the mixture was stirred at room temperature for 24 hours.Thereafter, 20 ml of methylene chloride was added, the reaction solution was filtered through a pad of silica gel under reduced pressure, and the solvent was distilled off to measure the NMR. Silica gel column chromatography (Kanto Chemical silica gel 60 (40 - 50 μm),Hexane / diethyl ether = 9/1) to obtain 52.0 mg (yield 99percent) of white 2-naphthonitrile (Compound 3a). With perchloric acid, O-benzenesulfonyl-acetohydroxamic acid ethyl ester in dichloromethane, Time= 24h, T= 20 °C , Inert atmosphere Patent; RYUKOKU UNIVERSITY; HYODO, KENGO; OISHI, NAOKI; TOGASHI, KOSUKE; (10 pag.); JP2017/149687; (2017); (A) Japanese View in Reaxys

93.4%

1.a : (a) (a) 3-METHOXY BENZONITRILE 3-bromoanysole (210 mg, 1.12 mmoles) and CuCN (93.14 mg, 1.04 mmoles) were dissolved in N-methyl pyrrolidone (mL) and the reaction mixture is warmed to 220° C. for 2 hours. After cooling to 50° C., the reaction mixture was added both 6 mL of an aqueous solution containing 400 mg of FeCl3.6H2O and 0.6 mL 37percent HCl, then was maintained under stirring at 65° C. for 20 min. After addition of 20 mL water the raw product was extracted by ethyl ether (5*20 mL); the organic phase de-hydrated by Na2SO4, was dried giving 114.3 mg of the crude compound (93.4percent) Patent; Geange Ltd.; US6323230; (2001); (B1) English View in Reaxys Hettler,H.; Neygenfind,H.; Chemische Berichte; vol. 103; (1970); p. 1397 - 1411 View in Reaxys Kanaoka et al.; Chemical and Pharmaceutical Bulletin; vol. 18; (1970); p. 397,398 View in Reaxys Pedersen; Lawesson; Tetrahedron; vol. 29; (1973); p. 4205,4208 View in Reaxys Patent; Merck and Co. Inc.; Rahway; N.J. (V.St.A.); DE2130709; (1971); ; vol. 76; nb. 113209; (1972) View in Reaxys Boyle; Grundon; Chemical Communications (London); (1967); p. 1137 View in Reaxys Hoefle; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 28; (1973); p. 831 View in Reaxys Glass; Hoy; Tetrahedron Letters; (1976); p. 1781 View in Reaxys Spagnolo et al.; Journal of the Chemical Society [Section] B: Physical Organic; (1971); p. 2006 View in Reaxys Mndzhoyan; Pogosyan; Izvestiya Akademii Nauk Armyanskoi SSR, Khimicheskie Nauki; vol. 16; nb. 3; (1963); p. 263,264,265,266,267,268; ; vol. 60; nb. 6780c; (1964) View in Reaxys N

Rx-ID: 35356098 View in Reaxys 5/96

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Yield

Conditions & References With ammonium hydroxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, [{(MeOH)Cu(OAc)}(μ-k2:k1-2-(3-(pyridin-2yl)-1H-pyrazol-1-yl)acetic acid(-H))]2*0.5H2O, tetraethylammonium iodide, oxygen, potassium carbonate in water, Time= 24h,

93 %

T= 60 °C , p= 760.051Torr Xie, Jing-Bo; Bao, Jia-Jing; Li, Hong-Xi; Tan, Da-Wei; Li, Hai-Yan; Lang, Jian-Ping; RSC Advances; vol. 4; nb. 96; (2014); p. 54007 - 54017 View in Reaxys 92 %

With ammonia, oxygen in tert-Amyl alcohol, water, Time= 24h, T= 130 °C , p= 3750.38Torr 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

90 %

With 2,3'-bipyridine, ammonium hydroxide, copper(l) iodide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, oxygen in ethanol, Time= 24h, T= 20 °C Yin, Weiyu; Wang, Chengming; Huang, Yong; Organic Letters; vol. 15; nb. 8; (2013); p. 1850 - 1853 View in Reaxys

89 %

With Iron(III) nitrate nonahydrate, ammonium hydroxide, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 12h, T= 20 °C Dighe, Shashikant U.; Chowdhury, Deepan; Batra, Sanjay; Advanced Synthesis and Catalysis; vol. 356; nb. 18; (2014); p. 3892 - 3896 View in Reaxys

83 %

With potassium phosphate, ammonium formate in acetonitrile, Time= 16h, T= 115 °C , Sealed tube, Green chemistry Molla, Rostam Ali; Ghosh, Kajari; Tuhina; Manirul Islam; New Journal of Chemistry; vol. 39; nb. 2; (2015); p. 921 - 930 View in Reaxys

78 %

With copper(II) choride dihydrate, ammonium formate, potassium carbonate in neat (no solvent), Time= 24h, T= 135 °C , p= 760.051Torr , Sealed tube, Schlenk technique, Green chemistry Yadav, Dilip Kumar T.; Bhanage, Bhalchandra M.; European Journal of Organic Chemistry; nb. 23; (2013); p. 5106 - 5110 View in Reaxys N

Na + N

C–

Rx-ID: 35916895 View in Reaxys 6/96 Yield 74 %

Conditions & References With C18H14CuIN4 in acetonitrile, Time= 24h, T= 20 °C , Inert atmosphere, Sealed tube, UV-irradiation Kim, Kicheol; Hong, Soon Hyeok; Advanced Synthesis and Catalysis; vol. 359; nb. 14; (2017); p. 2345 - 2351 View in Reaxys Synthesis of 5-substituted-1H-tetrazoles (general procedure) General procedure: Synthesis of 5-substituted-1H-tetrazoles (general procedure): To a solution of aryliodide (1 mmol) in DMF (5 ml) was added sodium cyanide (1.2 mmol), catalyst(10 mol percent) and the reaction mixture was stirred under heating at 100° C for appropriate time to obtain nitrile compound (see Table 1). To the nitrile compound generated in situ was added sodium azide (1.5 mmol) and the reaction was continued till the complete conversion of nitrile to tetrazole. After the completion of the reaction, the catalyst from the reaction mixture was easily separated out by centrifuging the reaction mixture. After the separation of the catalyst the crude material was then taken into ethyl acetate and washed with 5 N HCl and the layers separated. The organic layer was then washed with water, dried over anhyd sodium sulfate and concentrated to obtain the crude product. The crude product was purified by silica gel column chromatography using appropriate solvent mixtures to obtain the pure products (see Tables 1and 2). Detailed experimental conditions and spectroscopic data were given insupplementary data. With copper(II) oxide in N,N-dimethyl-formamide, T= 100 °C

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Yapuri, Umanadh; Palle, Sadanandam; Gudaparthi, Omprakash; Narahari, Srinivasa Reddy; Rawat, Dhwajbahadur K.; Mukkanti, Khagga; Vantikommu, Jyothi; Tetrahedron Letters; vol. 54; nb. 35; (2013); p. 4732 - 4734 View in Reaxys

N O

O N

Rx-ID: 45014446 View in Reaxys 7/96 Yield

Conditions & References With potassium phosphate, [(Ph3P)2Ni(1-naphthyl)Cl], 1-deuteriodiphenylmethanol, C24H31N2 (1+)*Cl(1-) in toluene, Time= 15h,

83 %

T= 110 °C , Inert atmosphere Kuriyama, Masami; Kujirada, Shota; Tsukuda, Kotaro; Onomura, Osamu; Advanced Synthesis and Catalysis; vol. 359; nb. 6; (2017); p. 1043 - 1048 View in Reaxys

NH 2

Rx-ID: 45087329 View in Reaxys 8/96 Yield

Conditions & References

77 %

Typical procedures for Cu-catalyzed aerobic oxidation of primary amines with air for nitrile synthesis: General procedure: A mixture of benzylamine 1a (107.0 mg, 1.0 mmol), CuCl (5.0 mg, 0.05 mmol, 5 molpercent), 2,2,6,6-tetramethyl-1-piperidyloxy (TEMPO, 7.8 mg, 0.05 mmol, 5 molpercent), and N,N-dimethylethane-1,2-diamine (DMEDA, 4.4 mg, 0.05 mmol, 5 molpercent) in toluene (0.5 mL) sealed in a Schlenk tube (100 mL) with an air balloon was stirred at 80 °C for 24 h. The reaction was then monitored by TLC and/or GC-MS. After completion of the reaction, solvent was evaporated under vacuum. The residue was purified by scosh column chromatography on silica gel using petroleum ether and ethyl acetate (0– 100/1) as the eluent, giving product 2a in 80percent isolated yield With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, N,N-dimethylethylenediamine, copper(l) chloride in toluene, Time= 24h, T= 80 °C , Sealed tube, Schlenk technique, chemoselective reaction Ma, Xian-Tao; Xu, Hao; Xiao, Ying-Lin; Su, Chen-Liang; Liu, Jian-Ping; Xu, Qing; Chinese Chemical Letters; vol. 28; nb. 6; (2017); p. 1336 - 1339 View in Reaxys

55 %, 21 %

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, C63H51N2O3P2Ru(1+)*ClO4 (1-), oxygen in toluene, Time= 20h, T= 90 °C , p= 760.051Torr Ray, Ritwika; Chandra, Shubhadeep; Yadav, Vishal; Mondal, Prasenjit; Maiti, Debabrata; Lahiri, Goutam Kumar; Chemical Communications; vol. 53; nb. 28; (2017); p. 4006 - 4009 View in Reaxys O

N O

O –C

Zn 2+ O

Rx-ID: 45539213 View in Reaxys 9/96

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Yield

Conditions & References

76 %

With palladium diacetate, cyclohexyldiphenylphosphine in 1,4-dioxane, Time= 16h, T= 150 °C , Inert atmosphere, Schlenk technique, chemoselective reaction Shi, Shicheng; Szostak, Michal; Organic Letters; vol. 19; nb. 12; (2017); p. 3095 - 3098 View in Reaxys With potassium fluoride, bis(1,5-cyclooctadiene)nickel (0), 1,2-bis-(dicyclohexylphosphino)ethane in toluene, T= 170 °C , Glovebox, Sealed tube

36 %

Chatupheeraphat, Adisak; Liao, Hsuan-Hung; Lee, Shao-Chi; Rueping, Magnus; Organic Letters; vol. 19; nb. 16; (2017); p. 4255 - 4258 View in Reaxys O

N O

O –

C 2

N Zn 2+

Rx-ID: 45999676 View in Reaxys 10/96 Yield

Conditions & References

61 %

With manganese, nickel(II) bromide 2-methoxyethyl ether, 1,2-bis-(dicyclohexylphosphino)ethane in toluene, Time= 16h, T= 150 °C , Glovebox, Sealed tube Chatupheeraphat, Adisak; Liao, Hsuan-Hung; Lee, Shao-Chi; Rueping, Magnus; Organic Letters; vol. 19; nb. 16; (2017); p. 4255 - 4258 View in Reaxys N

Rx-ID: 364394 View in Reaxys 11/96 Yield 95 %

Conditions & References With acetonitrile, Time= 2h, Reflux, Green chemistry Zarghani, Monireh; Akhlaghinia, Batool; Applied Organometallic Chemistry; vol. 29; nb. 10; (2015); p. 683 - 689 View in Reaxys

90 %

With thionyl chloride, sodium sulfite, Time= 0.166667h, T= 0 °C Kiasat, Ali Reza; Kazemi, Foad; Khosravian, Forogh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 178; nb. 6; (2003); p. 1377 - 1383 View in Reaxys

90 %

With thionyl chloride, silica gel in dichloromethane, Time= 0.25h, T= 0 °C Kazemi, Foad; Kiasat, Ali Reza; Fadavipoor, Elham; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 179; nb. 2; (2004); p. 433 - 436 View in Reaxys

90 %

Procedure for the synthesis of nitrile from aldoxime General procedure: Aldoxime (1.0 mmol) and anhydrous FeCl3 (1.0 mmol) were intimately mixed with silica gel 60–120 mesh (1.0 g) in mortar and pestle. The resulting solid mixture was poured into a round-bottom flask (50 ml) and allowed to stir on magnetic stirrer at 110 °C for an appropriate time (Table 2). The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 15 ml) and washed several times with water. The combined organic mixture was dried over anhydrous Na2SO4, concentrated, and purified by column chromatography on silica gel 60–120 mesh using petroleum ether/ethyl acetate as eluent to afford pure nitrile. With iron(III) chloride, silica gel in neat (no solvent), Time= 3.5h, T= 110 °C , Green chemistry

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Ghosh, Pranab; Pariyar, Gyan Chandra; Saha, Bittu; Subba, Raju; Synthetic Communications; vol. 46; nb. 8; (2016); p. 685 - 691 View in Reaxys 89 %

With eosin, carbon tetrabromide, N,N-dimethyl-formamide in acetonitrile, Time= 14h, T= 25 °C , Irradiation, Inert atmosphere Yadav, Arvind K.; Srivastava, Vishnu P.; Yadav, Lal Dhar S.; RSC Advances; vol. 4; nb. 8; (2014); p. 4181 - 4186 View in Reaxys

88 %

With trichloro(trifluoromethanesulfonato)titanium(IV), 1-n-butyl-3-methylimidazolim bromide, Time= 2h Noei, Jalil; Khosropour, Ahmad Reza; Mirjafari, Arsalan; Bulletin of the Korean Chemical Society; vol. 33; nb. 6; (2012); p. 2102 - 2104 View in Reaxys

87 %

With oxalyl dichloride, 2,3-bis(4-methoxyphenyl)cyclopropenone, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 4h, Reflux Rai, Ankita; Yadav, Lal Dhar S.; European Journal of Organic Chemistry; nb. 10; (2013); p. 1889 - 1893 View in Reaxys

80 %

The general procedure of n-C4F9SO2F-induced dehydration of a variety of aldoximes to nitriles: General procedure: at room temperature, n-C4F9SO2F (20.0mmol, 2.0equiv.) was slowly dropped via syringe into a solution of substrate 1a (10.0mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 50.0mmol, 5.0equiv.) in CH2Cl2 (20mL). The resulting solution was stirred at this temperature for 10min. Evaporation under vacuum to remove volatile components offered residue which was purified through silica gel column chromatography (eluted with a mixture of petroleum ether and ethyl acetate), generating nitrile 2a in 95percent yield. With Nonafluorobutanesulfonyl fluoride, 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane, Time= 0.166667h, T= 20 °C Yan, Zhao-Hua; Tian, Huan; Zhao, Dong-Dong; Jin, Hong-Ai; Tian, Wei-Sheng; Chinese Chemical Letters; vol. 27; nb. 1; (2016); p. 96 - 98 View in Reaxys

71 %

2.2. Typical procedures for the synthesis of nitriles from aldoximes General procedure: Aldoxime (0.25 mmol), cobalt acetate(II) tetrahydrate (6.2 mg, 0.025 mmol), 2,4-dinitrophenol (9.2 mg, 0.05 mmol) and acetonitrile/H2O (0.49 + 0.01 mL, 2 v/vpercent of water in acetonitrile) were added to an oven-dried vial. The mixture was vigorously stirred at 80 °C for 24 h and then diluted with ethyl acetate. Solvent was removed invacuo, and the desired product was purified and isolated by silica gel column chromatography (ethyl acetate/n-hexane). With 2,4-Dinitrophenol, cobalt(II) diacetate tetrahydrate in water, acetonitrile, Time= 24h, T= 80 °C Jang, Wonseok; Kim, Se Eun; Yang, Cheol Mo; Yoon, Sungwoo; Park, Myunghwan; Lee, Junseong; Kim, Youngjo; Kim, Min; Catalysis Communications; vol. 60; (2015); p. 120 - 123 View in Reaxys With sodium acetate, acetic anhydride Curd; Raison; Journal of the Chemical Society; (1947); p. 160,162 View in Reaxys With thionyl chloride in benzene, Heating Master, Hoshang E.; Khan, Shabana I.; Poojari, Krishna A.; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 7; (2003); p. 1249 - 1251 View in Reaxys Master, Hoshang E.; Khan, Shabana I.; Poojari, Krishna A.; Bioorganic and Medicinal Chemistry; vol. 13; nb. 16; (2005); p. 4891 - 4899 View in Reaxys With trichlorothiophosphine, water, triethylamine, Neat (no solvent) Pandey, Lokesh Kumar; Pathak, Uma; Mathur, Sweta; Suryanarayana; Synthesis; vol. 44; nb. 3; (2012); p. 377 - 379; Art.No: H102311SS View in Reaxys

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K+ -4 N

N (v6)

N N N

Rx-ID: 33236827 View in Reaxys 12/96 Yield

Conditions & References

68 %

26 : Example 26: Photocatalytic Synthesis of Compound 3-Methoxybenzonitrile To a 25 mL screw test tube was added 0.25 mmol of 3-methoxybromobenzene, O.lmmol of cyanoating agent K4 [Fe (CN) 6], sodium acetate 0.25 mmo 1,100 mg of 3 wtpercent Pd / CeO2, 7 mL of N, N-dimethylformamide and lmL isopropanol into a test tube, 500W visible light irradiation under the magnetic stirring reaction to control the visible light intensity of 0.74W / Cm2, the reaction temperature of 55 ° C, 12 hours after the reaction to stop the reaction, take a small amount of reaction solution by microporous membrane filtration, methanol Dilution of the liquid phase to be measured samples, the sample to be tested and 3methoxy bromide standard, 3-methoxy benzonitrile standard for efficient The conversion of the reaction substrate was 80.5percent, the selectivity of the target product was 87.3percent, and the target product was liquid phase Rate of 70.3percent. Posttreatment method for the use of cloth funnel filter washing catalyst, drying for recycling use; reaction by two Methyl chloride and water, the organic layer was concentrated and the final product was obtained by column chromatography. 3-Methoxy Benzonitrile, the isolated yield was 68percent With 3% Pd/CeO2, sodium acetate in N,N-dimethyl-formamide, isopropyl alcohol, Time= 12h, T= 55 °C , Irradiation Patent; Nanjing University of Technology; Guo, Cheng; Gong, Xubin; Wu, Lou; Li, Qing; Wang, Jianjiang; (11 pag.); CN105777579; (2016); (A) Chinese View in Reaxys

56 %

With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2, potassium carbonate in N,N-dimethyl-formamide, Time= 0.25h, T= 130 °C , Microwave irradiation Hajipour, Abdol-Reza; Abrisham, Fatemeh; Tavakoli, Ghazal; Transition Metal Chemistry; vol. 36; nb. 7; (2011); p. 725 730 View in Reaxys OH B

N O

Rx-ID: 41989245 View in Reaxys 13/96 Yield

Conditions & References

80 %

With chloro(1,5-cyclooctadiene)rhodium(I) dimer, caesium carbonate in 1,4-dioxane, Time= 6h, T= 100 °C , Inert atmosphere Malapit, Christian A.; Reeves, Jonathan T.; Busacca, Carl A.; Howell, Amy R.; Senanayake, Chris H.; Angewandte Chemie - International Edition; vol. 55; nb. 1; (2016); p. 326 - 330; Angew. Chem.; vol. 128; nb. 1; (2016); p. 334 - 338 View in Reaxys N

Rx-ID: 42199577 View in Reaxys 14/96 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= 8h, T= 55 °C , p= 750.075Torr , Green chemistry, Overall yield = 49.5 percent Zhang, Yuecheng; Huang, Rong; Gao, Baosheng; Zhao, Jiquan; Catalysis Letters; vol. 146; nb. 1; (2016); p. 220 - 228

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View in Reaxys N N

N O

Rx-ID: 43518207 View in Reaxys 15/96 Yield

Conditions & References

65 %

With potassium phosphate, 3,4-bis-(dicyclohexylphosphino)thiophene, nickel dibromide, zinc in toluene, Time= 18h, T= 150 °C , Inert atmosphere, Sealed tube Takise, Ryosuke; Itami, Kenichiro; Yamaguchi, Junichiro; Organic Letters; vol. 18; nb. 17; (2016); p. 4428 - 4431 View in Reaxys 4

K+ -4 N

N O

N (v6)

N N N

Rx-ID: 44580545 View in Reaxys 16/96 Yield

Conditions & References

26 %

5 : Example 5: Photocatalytic Synthesis of Compound 3-Methoxybenzonitrile To a 25 mL screw test tube was added 0.25 mmol of 3-methoxyiodobenzene, O.lmmol of cyanoating agent K4 [Fe (CN) 6], sodium acetate 0.3 mmol, 100 mg of 3 wtpercent Pd / CeO2, Propanol as organic solvent to test tube, 500W visible light irradiation under the magnetic stirring reaction, control visible light intensity of 0.74W / cm2, the reaction temperature of 75 ° C, 12 hours after the reaction to stop the reaction, take a small amount of reaction by micro Pore filter, methanol solvent dilution obtained by the liquid phase to be measured samples, the sample to be tested and 3-methoxy iodobenzene standard, 3-methoxy benzonitrile standard for high-performance liquid phase detection and comparison of reaction at the end The conversion of the product was 34.9percent, the selectivity of the target product was 82.1percent, and the liquid product yield was 28.7percent. The reaction solution was extracted with a mixed solution of dichloromethane and water, and then the organic layer was extracted and the final product was obtained by column chromatography. The reaction mixture was washed with a mixture of dichloromethane and water. Methoxybenzonitrile, the isolated yield was 26percent. With 3% Pd/CeO2, sodium acetate in isopropyl alcohol, Time= 12h, T= 75 °C , Irradiation Patent; Nanjing University of Technology; Guo, Cheng; Gong, Xubin; Wu, Lou; Li, Qing; Wang, Jianjiang; (11 pag.); CN105777579; (2016); (A) Chinese View in Reaxys O

Rx-ID: 30636238 View in Reaxys 17/96 Yield 88 %

Conditions & References Stage 1: With magnesium, lithium chloride in tetrahydrofuran, T= 20 °C , Inert atmosphere Stage 2: in tetrahydrofuran, T= 0 - 20 °C , Inert atmosphere Anbarasan, Pazhamalai; Neumann, Helfried; Beller, Matthias; Chemistry - A European Journal; vol. 17; nb. 15; (2011); p. 4217 - 4222 View in Reaxys

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0.19 g

Stage 1: With 3-chloroprop-1-ene, trifluoroacetic acid, cobalt(II) bromide, zinc in acetonitrile, T= 20 °C , Knochel Zinc Vinyl Coupling Stage 2: With zinc in acetonitrile, T= 0 - 50 °C , Inert atmosphere Cai, Yingxiao; Qian, Xin; Rrat, Alice; Auffrant, Audrey; Gosmini, Corinne; Advanced Synthesis and Catalysis; vol. 357; nb. 16-17; (2015); p. 3419 - 3423 View in Reaxys N

Rx-ID: 31066011 View in Reaxys 18/96 Yield

Conditions & References

81 %

With sodium azide, palladium diacetate, XPhos in acetone, Time= 6h, T= 80 °C , Inert atmosphere Zou, Tao; Yu, Xiaoqiang; Feng, Xiujuan; Bao, Ming; Chemical Communications; vol. 51; nb. 53; (2015); p. 10714 - 10717 View in Reaxys Reaction Steps: 2 1: tetrabutylammoniun azide / toluene / 8 h / 80 °C / 760.05 Torr 2: Al2O3-supported ruthenium hydroxide; air / toluene / 5 h / 80 °C / 760.05 Torr With tetrabutylammoniun azide in toluene He, Jinling; Yamaguchi, Kazuya; Mizuno, Noritaka; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4606 - 4610 View in Reaxys

Rx-ID: 39717638 View in Reaxys 19/96 Yield

Conditions & References

1.21 g

With 4-(acetylamino)-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate in dichloromethane, Time= 12h, T= 20 °C Kelly, Christopher B.; Lambert, Kyle M.; Mercadante, Michael A.; Ovian, John M.; Bailey, William F.; Leadbeater, Nicholas E.; Angewandte Chemie - International Edition; vol. 54; nb. 14; (2015); p. 4241 - 4245 View in Reaxys

OH B

N O

Rx-ID: 41093102 View in Reaxys 20/96 Yield 85 %

Conditions & References With N-iodo-succinimide, 1,10-Phenanthroline, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical, 1,1,1,2,2,2-hexamethyldisilane, oxygen, copper diacetate, diisopropylamine, T= 20 - 150 °C , Schlenk technique Zhu, Yamin; Li, Linyi; Shen, Zengming; Chemistry - A European Journal; vol. 21; nb. 38; (2015); p. 13246 - 13252 View in Reaxys

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Rx-ID: 41102550 View in Reaxys 21/96 Yield

Conditions & References

88 %

Stage 1: With TurboGrignard in tetrahydrofuran, 1,4-dioxane, Time= 48h, T= 0 °C Stage 2: in tetrahydrofuran, 1,4-dioxane, Time= 0.5h, T= 0 - 23 °C Reeves, Jonathan T.; Malapit, Christian A.; Buono, Frederic G.; Sidhu, Kanwar P.; Marsini, Maurice A.; Sader, C. Avery; Fandrick, Keith R.; Busacca, Carl A.; Senanayake, Chris H.; Journal of the American Chemical Society; vol. 137; nb. 29; (2015); p. 9481 - 9488 View in Reaxys

O NH 2

Rx-ID: 41683521 View in Reaxys 22/96 Yield

Conditions & References

57 %

With oxygen in water, acetonitrile, Time= 1h, T= 250 °C , p= 750.075Torr , Flow reactor, Catalytic behavior, Mechanism, Time, Solvent Corker, Emily C.; Ruiz-Martínez, Javier; Riisager, Anders; Fehrmann, Rasmus; Catalysis Science and Technology; vol. 5; nb. 11; (2015); p. 5008 - 5015 View in Reaxys

Rx-ID: 29601744 View in Reaxys 23/96 Yield 68 %

Conditions & References Typicalprocedures for benzylic nitriles General procedure: An undivided cell was equipped with a magnet stirrer, platinum electrodes as the working electrodes. A mixture of benzylic azides (0.5 mmol), electrolyte (0.25 mmol), and phrase transfer catalyst (PTC, 0.25 mmol) in distilled water (6 mL) was electrolyzed at a constant current of 25 mA and stirred simultaneously for 4 h at room temperature. Upon completion of the reaction, the mixture was diluted with ethyl acetate. The solvent was removed with the aid of a rotary evaporator. The residue was purified by column chromatography on silica gel and characterized by NMR spectroscopy. With K3PO4*3H2O, tetrabutylammomium bromide in water, Time= 4h, T= 20 °C , Electrochemical reaction, Green chemistry Ye, Jia-Qian; Zhang, Zhen-Lei; Zha, Zheng-Gen; Wang, Zhi-Yong; Chinese Chemical Letters; vol. 25; nb. 8; (2014); p. 1112 - 1114 View in Reaxys

44 mg

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,2-dichloro-ethane, Time= 10h, Inert atmosphere, Reflux Zhou, Wang; Xu, Jiaojiao; Zhang, Liangren; Jiao, Ning; Organic Letters; vol. 12; nb. 12; (2010); p. 2888 - 2891 View in Reaxys

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86 %Chromat.

With Al2O3-supported ruthenium hydroxide, air in toluene, Time= 5h, T= 80 °C , p= 760.051Torr He, Jinling; Yamaguchi, Kazuya; Mizuno, Noritaka; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4606 - 4610 View in Reaxys

N N

(v6) Fe 4-

O N

N K+

Rx-ID: 29982609 View in Reaxys 24/96 Yield

Conditions & References

85 %

general procedures for the cyanation of aryl chlorides and mesylates General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with Pd(OAc)2 (4.5 mg, 0.02 mmol ), L1 (36.5 mg, 0.08 mmol), PhB(OH)2 (6.1 mg, 0.05 mmol), and t-BuOH (2 mL), and the mixture was stirred for half hour at 50 °C. After cooling to r.t., aryl chloride or mesylates (1.00 mmol), K4[Fe(CN)6]·3H2O (211.2 mg, 0.50 mmol), K2CO3 (138.2 mg, 1.00 mmol), and H2O (2 mL) were added. The septum was replaced with an inside reflux condenser, and then the Schlenk tube was placed in an oil bath preheated to 100 °C (120 °C for aryl mesylates) with stirring for 6 h (24 h for aryl mesylates). Then the reaction mixture was allowed to cool to r.t., extracted with CH2Cl2, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel. With di-tert-butyl{2κ-isopropoxy-[1,1κ-binaphthalen]-2-yl}phosphane, palladium diacetate, potassium carbonate, phenylboronic acid in water, tert-butyl alcohol, Time= 6h, T= 100 °C , Inert atmosphere, Schlenk technique, Suzuki-Miyaura Coupling Tu, Yahui; Zhang, Yi; Xu, Sheng; Zhang, Zhaoguo; Xie, Xiaomin; Synlett; vol. 25; nb. 20; (2014); p. 2938 - 2942; Art.No: ST-2014-W0578-L View in Reaxys

97 %Chromat.

With palladium diacetate, potassium carbonate, XPhos in 1,4-dioxane, water, Time= 10h, T= 120 °C , sealed tube, Inert atmosphere Zhang, Junli; Chen, Xiaorong; Hu, Tongjie; Zhang, Yuan; Xu, Kunling; Yu, Yanpeng; Huang, Jun; Catalysis Letters; vol. 139; nb. 1-2; (2010); p. 56 - 60 View in Reaxys N

Rx-ID: 38312444 View in Reaxys 25/96 Yield

Conditions & References Reaction Steps: 2 1: sodium azide / dimethyl sulfoxide / 2 h 2: K3PO4*3H2O; tetrabutylammomium bromide / water / 4 h / 20 °C / Electrochemical reaction; Green chemistry With sodium azide, K3PO4*3H2O, tetrabutylammomium bromide in water, dimethyl sulfoxide Ye, Jia-Qian; Zhang, Zhen-Lei; Zha, Zheng-Gen; Wang, Zhi-Yong; Chinese Chemical Letters; vol. 25; nb. 8; (2014); p. 1112 - 1114 View in Reaxys N

O OH

N H

Rx-ID: 38750529 View in Reaxys 26/96

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Yield

Conditions & References

96 %

With 2,2,6,6-tetramethyl-piperidine-N-oxyl, [{Cu(NO3)}(μ-3-(6-(1H-pyrazol-1-yl)pyridin-2-yl)pyrazol-1-ide)]2, oxygen, potassium carbonate, Time= 24h, T= 50 °C Tan, Da-Wei; Xie, Jing-Bo; Li, Qi; Li, Hong-Xi; Li, Jun-Chi; Li, Hai-Yan; Lang, Jian-Ping; Dalton Transactions; vol. 43; nb. 37; (2014); p. 14061 - 14071 View in Reaxys N

O N

(v6) Fe 4-

O N

N N 4

K+

Rx-ID: 39111793 View in Reaxys 27/96 Yield

Conditions & References

85 %

general procedures for the cyanation of aryl chlorides and mesylates General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with Pd(OAc)2 (4.5 mg, 0.02 mmol ), L1 (36.5 mg, 0.08 mmol), PhB(OH)2 (6.1 mg, 0.05 mmol), and t-BuOH (2 mL), and the mixture was stirred for half hour at 50 °C. After cooling to r.t., aryl chloride or mesylates (1.00 mmol), K4[Fe(CN)6]·3H2O (211.2 mg, 0.50 mmol), K2CO3 (138.2 mg, 1.00 mmol), and H2O (2 mL) were added. The septum was replaced with an inside reflux condenser, and then the Schlenk tube was placed in an oil bath preheated to 100 °C (120 °C for aryl mesylates) with stirring for 6 h (24 h for aryl mesylates). Then the reaction mixture was allowed to cool to r.t., extracted with CH2Cl2, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel. With di-tert-butyl{2κ-isopropoxy-[1,1κ-binaphthalen]-2-yl}phosphane, palladium diacetate, potassium carbonate, phenylboronic acid in water, tert-butyl alcohol, Time= 24h, T= 120 °C , Inert atmosphere, Schlenk technique, Suzuki-Miyaura Coupling Tu, Yahui; Zhang, Yi; Xu, Sheng; Zhang, Zhaoguo; Xie, Xiaomin; Synlett; vol. 25; nb. 20; (2014); p. 2938 - 2942; Art.No: ST-2014-W0578-L View in Reaxys H

O 3

(v6)

K+

Fe 3-

N N

Rx-ID: 39177458 View in Reaxys 28/96 Yield 90 %

Conditions & References General procedure: Aryliodide (0.5 mmol), K4[Fe(CN)6]3H2O(0.15 mmol), K3PO4 (1.5 mmol) and Pd-BNP (5.3 mg, 0.005 mmol, 1.0 molpercent)were taken in a oven dried reaction tube equipped with magnetic pellet. DMF(2.0 mL) was added to the reaction tube and the reaction mixture was stirred at120 C temperature. The reaction was monitored by TLC. After consumption ofthe starting material, the reaction mixture was cooled to room temperature.Crude product was extracted with ethyl acetate (3 10 mL). Then the organicphase was dried over Na2SO4 and concentrated in vacuum. The product waspurified by column chromatography using silica gel. With potassium phosphate in N,N-dimethyl-formamide, Time= 2h, T= 120 °C Ganapathy, Dhandapani; Kotha, Surya Srinivas; Sekar, Govindasamy; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 172 178 View in Reaxys

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Rx-ID: 3862762 View in Reaxys 29/96 Yield

Conditions & References

81 %

With tert.-butylnitrite, N -hydroxyphthalimide, palladium diacetate in acetonitrile, Time= 24h, T= 70 °C , Inert atmosphere, Sealed tube Shu, Zhibin; Ye, Yuxuan; Deng, Yifan; Zhang, Yan; Wang, Jianbo; Angewandte Chemie - International Edition; vol. 52; nb. 40; (2013); p. 10573 - 10576; Angew. Chem.; vol. 125; nb. 40; (2013); p. 10767 - 10770,4 View in Reaxys

16.1 <unit not given>

With air, ammonia, vanadium-titanium oxide, Time= 0.000333333h, T= 383.9 °C Martin, A.; French, J.; Seeboth, H.; Luecke, B.; Fischer, E.; Journal fuer Praktische Chemie (Leipzig); vol. 332; nb. 4; (1990); p. 551 - 556 View in Reaxys

N N

(v6) 4-

O N

N 4

K+

Rx-ID: 30448079 View in Reaxys 30/96 Yield 92 %

Conditions & References With tris-(dibenzylideneacetone)dipalladium(0), tris(2-morpholinophenyl)phosphine, potassium carbonate in water, tert-butyl alcohol, Time= 15h, T= 85 °C , Schlenk technique, Inert atmosphere Zou, Tao; Feng, Xiujuan; Liu, Hesong; Yu, Xiaoqiang; Yamamoto, Yoshinori; Bao, Ming; RSC Advances; vol. 3; nb. 43; (2013); p. 20379 - 20384 View in Reaxys

87 %

2. General procedures for palladium-catalyzed cyanation of aryl bromides General procedure: An oven-dried Schlenk tube with the presence of magnetic stir bar which is Teflon-coated was charged with Pd(dba)2 (11.5 mg, 0.02 mmol, 2 molpercent) and ligand L4 (8.4 mg, 0.02 mmol, 2 molpercent). The flask was evacuated and backfilled with nitrogen (3 cycles). Pre-complexation of palladium and ligand was initiated by injecting freshly distilled dry dichloromethane (2.0 mL) and Et3N (0.1 mL) into the tube. The solution was stirred and warmed with hair drier till the solvent condensed on the tube wall. The solvent was removed under vacuum. Aryl bromide (1.0 mmol), KOt-Bu (0.25 mmol), and potassium hexacyanoferrate(II) trihydrate (0.23 mmol) were charged successively to the tube followed by another 3 evacuationnitrogen refill cycles. Water (1.0 mL) and acetonitrile (1.0 mL) were used as a solvent mixture. The tube was immersed into a preheated 50 °C oil bath for 24 hours. The reaction was quenched by cooling to ambient temperature and added with EtOAc and water. The organic supernatant was analyzed by GC. The organic layer was separated and the remained aqua medium was further extracted with EtOAc (10 mL .x. 3). The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (230-400 mesh). The pure fractions were collected, dried under vacuum, and followed by proton (1H) and carbon (13C) NMR characterization With 2-(2-methoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole, potassium tert-butylate, triethylamine, bis(dibenzylideneacetone)-palladium(0) in dichloromethane, water, acetonitrile, Time= 24h, T= 50 °C , Inert atmosphere Yeung, Pui Yee; Tsang, Chun Pui; Kwong, Fuk Yee; Tetrahedron Letters; vol. 52; nb. 52; (2011); p. 7038 - 7041 View in Reaxys

80 %

General procedure for cyanation reaction of aryl halides with K4[Fe(CN)6] under microwave irradiation General procedure: A mixture of the aryl halide (1 mmol), K4[Fe(CN)6]*3 H2O (0.22 mmol, 92.9 mg), TBAB (1 mmol, 322.4 mg), palladacycle catalyst (0.5 mmol percent, 4.7 mg), and K2CO3 (1 mmol, 138.2 mg) was added to DMF (3 mL) in a roundbottomed flask equipped with a condenser and placed into the Milestone microwave. Initially using a microwave power of 600 W the temperature was ramped from room temperature to 130 °C, this taking approximately 1 min, and then held at this temper-

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ature until the reaction was completed. During this time, the power was modulated automatically to keep the reaction mixture at 130 °C. The mixture was stirred continuously using an appropriate magnet during the reaction. After the reaction was completed, the mixture was cooled to room temperature and diluted with water (30 ml) and ethyl acetate (30 ml). The organic layer was dried over MgSO4, filtered, and the solvent was evaporated using rotary evaporator. The residue was purified by silica gel column chromatography or by recrystallization using ethanol and water. The products were characterized by comparing their mp, IR, 1H, 13C NMR spectra with those found in the literature. [19] and [20] With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2, tetrabutylammomium bromide, potassium carbonate in N,N-dimethyl-formamide, Time= 0.133333h, T= 130 °C , Microwave irradiation Hajipour, Abdol Reza; Rafiee, Fatemeh; Ruoho, Arnold E.; Tetrahedron Letters; vol. 53; nb. 5; (2012); p. 526 - 529 View in Reaxys 65 %

With potassium phosphate, 2-pyridinecarboxaldehyde N-methyl-N-phenylhydrazone, palladium(II) trifluoroacetate in N,N-dimethyl-formamide, Time= 18h, T= 110 °C Mino, Takashi; Koizumi, Tomoko; Shibuya, Masanori; Hirai, Kiminori; Sakamoto, Masami; Fujita, Tsutomu; Heterocycles; vol. 83; nb. 1; (2011); p. 163 - 169 View in Reaxys N O

O–

K+

Rx-ID: 35057418 View in Reaxys 31/96 Yield 64 %

Conditions & References With oxygen, copper diacetate, silver carbonate in N,N-dimethyl-formamide, Time= 36h, T= 140 °C , p= 760.051Torr Bhadra, Sukalyan; Dzik, Wojciech I.; Gooßen, Lukas J.; Angewandte Chemie - International Edition; vol. 52; nb. 10; (2013); p. 2959 - 2962; Angew. Chem.; vol. 125; nb. 10; (2013); p. 3031 - 3035,4 View in Reaxys

64 %

Procedure 2a General procedure for the aryl ether synthesis via ortho-directed alkoxylation General procedure: A 70 mL teflon-screw capped schlenk tube was charged with potassium carboxylate (1l-z) (1.00 mmol), copper(II) acetate (46 mg, 0.25 mmol), silver carbonate (276 mg, 1 mmol), and alkoxy borane (4a-h) (1.2 mmol). Anhydrous DMF (5 mL) was added, the reaction vessel was briefly purged with oxygen, and the resulting mixture was stirred at 140 °C for 36 h. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (20 mL) and washed with saturated aqueous sodium bicarbonate (20 mL). The aqueous layer was extracted with diethyl ether (3 x 20 mL), and the combined organic layers were washed with water, 5 N HCl and brine, dried over MgSO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography on silica gel to yield the corresponding aryl ether (3la...3xh). With oxygen, copper diacetate, silver carbonate in N,N-dimethyl-formamide, Time= 36h, T= 140 °C , p= 750.075Torr , ChanLam Coupling, regiospecific reaction Bhadra, Sukalyan; Dzik, Wojciech I.; Goossen, Lukas J.; Synthesis (Germany); vol. 45; nb. 17; (2013); p. 2387 - 2390; Art.No: SS-2013-Z0414-PSP View in Reaxys N O

O N HO

Rx-ID: 35057464 View in Reaxys 32/96 Yield

Conditions & References Reaction Steps: 2 1: potassium tert-butylate / ethanol / 1 h 2: copper diacetate; silver carbonate; oxygen / N,N-dimethyl-formamide / 36 h / 140 °C / 760.05 Torr With potassium tert-butylate, oxygen, copper diacetate, silver carbonate in ethanol, N,N-dimethyl-formamide

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Bhadra, Sukalyan; Dzik, Wojciech I.; Gooßen, Lukas J.; Angewandte Chemie - International Edition; vol. 52; nb. 10; (2013); p. 2959 - 2962; Angew. Chem.; vol. 125; nb. 10; (2013); p. 3031 - 3035,4 View in Reaxys

N O

Si O

Rx-ID: 35356946 View in Reaxys 33/96 Yield

Conditions & References

76 %

With ammonium iodide, potassium fluoride, copper(II) nitrate trihydrate, oxygen, Time= 25h, T= 140 °C , Schlenk technique Wang, Zhen; Chang, Sukbok; Organic Letters; vol. 15; nb. 8; (2013); p. 1990 - 1993 View in Reaxys O N O

Rx-ID: 35654341 View in Reaxys 34/96 Yield 51 %

Conditions & References With N-iodo-succinimide, trimethylsilylazide in 1,2-dichloro-ethane, acetonitrile, Time= 3h, T= 20 - 70 °C Okamoto, Noriko; Ishikura, Minoru; Yanada, Reiko; Organic Letters; vol. 15; nb. 11; (2013); p. 2571 - 2573 View in Reaxys N

O O

Rx-ID: 35654351 View in Reaxys 35/96 Yield 73 %, 81 %

O N

Rx-ID: 35654364 View in Reaxys 36/96 Yield 61%, 62 %Chromat.

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B Si

Rx-ID: 36172218 View in Reaxys 37/96 Yield

Conditions & References

85 %

With copper(I) oxide, oxygen, N,N`-dimethylethylenediamine in acetonitrile, Time= 12h, T= 25 °C , Schlenk technique Ye, Yong; Wang, Yanhua; Liu, Pengtang; Han, Fushe; Chinese Journal of Chemistry; vol. 31; nb. 1; (2013); p. 27 - 30 View in Reaxys N

HO N

Rx-ID: 32673348 View in Reaxys 38/96 Yield

Conditions & References

60 %

With 5-(di(adamantan-1-yl)phosphino)-1κ,3κ,5κ-triphenyl-1κH-1,4κ-bipyrazole, palladium diacetate, caesium carbonate in toluene, Time= 12h, T= 80 °C Gowrisankar, Saravanan; Neumann, Helfried; Beller, Matthias; Chemistry - A European Journal; vol. 18; nb. 9; (2012); p. 2498 - 2502 View in Reaxys N

Cl O

Rx-ID: 32673355 View in Reaxys 39/96 Yield

Conditions & References

54 %

With 5-(di(adamantan-1-yl)phosphino)-1κ,3κ,5κ-triphenyl-1κH-1,4κ-bipyrazole, palladium diacetate, caesium carbonate in toluene, T= 80 °C Gowrisankar, Saravanan; Neumann, Helfried; Beller, Matthias; Chemistry - A European Journal; vol. 18; nb. 9; (2012); p. 2498 - 2502 View in Reaxys OH B

N O

Rx-ID: 32757766 View in Reaxys 40/96 Yield

Conditions & References

85 %

With ammonium iodide, copper(II) nitrate trihydrate, oxygen, acetic acid, Time= 18h, T= 130 °C Kim, Jinho; Choi, Jiho; Shin, Kwangmin; Chang, Sukbok; Journal of the American Chemical Society; vol. 134; nb. 5; (2012); p. 2528 - 2531 View in Reaxys N

Rx-ID: 32834824 View in Reaxys 41/96

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Yield

Conditions & References

82 %

With potassium fluoride, 1,10-Phenanthroline, copper diacetate, sodium t-butanolate in N,N-dimethyl-formamide, Time= 18h, T= 120 °C Jiang, Zhaoqiong; Huang, Qing; Chen, Si; Long, Lasheng; Zhou, Xiangge; Advanced Synthesis and Catalysis; vol. 354; nb. 4; (2012); p. 589 - 592 View in Reaxys 3

K+ -3

HO (v6)

N N N

Rx-ID: 33850540 View in Reaxys 42/96 Yield

Conditions & References

58 %Chromat.

With iodine, palladium diacetate, copper(II) acetate monohydrate, potassium carbonate in dimethyl sulfoxide, Time= 12h, T= 160 °C , Inert atmosphere Tian, Xinzhe; Sun, Yanpei; Dong, Chuanhua; Zhang, Kaixuan; Liang, Tengfei; Zhang, Yu; Hou, Chaodong; Chemistry Letters; vol. 41; nb. 7; (2012); p. 719 - 721 View in Reaxys N

Br 2H

2H 2H

Rx-ID: 34238981 View in Reaxys 43/96 Yield

Conditions & References

69 %

With palladium diacetate, caesium carbonate, tert-butyl XPhos in toluene, Time= 12h, T= 80 °C Dash, Pragyanditi; Janni, Manojkumar; Peruncheralathan, S.; European Journal of Organic Chemistry; nb. 26; (2012); p. 4914 - 4917,4 View in Reaxys Dash, Pragyanditi; Janni, Manojkumar; Peruncheralathan; European Journal of Organic Chemistry; nb. 26; (2012); p. 4914 - 4917 View in Reaxys N

Rx-ID: 31066012 View in Reaxys 44/96 Yield

Conditions & References

81 %Chromat., 7 %Chromat.

With tetrabutylammoniun azide in toluene, Time= 8h, T= 80 °C , p= 760.051Torr He, Jinling; Yamaguchi, Kazuya; Mizuno, Noritaka; Journal of Organic Chemistry; vol. 76; nb. 11; (2011); p. 4606 - 4610 View in Reaxys N

Na + N

C–

Rx-ID: 31395136 View in Reaxys 45/96

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Yield

Conditions & References

99 %

With tri-tert-butyl phosphine, [Pd2(dba)5], zinc in tetrahydrofuran, acetonitrile, Time= 2h, T= 70 °C Ushkov, Alexander V.; Grushin, Vladimir V.; Journal of the American Chemical Society; vol. 133; nb. 28; (2011); p. 10999 11005 View in Reaxys N

O -1 6 N 4

Fe 2+

K+

Rx-ID: 28752931 View in Reaxys 46/96 Yield

Conditions & References

83 %

With palladium(II) trifluoroacetate, tri-tert-butylphosphonium tetrafluoroborate, sodium carbonate in N,N-dimethyl acetamide, Time= 16h, T= 140 °C , Inert atmosphere Schareina, Thomas; Jackstell, Ralf; Schulz, Thomas; Zapf, Alexander; Cotte, Alain; Gotta, Matthias; Beller, Matthias; Advanced Synthesis and Catalysis; vol. 351; nb. 4; (2009); p. 643 - 648 View in Reaxys NH 2

OH O

Rx-ID: 28828090 View in Reaxys 47/96 Yield

Conditions & References With ammonia, oxygen in tetrahydrofuran, Time= 5h, T= 120 °C , p= 4560.31Torr Oishi, Takamichi; Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie, International Edition; vol. 48; nb. 34; (2009); p. 6286 - 6288; Angewandte Chemie; vol. 121; nb. 34; (2009); p. 6404 - 6406 View in Reaxys

O H

N O

NH HN O

N O O

Rx-ID: 28231831 View in Reaxys 48/96 Yield 79 %, 18 %

Conditions & References With lithium diisopropyl amide in tetrahydrofuran, hexanes, Time= 1h, T= 0 °C , Inert atmosphere Di Nunno, Leonardo; Vitale, Paola; Scilimati, Antonio; Tetrahedron; vol. 64; nb. 49; (2008); p. 11198 - 11204 View in Reaxys

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NH 2

Rx-ID: 28417092 View in Reaxys 49/96 Yield

Conditions & References

87 %

With water, oxygen, Time= 10h, T= 140 °C , p= 3800.26Torr Kim, Jung Won; Yamaguchi, Kazuya; Mizuno, Noritaka; Angewandte Chemie - International Edition; vol. 47; nb. 48; (2008); p. 9249 - 9251 View in Reaxys N

Rx-ID: 9248141 View in Reaxys 50/96 Yield

Conditions & References

86 %

With per-rhenic acid in water, 1,3,5-trimethyl-benzene, Time= 1h, Heating Ishihara, Kazuaki; Furuya, Yoshiro; Yamamoto, Hisashi; Angewandte Chemie - International Edition; vol. 41; nb. 16; (2002); p. 2983 - 2986 View in Reaxys

86 %

With per-rhenic acid in water, 1,3,5-trimethyl-benzene, Time= 1h, Heating Furuya, Yoshiro; Ishihara, Kazuaki; Yamamoto, Hisashi; Bulletin of the Chemical Society of Japan; vol. 80; nb. 2; (2007); p. 400 - 406 View in Reaxys N

(v2)

Rx-ID: 9772735 View in Reaxys 51/96 Yield

Conditions & References With water, tri tert-butylphosphoniumtetrafluoroborate, zinc, tris(dibenzylideneacetone)dipalladium(0) chloroform complex in 1methyl-pyrrolidin-2-one, Time= 24h, T= 20 °C

74 %

Stazi, Federica; Palmisano, Giovanni; Turconi, Marco; Santagostino, Marco; Tetrahedron Letters; vol. 46; nb. 11; (2005); p. 1815 - 1818 View in Reaxys 63 %

With 1,1'-bis-(diphenylphosphino)ferrocene, polymethylhydrosiloxane, palladium diacetate in water, Time= 3h, T= 120 °C Martin, Michael T.; Liu, Bing; Cooley Jr., Bobby E.; Eaddy, John F.; Tetrahedron Letters; vol. 48; nb. 14; (2007); p. 2555 2557 View in Reaxys N

Rx-ID: 10291720 View in Reaxys 52/96

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Yield

Conditions & References

44 % Chromat., 30 % Chromat.

With 2,3-dicyano-5,6-dichloro-p-benzoquinone in acetonitrile, Time= 0.5h, Photolysis, Title compound not separated from byproducts De Lijser, H.J. Peter; Hsu, Susan; Marquez, Bernadette V.; Park, Adriana; Sanguantrakun, Nawaporn; Sawyer, Jody R.; Journal of Organic Chemistry; vol. 71; nb. 20; (2006); p. 7785 - 7792 View in Reaxys N

13C

O N

13C

Rx-ID: 3959023 View in Reaxys 53/96 Yield

Conditions & References

80 %

5 : Scheme 11 The required 13C-labelled bromide (54) can be prepared using a similar procedure to that employed above, starting from the commercially available iodide (57) via the nitrile (58), as shown in Scheme 12. With calcium hydroxide, palladium diacetate in DMF (N,N-dimethyl-formamide) Patent; THE UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; WO2004/69774; (2004); (A2) English View in Reaxys

74.3 %

With copper(l) iodide in various solvent(s), Time= 3h, T= 210 °C Carr; Cable; Wells; Sutherland; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 34; nb. 9; (1994); p. 887 897 View in Reaxys

64 %

With calcium hydroxide, palladium diacetate in N,N-dimethyl-formamide, Time= 24h, Heating Fryatt, Tara; Botting, Nigel P.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 48; nb. 13; (2005); p. 951 969 View in Reaxys

63 %

5.b :Potassium [13C] cyanide (0.5 g, 7.4 mmol) was added to a solution of 3-iodoanisole (1.73 g, 7.4 mmol), palladium acetate (0.25 g, 1.13 mmol) and calcium hydroxide (0.28 g, 3.7 mmol) in dry DMF (50 ml) and the mixture was heated under reflux for 24 h. After cooling the DMF was removed in vacuo. Water (50 ml) was added and the mixture was extracted with ether (3x 50 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (light petroleum/ether (95: 5) elution) to give the title compound as a yellow oil (0.62 g, 63percent), (HRMS Found M+, 134.0565. C7L3CH7NO requires 134.0561) ; VMAX (NEAT)/CM~L 2179 (CN) and 1579 (C=C); 8H (300 MHZ ; CDC13) 3.82 (3H, s, OMe), 7.11-7. 14 (2H, m, H-2,6), 7.23-7. 25 (1H, m, H-4) and 7.33-7. 37 (1H, m, H-5) ; 8C (75 MHz; CDC13) 55.5 (OMe), 116.9 (C-4), 118.8 (13CN), 119.4 (C-2), 124.6 (C-5), 130.4 (C-6) and 159.8 (C-3'); m/z (EI) 134 (M+, 100percent), 104 (55), 91 (43), 77 (13), 63 (17) and 50 (9). With calcium hydroxide, palladium diacetate in DMF (N,N-dimethyl-formamide), Time= 24h, Heating / reflux Patent; THE UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; WO2004/69774; (2004); (A2) English View in Reaxys N

OH N

Rx-ID: 9333421 View in Reaxys 54/96 Yield 79 %

Conditions & References Stage 1: With copper(l) iodide, 1,10-Phenanthroline, potassium iodide in N,N-dimethyl-formamide, Time= 6h, T= 110 °C Stage 2: With N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide, Time= 60h, T= 110 °C Cristau, Henri-Jean; Ouali, Armelle; Spindler, Jean-Francis; Taillefer, Marc; Chemistry - A European Journal; vol. 11; nb. 8; (2005); p. 2483 - 2492

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View in Reaxys 99 % Chromat.

With N,N,N,N,-tetramethylethylenediamine, 1,5-bis-(diphenylphosphino)pentane, sodium carbonate, palladium diacetate in N,N-dimethyl acetamide, Time= 21h, T= 120 °C Sundermeier, Mark; Zapf, Alexander; Beller, Matthias; Angewandte Chemie - International Edition; vol. 42; nb. 14; (2003); p. 1661 - 1664 View in Reaxys N

K4[Fe(CN)6]

Rx-ID: 9846181 View in Reaxys 55/96 Yield 95 %

Conditions & References With sodium carbonate, palladium diacetate, Time= 16h, T= 140 °C Schareina, Thomas; Zapf, Alexander; Beller, Matthias; Journal of Organometallic Chemistry; vol. 689; nb. 24 SPEC. ISS.; (2004); p. 4576 - 4583 View in Reaxys

91 %

With sodium carbonate, potassium iodide, N,N`-dimethylethylenediamine, copper(II) bis(tetrafluoroborate) in N,N-dimethyl acetamide, Time= 16h, T= 140 °C Schareina, Thomas; Zapf, Alexander; Beller, Matthias; Tetrahedron Letters; vol. 46; nb. 15; (2005); p. 2585 - 2588 View in Reaxys

88 %

With sodium carbonate, palladium diacetate, Time= 16h, T= 120 °C Schareina, Thomas; Zapf, Alexander; Beller, Matthias; Chemical Communications; nb. 12; (2004); p. 1388 - 1389 View in Reaxys N

Rx-ID: 12700607 View in Reaxys 56/96 Yield

Conditions & References Reaction Steps: 3 1: 90 percent / acetone / Heating 2: (NH2OH)2*H2SO4; sodium acetate / ethanol / Heating 3: SOCl2 / benzene / Heating With thionyl chloride, hydroxyammonium sulfate, sodium acetate in ethanol, acetone, benzene Master, Hoshang E.; Khan, Shabana I.; Poojari, Krishna A.; Bioorganic and Medicinal Chemistry; vol. 13; nb. 16; (2005); p. 4891 - 4899 View in Reaxys Reaction Steps: 3 1: K2CO3 / acetone / Heating 2: hydroxylamine sulphate; sodium acetate / ethanol 3: SOCl2 / benzene / Heating With thionyl chloride, sodium acetate, potassium carbonate, hydroxylamine sulfate in ethanol, acetone, benzene Master, Hoshang E.; Khan, Shabana I.; Poojari, Krishna A.; Bioorganic and Medicinal Chemistry Letters; vol. 13; nb. 7; (2003); p. 1249 - 1251 View in Reaxys

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N O

O O

(S)-(Fmoc-amino)-(4-fluoro-phenyl)-acetic acid on Wang resin

Rx-ID: 12702212 View in Reaxys 57/96 Yield

Conditions & References Reaction Steps: 2 1: (NH2OH)2*H2SO4; sodium acetate / ethanol / Heating 2: SOCl2 / benzene / Heating With thionyl chloride, hydroxyammonium sulfate, sodium acetate in ethanol, benzene Master, Hoshang E.; Khan, Shabana I.; Poojari, Krishna A.; Bioorganic and Medicinal Chemistry; vol. 13; nb. 16; (2005); p. 4891 - 4899 View in Reaxys N

O N

Rx-ID: 1806143 View in Reaxys 58/96 Yield

Conditions & References With tri-tert-butyl phosphine, tributyltin chloride, tris(dibenzylideneacetone)dipalladium (0) in acetonitrile, Time= 17h, T= 80 °C

90 %

Yang, Chunhua; Williams, J. Michael; Organic Letters; vol. 6; nb. 17; (2004); p. 2837 - 2840 View in Reaxys With 18-crown-6 ether, tetrakis(triphenylphosphine) palladium(0) in benzene, Time= 50h, T= 80 °C , other temperature, Product distribution, Rate constant

81 %

Prochazka, Milos; Siroky, Miroslav; Collection of Czechoslovak Chemical Communications; vol. 48; nb. 6; (1983); p. 1765 1773 View in Reaxys N

O –C

N Zn 2+

Rx-ID: 11006951 View in Reaxys 59/96 Yield

Conditions & References

92 %

With palladium diacetate, triphenylphosphine on polystyrene in N,N-dimethyl-formamide, Time= 0.5h, T= 140 °C , Irradiation, microwave Srivastava, Rajiv R.; Collibee, Scott E.; Tetrahedron Letters; vol. 45; nb. 48; (2004); p. 8895 - 8897 View in Reaxys N

O –C

N Zn 2+

Rx-ID: 11006952 View in Reaxys 60/96 Yield 98 %

Conditions & References With palladium diacetate, triphenylphosphine on polystyrene in N,N-dimethyl-formamide, Time= 0.5h, T= 140 °C , Irradiation, microwave Srivastava, Rajiv R.; Collibee, Scott E.; Tetrahedron Letters; vol. 45; nb. 48; (2004); p. 8895 - 8897 View in Reaxys

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O N

Rx-ID: 2061012 View in Reaxys 61/96 Yield

Conditions & References With dibromobis(triphenylphosphine)nickel(II) in N,N,N,N,N,N-hexamethylphosphoric triamide, Time= 6h, T= 60 °C Sakakibara, Yasumasa; Okuda, Fumio; Shimobayashi, Akira; Kirini, Kunihiko; Sakai, Mutsuji; et al.; Bulletin of the Chemical Society of Japan; vol. 61; (1988); p. 1985 - 1990 View in Reaxys

82 % Chromat.

With N,N,N,N,-tetramethylethylenediamine, 1,5-bis-(diphenylphosphino)pentane, palladium diacetate in toluene, Time= 16h, T= 160 °C Sundermeier, Mark; Zapf, Alexander; Mutyala, Sateesh; Baumann, Wolfgang; Sans, Juergen; Weiss, Stefan; Beller, Matthias; Chemistry - A European Journal; vol. 9; nb. 8; (2003); p. 1828 - 1836 View in Reaxys N

Rx-ID: 9451649 View in Reaxys 62/96 Yield

Conditions & References

89 % Chromat.

With N,N,N,N,-tetramethylethylenediamine, trans-bromo(3-tolyl)bis(triphenylphosphine)palladium(II), 1,5-bis-(diphenylphosphino)pentane in toluene, T= 120 °C Sundermeier, Mark; Mutyala, Sateesh; Zapf, Alexander; Spannenberg, Anke; Beller, Matthias; Journal of Organometallic Chemistry; vol. 684; nb. 1-2; (2003); p. 50 - 55 View in Reaxys

N N

Rx-ID: 23992738 View in Reaxys 63/96 Yield 84%

Conditions & References 117 : 3-Methoxybenzonitrile Example 117 3-Methoxybenzonitrile A test tube was charged with CuI (20 mg, 0.10 mmol, 10 mol percent), 1,10-phenanthroline (36 mg, 0.20 mmol, 20 mol percent), Cs2CO3 (652 mg, 2.0 mmol), 3-iodobenzonitrile (229 mg, 1.0 mmol), methanol (162 μL, 4.0 mmol) and toluene (1 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 23 h. The resulting suspension was cooled to room temperature and filtered through a 0.5*1 cm pad of silica gel eluding with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2*20 cm; pentane/diethyl ether 5:1) provided 111 mg (84percent yield) of the title compound as a colorless oil. With CuI, caesium carbonate in methanol, toluene Patent; Buchwald, Stephen L.; Klapars, Artis; Antilla, Jon C.; Job, Gabriel E.; Wolter, Martina; Kwong, Fuk Y.; Nordmann, Gero; Hennessy, Edward J.; US2003/65187; (2003); (A1) English View in Reaxys

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O N

(v1)

Rx-ID: 9002446 View in Reaxys 64/96 Yield

Conditions & References

67 %

With 1-n-butyl-3-methylimidazolim bromide, Time= 24h, T= 90 °C Wu, Jeff Xin; Beck, Brandon; Ren, Rex X.; Tetrahedron Letters; vol. 43; nb. 3; (2002); p. 387 - 389 View in Reaxys N

HO N

Rx-ID: 9059777 View in Reaxys 65/96 Yield

Conditions & References

89 %

With copper(l) iodide, 1,10-Phenanthroline, caesium carbonate in toluene, Time= 23h, T= 110 °C Wolter, Martina; Nordmann, Gero; Job, Gabriel E; Buchwald, Stephen L; Organic letters; vol. 4; nb. 6; (2002); p. 973 - 976 View in Reaxys

O N

Rx-ID: 9190233 View in Reaxys 66/96 Yield

Conditions & References With dihydrogen peroxide, poly(bis-9,10-anthracenyl)diselenide in tert-butyl alcohol, Time= 1h, T= 55 °C

90 %

Giurg; Mlochowski; Ambrozak; Polish Journal of Chemistry; vol. 76; nb. 12; (2002); p. 1713 - 1720 View in Reaxys

O N

NH 2

N O

O O

Rx-ID: 9190234 View in Reaxys 67/96 Yield

Conditions & References

66 %, 19 %, With dihydrogen peroxide, sodium carbonate, acetonitrile, Time= 24h, T= 55 °C 10 % Giurg; Mlochowski; Ambrozak; Polish Journal of Chemistry; vol. 76; nb. 12; (2002); p. 1713 - 1720 View in Reaxys

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H N

N O

Rx-ID: 5294547 View in Reaxys 68/96 Yield

Conditions & References

89 %

With toluene-4-sulfonic acid in toluene, Time= 0.5h, Heating, Elimination Coskun, Necdet; Arikan, Nevin; Tetrahedron; vol. 55; nb. 40; (1999); p. 11943 - 11948 View in Reaxys N

H N

H 2N

O HO

Rx-ID: 16146158 View in Reaxys 69/96 Yield

Conditions & References Reaction Steps: 2 1: 87 percent / ethanol / 1 h / 20 °C 2: 89 percent / TsOH*H2O / toluene / 0.5 h / Heating With toluene-4-sulfonic acid in ethanol, toluene, 1: Condensation / 2: Elimination Coskun, Necdet; Arikan, Nevin; Tetrahedron; vol. 55; nb. 40; (1999); p. 11943 - 11948 View in Reaxys N

14C

O N

14C

(v1)

Rx-ID: 4821619 View in Reaxys 70/96 Yield

Conditions & References

1.024 g

in N,N-dimethyl-formamide, Time= 24h, T= 125 °C Ciszewska, Grazyna; Pfefferkorn, Heidi; Tang; Jones, Lawrence; Tarapata, Richard; Sunay, Ustun B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 651 - 668 View in Reaxys O

O O

Rx-ID: 4154071 View in Reaxys 71/96 Yield

Conditions & References

76 %

With tert.-butyl lithium in tetrahydrofuran, hexane, T= -94 °C Rutan, Kimberly J.; Heldrich, Frederick J.; Borges, Lawrence F.; Journal of Organic Chemistry; vol. 60; nb. 9; (1995); p. 2948 - 2950 View in Reaxys O O

P O

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O H N

O N H

Rx-ID: 3648862 View in Reaxys 72/96 Yield

Conditions & References

6 %, 59 %, 3 %, 2 %

With tris-(2-chloro-ethyl)-amine, sulfuric acid in chloroform, Time= 0.0833333h, T= 0 °C , Further byproducts given Sprecher, Milon; Kost, Daniel; Journal of the American Chemical Society; vol. 116; nb. 3; (1994); p. 1016 - 1026 View in Reaxys O

O P

O H N

NH 2

O O

Rx-ID: 3648863 View in Reaxys 73/96 Yield

Conditions & References

6 %, 59 %, 3 %, 8.5 %

O P

O O

H N

NH 2

H N

O O

Rx-ID: 3648864 View in Reaxys 74/96 Yield

Conditions & References

6 %, 3 %, 8.5 %, 0.8 %

O N O

O N

Rx-ID: 1746485 View in Reaxys 75/96

30/36

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Yield

Conditions & References

70 %, 22 %

With hydrogenchloride, hydroxylamine hydrochloride, Time= 2h, Heating Yamauchi; Chemical and Pharmaceutical Bulletin; vol. 41; nb. 11; (1993); p. 2042 - 2043 View in Reaxys N

O I

Rx-ID: 3887044 View in Reaxys 76/96 Yield

Conditions & References With sodium hydroxide in N,N-dimethyl acetamide, T= 65 °C , also in KF-cryptand 222 system, Rate constant Cork, David G.; Hayashi, Nobuyoshi; Journal of the Chemical Society, Chemical Communications; nb. 6; (1993); p. 527 - 529 View in Reaxys With sodium hydroxide in N,N-dimethyl acetamide, T= 25 °C , Rate constant Cork, David G.; Hayashi, Nobuyoshi; Bulletin of the Chemical Society of Japan; vol. 66; nb. 5; (1993); p. 1583 - 1585 View in Reaxys O (v3)

N N N

(v4)

Ru (v6)

(v4)

N O

(v4)

(v4) Ru (v6)

(v4)

Rx-ID: 26339831 View in Reaxys 77/96 Yield

Conditions & References With carbon monoxide in N,N-dimethyl acetamide, Kinetics, 1 atm CO bubbled for 30 s, 25°C; monitored by UV/VIS-spectrometry (at about 540-550 nm) Paulson, Donald R.; Bhakta, Sunil B.; Hyun, Rosemary Y.; Yuen, Marilyn; Beaird, Chyle E.; et al.; Inorganica Chimica Acta; vol. 151; (1988); p. 149 - 152 ; (from Gmelin) View in Reaxys

C–

N+

Rx-ID: 2286525 View in Reaxys 78/96 Yield 35 %, 21 %

Conditions & References in dimethyl sulfoxide, Time= 1h, T= 25 °C , Irradiation Petrillo, Giovanni; Novi, Marino; Garbarino, Giacomo; Dell'erba, Carlo; Tetrahedron; vol. 43; nb. 20; (1987); p. 4625 4634 View in Reaxys

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Rx-ID: 2831757 View in Reaxys 79/96 Yield

Conditions & References

35 %, 21 %

With tetra-n-butylammonium cyanide in dimethyl sulfoxide, Time= 1h, T= 25 °C , Irradiation Petrillo, Giovanni; Novi, Marino; Garbarino, Giacomo; Dell'erba, Carlo; Tetrahedron; vol. 43; nb. 20; (1987); p. 4625 4634 View in Reaxys N

NH 2

K2<Cu(CN)4*NH3>

Rx-ID: 7445026 View in Reaxys 80/96 Yield

Conditions & References With hydrogenchloride, sodium nitrite, 1.) water, poly(ethylene glycol), CH2Cl2, 0 deg C; 2.) poly(ethylene glycol), CH2Cl2, from 0 deg C to RT, Yield given. Multistep reaction. Yields of byproduct given Suzuki, Nobutaka; Azuma, Terukazu; Kaneko, Yoshihiro; Izawa, Yasuji; Tomioka, Hideo; Nomoto, Tateo; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1987); p. 645 - 648 View in Reaxys

NH 2

(v2)

N H

Rx-ID: 2412402 View in Reaxys 81/96 Yield

Conditions & References With hydrogenchloride, sodium nitrite, multistep reaction; diazotization and Sandmeyer reaction in polyethylene glycolCH2Cl2; 0 deg C to r.t. Suzuki, Nobutaka; Kaneko, Yoshihiro; Nomoto, Tateo; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 22; (1984); p. 1523 - 1524 View in Reaxys N

O N

(v1)

Rx-ID: 1806126 View in Reaxys 82/96 Yield 78 %

Conditions & References in N,N-dimethyl-formamide, T= 150 °C , other solvent, Product distribution, Rate constant Prochazka, Milos; Siroky, Miroslav; Collection of Czechoslovak Chemical Communications; vol. 48; nb. 6; (1983); p. 1765 1773 View in Reaxys

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Rx-ID: 1580736 View in Reaxys 83/96 Yield

Conditions & References

4 (unit not given), 49 (unit not given), 16 (unit not given)

Irradiation, further with acetone, Product distribution, Mechanism Soumillion, Jean Ph.; Wolf, Benoit De; Journal of the Chemical Society, Chemical Communications; nb. 9; (1981); p. 436 437 View in Reaxys

N O N

Rx-ID: 2936566 View in Reaxys 84/96 Yield

Conditions & References With polyethylene glycol in dichloromethane, Time= 1h, Irradiation, var. of reagent, time, Product distribution Suzuki, Nobutaka; Shimazu, Kazuo; Ito, Toshikuni; Izawa, Yasuji; Journal of the Chemical Society, Chemical Communications; nb. 24; (1980); p. 1253 - 1255 View in Reaxys N O

O N

Rx-ID: 4121330 View in Reaxys 85/96 Yield

Conditions & References in water, acetone, tert-butyl alcohol, Irradiation Den Heijer,J. et al.; Tetrahedron; vol. 33; (1977); p. 779 - 786 View in Reaxys O

O H 2N

O HO

S O

Rx-ID: 624659 View in Reaxys 86/96 Yield

Conditions & References With phosphorus pentachloride, T= 200 °C Miller; ; vol. Vol. III; (1955); p. 646,648 View in Reaxys

N O

Rx-ID: 20496 View in Reaxys 87/96

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Yield

Conditions & References Hauser; Vermillion; Journal of the American Chemical Society; vol. 63; (1941); p. 1224,1226 View in Reaxys O

N Cl

Rx-ID: 60816 View in Reaxys 88/96 Yield

Conditions & References T= 0 °C , Geschwindigkeit Hauser; Le Maistre; Rainsford; Journal of the American Chemical Society; vol. 57; (1935); p. 1056,1058 View in Reaxys O

N O

N Cl

Rx-ID: 455447 View in Reaxys 89/96 Yield

Conditions & References T= 177 °C , spontane Zersetzung Hauser; Gillaspie; Le Maistre; Journal of the American Chemical Society; vol. 57; (1935); p. 567 View in Reaxys

O–

Na +

O N

N O

Rx-ID: 850680 View in Reaxys 90/96 Yield

Conditions & References T= 0 °C , Behandeln des Reaktionsprodukts mit Phosphorpentachlorid in Chloroform bei 0grad Jones; ; vol. 45; p. 38; ; vol. 29; (1935); p. 4341; Chem. Zentralbl.; vol. 105; nb. II; (1934); p. 3259 View in Reaxys

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N O

3-methoxy-benzaldehyde chloroimine

Rx-ID: 7174475 View in Reaxys 91/96 Yield

Conditions & References With sodium hydroxide Hauser; Le Maistre; Rainsford; Journal of the American Chemical Society; vol. 57; (1935); p. 1056,1058 View in Reaxys

O–

Na +

N O O

O N

Rx-ID: 850401 View in Reaxys 92/96 Yield

Conditions & References T= 0 °C , Behandeln des Reaktionsprodukts in Chloroform mit POCl5 und anschliessend mit Eis Jones; ; vol. 45; (1934); p. 38,40 View in Reaxys

NH 2

N O

Rx-ID: 332626 View in Reaxys 93/96 Yield

Conditions & References Bailar; Journal of the American Chemical Society; vol. 52; (1930); p. 3596,3597 View in Reaxys

Rx-ID: 22106119 View in Reaxys 94/96

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Yield

Conditions & References Reaction Steps: 2 1: aqueous ammonia With ammonium hydroxide Bailar; Journal of the American Chemical Society; vol. 52; (1930); p. 3596,3597 View in Reaxys N O

N+

copper (I)-cyanide

Rx-ID: 7174476 View in Reaxys 95/96 Yield

Conditions & References Carothers; Bickford; Hurwitz; Journal of the American Chemical Society; vol. 49; (1927); p. 2908 View in Reaxys

O N Cl

natrium carbonate

N O

3-methoxy-benzaldoxime acetate

Rx-ID: 8249528 View in Reaxys 96/96 Yield

Conditions & References aufeinanderfolgende Einw. von Acetanhydrid und Sodaloesung Brady; Dunn; Journal of the Chemical Society; vol. 105; (1914); p. 2416 View in Reaxys

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