1,2,3-Trimethoxy-5-(2-nitrovinyl)benzene

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17 reactions in Reaxys

2017-11-16 00h:20m:58s (EST)

NO 2

O O

Search as: As drawn

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O O

N

O

E

O O

O

O N O

Rx-ID: 590449 View in Reaxys 1/17 Yield 92 %

Conditions & References With ammonium acetate in acetic acid, Time= 3h, T= 20 °C , Irradiation Sathish, Manda; Chetna, Jadala; Hari Krishna, Namballa; Shankaraiah, Nagula; Alarifi, Abdullah; Kamal, Ahmed; Journal of Organic Chemistry; vol. 81; nb. 5; (2016); p. 2159 - 2165 View in Reaxys

85 %

General procedure for the synthesis of β-nitrostyrenes General procedure: A mixture of catalyst (50 mg) and piperidine (0.1 mmol, 10 μL) in dry toluene (1mL) was placed in a microwave tube having a magnetic stirrer. Subsequently, aromatic aldehyde (1 mmol) and nitromethane (1.5 mmol) were added to the mixture, which was heated under microwave irradiation (30 W, 110 °C) during 30 minutes. Then, catalyst was removed by centrifugation and washed with CH2Cl2 (5x5mL). The combined organic extracts were evaporated, giving the corresponding β-nitrostyrene, which was purified by column chromatography (CH2Cl2 or hexanes-EtOAc 1:1) and recrystallization (CH2Cl2-hexanes, 1:2). With piperidine in toluene, Time= 0.5h, T= 110 °C , Microwave irradiation Vergara-Arenas, Blanca Ivonne; Lomas-Romero, Leticia; Ángeles-Beltrán, Deyanira; Negrón-Silva, Guillermo Enrique; Gutiérrez-Carrillo, Atilano; Lara, Víctor Hugo; Morales-Serna, José Antonio; Tetrahedron Letters; vol. 58; nb. 28; (2017); p. 2690 - 2694 View in Reaxys

84 %

With acetic acid, N-butylamine, Time= 1h, Heating Fierro; Rezende; Sepulveda-Boza; Reyes-Parada; Cassels; Journal of Chemical Research - Part S; nb. 7; (2001); p. 294 - 296 View in Reaxys

82 %

With piperidine, iron(III) chloride in toluene, Time= 5h, Reflux, Henry Nitro Aldol Condensation Jalal, Swapnadeep; Sarkar, Soumen; Bera, Krishnendu; Maiti, Sukhendu; Jana, Umasish; European Journal of Organic Chemistry; nb. 22; (2013); p. 4823 - 4828 View in Reaxys

75 %

With piperidine in toluene, Time= 0.5h, T= 110 °C , Microwave irradiation, Henry Nitro Aldol Condensation, Reagent/ catalyst González-Olvera; Vergara-Arenas; Negrón-Silva; Angeles-Beltrán; Lomas-Romero; Gutiérrez-Carrillo; Lara; Morales-Serna; RSC Advances; vol. 5; nb. 120; (2015); p. 99188 - 99192 View in Reaxys Seebach,D. et al.; Chemische Berichte; vol. 108; (1975); p. 1924 - 1945 View in Reaxys Dore,J.-C. et al.; Chimica Therapeutica; vol. 6; (1971); p. 167 - 185 View in Reaxys Slotta; Szyszka; Journal fuer Praktische Chemie (Leipzig); vol. <2> 137; (1933); p. 339,349 View in Reaxys With ammonium acetate in acetic acid, T= 70 °C , Knoevenagel condensation Liu, Ju-Tsung; Yao, Ching-Fa; Tetrahedron Letters; vol. 42; nb. 35; (2001); p. 6147 - 6150 View in Reaxys With ethylenediamine diacetic acid, Time= 3h, T= 22 °C , sonification, Henry condensation reaction Kaap, Sylvia; Quentin, Iris; Tamiru, Dereje; Shaheen, Mohammed; Eger, Kurt; Steinfelder, Hans Juergen; Biochemical Pharmacology; vol. 65; nb. 4; (2003); p. 603 - 610 View in Reaxys

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With aminopropyl-functionalized mesoporous silica spheres, Time= 1h, T= 89.84 °C , Product distribution, Further Variations: Catalysts Suzuki, Tomiko M.; Yamamoto, Masami; Fukumoto, Keiko; Akimoto, Yusuke; Yano, Kazuhisa; Journal of Catalysis; vol. 251; nb. 2; (2007); p. 249 - 257 View in Reaxys With ammonium acetate, acetic acid, T= 22 - 25 °C , Sonication, Henry reaction Pettit, Robin K.; Pettit, George R.; Hamel, Ernest; Hogan, Fiona; Moser, Bryan R.; Wolf, Sonja; Pon, Sandy; Chapuis, Jean-Charles; Schmidt, Jean M.; Bioorganic and Medicinal Chemistry; vol. 17; nb. 18; (2009); p. 6606 6612 View in Reaxys With ethanolamine supported on SiO2 Puerto Galvis, Carlos E.; Kouznetsov, Vladimir V.; Organic and Biomolecular Chemistry; vol. 11; nb. 42; (2013); p. 7372 - 7386 View in Reaxys Stage 1: With sodium hydroxide, Cooling with ice Stage 2: With hydrogenchloride in water, Cooling with ice Guo, Shuhui; Mi, Xueling; Tetrahedron Letters; vol. 58; nb. 30; (2017); p. 2881 - 2884 View in Reaxys

O O

N

O

O N

O O

O

Rx-ID: 590450 View in Reaxys 2/17 Yield 94 %

Conditions & References General procedure: (a) Microwave: a mixture of aryl aldehyde (1 mmol) and nitromethane (3 mL) was introduced into a glass microwave tube (tube of 4 mL); a catalytic amount of ammonium acetate (0.3 mmol) was added and the tube was introduced into the microwave system (CEM-Discover) and initially irradiated at 250 W and 90 °C for 25 min. The reaction mixture was then cooled and the nitromethane was evaporated in a Buechi microdistillation apparatus. The nitrostyrenes were purified by silica-gel column chromatography, and eluted with a mixture of hexane and ethyl acetate. With ammonium acetate, Time= 0.416667h, T= 90 °C , Microwave irradiation, Henry reaction Rodriguez, Jose M.; Dolors Pujol; Tetrahedron Letters; vol. 52; nb. 21; (2011); p. 2629 - 2632 View in Reaxys

91 %

6.2.1. 1-(Benzyloxy)-2-methoxy-4-(2-nitroethenyl)benzene (12a) General procedure: To a solution of 10a (8.5 g, 35 mmol) in glacial acetic acid (30 mL) was added CH3NO2 (6.4 g, 105 mmol) and ammonium acetate (2.70 g, 35 mmol), the mixture was heated to 90 °C for 4 h, then cooled to room temperature and poured to water (200 mL) to favor the precipitation as a solid, which was subsequently filtered and washed with cold water and methanol. The crude product was purified by column chromatography (PE/EA = 6/1) to yield 12a (8.58 g, 86percent) as a yellow solid. With ammonium acetate, acetic acid, Time= 4h, T= 90 °C Qian, Wangke; Lu, Weijian; Sun, Haifeng; Li, Zeng; Zhu, Liyuan; Zhao, Rui; Zhang, Lei; Zhou, Shengbin; Zhou, Yu; Jiang, Hualiang; Zhen, Xuechu; Liu, Hong; Bioorganic and Medicinal Chemistry; vol. 20; nb. 15; (2012); p. 4862 - 4871 View in Reaxys

83 %

With potassium fluoride, N,N-dimethylammonium chloride in toluene, Time= 5h, Heating Dauzonne; Royer; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 4; (1986); p. 1628 - 1633 View in Reaxys

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73.8 %

With ammonium acetate, acetic acid, Time= 3h, Reflux Zheng, Can-Hui; Chen, Jun; Liu, Jia; Zhou, Xiao-Tian; Liu, Na; Shi, Duo; Huang, Jing-Jing; Lv, Jia-Guo; Zhu, Ju; Zhou, You-Jun; Archiv der Pharmazie; vol. 345; nb. 6; (2012); p. 454 - 462 View in Reaxys With potassium hydroxide, ethanol, T= -5 °C , Behandeln des Reaktionsprodukts mit verd. Salzsaeure Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 92; (1915); p. 200 View in Reaxys Spaeth; Monatshefte fuer Chemie; vol. 40; (1919); p. 138; Monatshefte fuer Chemie; vol. 42; (1921); p. 263 View in Reaxys Time= 0.5h, Heating Bobowski; West; Omecinsky; Journal of Heterocyclic Chemistry; vol. 29; nb. 1; (1992); p. 33 - 49 View in Reaxys With ammonium acetate, acetic acid, Henry-reaction Silveira, Claudio C.; Bernardi, Carmem R.; Braga, Antonio L.; Kaufman, Teodoro S.; Tetrahedron Letters; vol. 40; nb. 27; (1999); p. 4969 - 4972 View in Reaxys With ammonium acetate, acetic acid Vaccari, Daniele; Davoli, Paolo; Ori, Claudia; Spaggiari, Alberto; Prati, Fabio; Synlett; nb. 18; (2008); p. 2807 2810 View in Reaxys With methylamine in methanol, Time= 4h Wang, Yan-Xiang; Wang, Yu-Ping; Zhang, Hao; Kong, Wei-Jia; Li, Ying-Hong; Liu, Fei; Gao, Rong-Mei; Liu, Ting; Jiang, Jian-Dong; Song, Dan-Qing; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 21; (2009); p. 6004 - 6008 View in Reaxys 4.1.1. General procedure 1 for the synthesis of 2-aryl-1-nitroethenes 2 and 3 General procedure: To a solution of the corresponding arylaldehyde in toluene were added nitromethane (11 equivalents), dimethylamine hydrochloride (4 equivalents) and potassium fluoride (0.15 equivalents). The flask was equipped with a Dean-Stark and the mixture was heated at reflux temperature until the disappearance of the arylaldehyde (usually noted after a reaction time of 4-5 h). After being cooled at room temperature, the reaction mixture was evaporated under vacuum to eliminate the toluene, then diluted with water and extracted by CH2Cl2 (3.x.). In some cases, a filtration over Celite surface was required in order to eliminate excess reagent or reaction residues prior to extraction. The organic phase was then washed with water, dried over MgSO4, filtered and concentrated under vacuum. Crude product was purified by chromatography on silica gel in order to afford the desired compound. With potassium fluoride, N,N-dimethylammonium chloride in toluene, Reflux Mur Blanch, Nuria; Chabot, Guy G.; Quentin, Lionel; Scherman, Daniel; Bourg, Stephane; Dauzonne, Daniel; European Journal of Medicinal Chemistry; vol. 54; (2012); p. 22 - 32 View in Reaxys With sodium hydroxide in methanol, water, T= 15 °C , Inert atmosphere Keene, Craig; Kuerti, Laszlo; Synthesis (Germany); vol. 45; nb. 13; (2013); p. 1719 - 1729; Art.No: SS-2013C0260-FA View in Reaxys With acetic acid, N-butylamine, Time= 4h, Reflux Rahmani-Nezhad, Samira; Safavi, Maliheh; Pordeli, Mahboobeh; Ardestani, Sussan Kabudanian; Khosravani, Leila; Pourshojaei, Yaghoub; Mahdavi, Mohammad; Emami, Saeed; Foroumadi, Alireza; Shafiee, Abbas; European Journal of Medicinal Chemistry; vol. 86; (2014); p. 562 - 569 View in Reaxys

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With sodium hydroxide in methanol, Time= 0.25h, Cooling with ice Balachandra, Biguvu; Shanmugam, Sivakumar; Muneeswaran, Thillaichidambaram; Ramakritinan, Muthiah; RSC Advances; vol. 5; nb. 79; (2015); p. 64781 - 64789 View in Reaxys With zirconium(IV) chloride, Time= 3h, T= 0 - 20 °C Sridhar, Gattu; Somnath, Mudavath; Sharma, Gangavaram V. M.; Prashanth, Thodupunuri; Synthetic Communications; vol. 47; nb. 6; (2017); p. 551 - 556 View in Reaxys

O

O O

O

E

O N

O

OH

O

Rx-ID: 45328053 View in Reaxys 3/17 Yield

Conditions & References

80 %

Typical Procedure General procedure: The mixture of α,β-Unsaturated Acids (0.5 mmol), Fe(NO3)3 (1.0 mmol), Pyridine (0.5 mmol) and toluene (2 ml) was stirred at 100 °C for 12 h. After cooling to r.t., the reaction mixture was washed with H2O (10 ml), and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. The mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (EA/nHexane=15percent) to afford pure product. With pyridine, Iron(III) nitrate nonahydrate in toluene, Time= 12h, T= 100 °C Yang, Zan; Li, Jiao; Hua, Jie; Yang, Tao; Yi, Jianmin; Zhou, Congshan; Synlett; vol. 28; nb. 9; (2017); p. 1079 1082; Art.No: ST-2016-W0789-L View in Reaxys

O O

O

E O

O OH

O

E O

O N O

Rx-ID: 10121451 View in Reaxys 4/17 Yield 93 %

Conditions & References General procedure for synthesis of (E)-nitroolefins 3a–l General procedure: A 25-mL Schlenk tube was charged with α,β-unsaturated acid (0.4 mmol), Cu(NO3)2 (0.48 mmol), and CH3CN (2 mL). The tube was sealed, then the mixture was stirred under air at 110 °C for 8 h. After completion of the reaction as monitored by thin-layer chromatography (TLC), H2O (5 mL) was added. The mixture was extracted with dichloromethane (3 X 4 mL). The combined organic layers were washed with saturated sodium bicarbonate solution (10 mL) and water (10 mL), dried over anhydrous Na2SO4, then concentrated by rotary evaporator. Finally, the residue was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 6:1) to provide the desired products (3). (E)-(2-Nitrovinyl)benzene (3a) [18, 19, 21] With copper(II) nitrate in acetonitrile, Time= 8h, T= 110 °C , Sealed tube, Green chemistry, regioselective reaction Luo, Zai-Gang; Xu, Feng; Fang, Yu-Yu; Liu, Peng; Xu, Xue-Mei; Feng, Cheng-Tao; Li, Zhong; He, Jie; Research on Chemical Intermediates; vol. 42; nb. 6; (2016); p. 6079 - 6087 View in Reaxys

80 %

With 2,2'-azobis(isobutyronitrile), nitric acid in acetonitrile, Time= 2h, T= 35 °C , nitro-Hunsdiecker reaction Das, Jaya Prakash; Sinha, Pradipta; Roy, Sujit; Organic Letters; vol. 4; nb. 18; (2002); p. 3055 - 3058 View in Reaxys

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80 %

With tert.-butylnitrite, 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical in acetonitrile, Time= 3h, T= 50 °C , stereoselective reaction Manna, Srimanta; Jana, Sandipan; Saboo, Tapish; Maji, Arun; Maiti, Debabrata; Chemical Communications; vol. 49; nb. 46; (2013); p. 5286 - 5288 View in Reaxys

75 %

With ammonium cerium(IV) nitrate in acetonitrile, Time= 1.5h, T= 20 °C Sridhar Rao; Srinivas; Suresh Babu; Madhusudana Rao; Tetrahedron Letters; vol. 46; nb. 47; (2005); p. 8141 8143 View in Reaxys

O O

O

N trans trans O trans trans O

O

E

O O

N

O

Rx-ID: 41278125 View in Reaxys 5/17 Yield

Conditions & References

88 %

General procedure for De oxygenation of aliphatic and aromatic epoxide, chalcone epoxide, nitro styrene epoxide and nitrochromene epoxide by novel SnCl 2 / NaI reagent: General procedure: To a solution epoxide (1mmol) and NaI (3mmol) in absolute alcohol (5ml), SnCl2 (2mmol) was added in a several portions. The mixture was stirred at reflux temperature and the progress of reaction was monitored by TLC. Within 2-10 min the reaction mixture is poured in ice-water, precipitation obtained, stirred for 10 min and filtered the solid, dried to obtained pure products 2a-12a/ 1b-17b/1c-10c and 1d- 10d with 85-96percent yield. With sodium iodide, tin(ll) chloride in ethanol, Time= 0.116667h, Reflux, Green chemistry Pathe, Gulab Khushalrao; Ahmed, Naseem; Synthesis (Germany); vol. 47; nb. 22; (2015); p. 3542 - 3552; Art.No: SS-2015-Z0312-OP View in Reaxys

O

O OH

O

E

N O

O

O N O

Rx-ID: 9724591 View in Reaxys 6/17 Yield 68 %

Conditions & References General Procedure for Dehydration of 2-Nitroalcohols 4 General procedure: A heterogeneous mixture of 2-nitroalcohol (4, 1.2 mmol) and deionized water (2mL) at 5–10 °C, was treated portionwise with powdered K2CO3 (0.18 g, 1.3 mmol). The mixture was stirred at 5–10 °C until it turned homogeneous. The reaction mixture (at 5–10 °C) was acidified with 2N HCl to pH 6 and extracted with ether. The extracts were washed with NaHSO3 solution and water to remove traces of aldehyde (deriving from a competing retro-Henry reaction). Removal of the solvent in vacuo furnished the corresponding (E)-nitroalkene (6), found to be homogeneousby thin-layer chromatography (TLC) and characterized spectroscopically. Stage 1: With potassium carbonate in water, Time= 0.5h, Green chemistry Stage 2: With hydrogenchloride in water, pH= 6, Green chemistry Chandrasekhar, Sosale; Shrinidhi, Annadka; Synthetic Communications; vol. 44; nb. 20; (2014); p. 3008 - 3018 View in Reaxys With methanesulfonyl chloride, triethylamine in dichloromethane, T= 0 - 20 °C Taylor, Edward C.; Liu, Bin; Journal of Organic Chemistry; vol. 68; nb. 26; (2003); p. 9938 - 9947 View in Reaxys

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O

E

O

N

O

Rx-ID: 38693596 View in Reaxys 7/17 Yield

Conditions & References

92 %

[(E)-2-Nitrovinyl]benzene (2a); Typical Procedure General procedure: A mixture of styrene (0.104 g, 1.0 mmol), Claycop [0.605 g, 1.5 mmol containing 1.5 equiv Cu(NO3)2], TEMPO (0.0156 g, 20 molpercent), and 1,4-dioxane (5 mL) was stirred at 80 °C for 1 h. The mixture was then cooled to r.t., and the Claycop was collected by filtration and washed with 1,4-dioxane (3 × 5 mL). The organic phases were combined and concentrated under vacuum. The crude product was purified by recrystallization or column chromatography (EtOAc–hexanes) to give a crystalline yellow solid With 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical in 1,4-dioxane, Time= 1h, T= 80 °C , Green chemistry, stereoselective reaction Begari, Eeshwaraiah; Singh, Chandani; Nookaraju; Kumar, Pradeep; Synlett; vol. 25; nb. 14; (2014); p. 1997 2000; Art.No: ST-2014-D0206-L View in Reaxys

O O

N

O

O OH

O

N

O O

O

N O

O

Rx-ID: 30744538 View in Reaxys 8/17 Yield

Conditions & References

18 %, 18 %

General procedure: (b) Ultrasound: a mixture of aryl aldehyde (1 mmol) and nitromethane (3 mL) was introduced into a glass microwave tube; a catalytic amount of ammonium acetate (0.2 mmol) was added and the tube was placed inside an ultrasound apparatus (Ultrasounds Medi II, Selecta, Spain) preheated at 60 °C. It was exposed for 45 min at 100 W and 18 kHz. The reaction mixture was then cooled and the nitromethane was evaporated on a Buechi microdistillation apparatus. The compounds obtained after isolation and purification showed analytical data in accordance with the assigned structures. With ammonium acetate, Time= 0.75h, T= 60 °C , Ultrasound irradiation, Henry reaction Rodriguez, Jose M.; Dolors Pujol; Tetrahedron Letters; vol. 52; nb. 21; (2011); p. 2629 - 2632 View in Reaxys

O

E

O O

O

O N O

Rx-ID: 13389016 View in Reaxys 9/17 Yield 41%

Conditions & References 9 : Synthesis of (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenoic acid amide hydrochloride EXAMPLE 9 Synthesis of (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenoic acid amide hydrochloride A mixture of 3,4,5-trimethoxybenzaldehyde (9.80 g, 50 mmol), nitromethane (18 ml), ammonium acetate (4.11 g) and acetic acid (38 ml) was heated and refluxed for 2 hours. After the reaction mixture was concentrated under reduced pressure, 10percent aqueous sodium hydroxide solution was added to the residue and the reaction mixture was extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate.

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The solvent was distilled out under reduced pressure and the residue was purified by silica gel chromatography (dichloromethane) and recrystallized to yield trans-3,4,5-trimethoxy-β-nitrostyrene (4.96 g, 41percent). Properties: mp 116-118° C. (ethanol) 1H-NMR (CDCl ) δ: 3.91 (6H, s), 3.92 (3H, s), 6.77 (2H, s), 7.54 (1H, d, J=13.6 Hz), 7.94 (1H, d, J=13.6 Hz) 3 With ammonium acetate, sodium hydroxide, acetic acid in nitromethane Patent; Tsumura and Co.; US6313153; (2001); (B1) English View in Reaxys Reaction Steps: 2 1: aq. NaOH / ethanol / 65 h / 38 °C 2: CH3SO2Cl; Et3N / CH2Cl2 / 0 - 20 °C With sodium hydroxide, methanesulfonyl chloride, triethylamine in ethanol, dichloromethane, 1: Henry reaction Taylor, Edward C.; Liu, Bin; Journal of Organic Chemistry; vol. 68; nb. 26; (2003); p. 9938 - 9947 View in Reaxys 4.96 g (41%)

P.3 : Synthesis of (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenamide hydrochloride (compound 9) Preparation example 3 Synthesis of (E)-N-methyl-3-(3-pyridyl)-N-(3,4,5-trimethoxyphenethyl)-2-propenamide hydrochloride (compound 9) A mixture of 9.80 g (50 mmol) of 3,4,5-trimethoxybenzaldehyde, 18 mL of nitromethane, 4.11 g of ammonium acetate and 38 mL of acetic acid was heated under reflux for 2 hours. After concentrating the reaction solution under vacuum, 10percent aqueous sodium hydroxide was added to the residue, and the residue was then extracted using dichloromethane, washed with water, and then dried over anhydrous magnesium sulfate. After removing the solvent by vacuum evaporation, the residue was purified by silica gel column chromatography (dichloromethane) and recrystallized to obtain 4.96 g (41percent) of trans-3,4,5-trimethoxy-β-nitrostyrene. Property: mp 116-118°C (ethanol) 1H-NMR (CDCl )δ: 3.91 (6H, s), 3.92 (3H, s), 6.77 (2H, s), 7.54 (1H, d, J=13.6Hz), 7.94 (1H, d, J= 13.6Hz) 3 With ammonium acetate, aqueous sodium hydroxide, acetic acid in nitromethane, dichloromethane Patent; TSUMURA and CO.; EP1495757; (2005); (A1) English View in Reaxys

O

O O

HO

N

O

HN O

O N

H

O N O

O

O O

O

Rx-ID: 9059751 View in Reaxys 10/17 Yield

Conditions & References Stage 1: With water, silica gel Stage 2: in dichloromethane Bourry, Anne; Pitard, Franck; Rigo, Benoit; Sanz, Gerard; Camus, Fabrice; Norberg, Bernadette; Durant, Francois; Couturier, Daniel; Journal of Heterocyclic Chemistry; vol. 39; nb. 1; (2002); p. 109 - 118 View in Reaxys

O

O N

O O

O

Rx-ID: 14882124 View in Reaxys 11/17

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Yield

Conditions & References Reaction Steps: 3 1.1: 100 percent / potassium tert-butoxide / 4.5 h / 100 °C 2.1: 73 percent / triflic acid / CH2Cl2 / 4 h 3.1: silica; H2O 3.2: CH2Cl2 With trifluorormethanesulfonic acid, potassium tert-butylate, water, silica gel in dichloromethane Bourry, Anne; Pitard, Franck; Rigo, Benoit; Sanz, Gerard; Camus, Fabrice; Norberg, Bernadette; Durant, Francois; Couturier, Daniel; Journal of Heterocyclic Chemistry; vol. 39; nb. 1; (2002); p. 109 - 118 View in Reaxys Reaction Steps: 2 1: KOH / ethanol 2: CH2Cl2 / -12 °C With potassium hydroxide in ethanol, dichloromethane Aranda,G.; Chimica Therapeutica; vol. 6; (1971); p. 262 - 267 View in Reaxys

O

O N Si

O

Si

N O

O

Rx-ID: 14911374 View in Reaxys 12/17 Yield

Conditions & References Reaction Steps: 2 1.1: 73 percent / triflic acid / CH2Cl2 / 4 h 2.1: silica; H2O 2.2: CH2Cl2 With trifluorormethanesulfonic acid, water, silica gel in dichloromethane Bourry, Anne; Pitard, Franck; Rigo, Benoit; Sanz, Gerard; Camus, Fabrice; Norberg, Bernadette; Durant, Francois; Couturier, Daniel; Journal of Heterocyclic Chemistry; vol. 39; nb. 1; (2002); p. 109 - 118 View in Reaxys

O

O OH

O

N O

O

Rx-ID: 1114654 View in Reaxys 13/17 Yield

Conditions & References in dichloromethane, T= -12 °C Aranda,G.; Chimica Therapeutica; vol. 6; (1971); p. 262 - 267 View in Reaxys

O O

O N O

O

Rx-ID: 7677150 View in Reaxys 14/17

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Yield

Conditions & References 3,4,5-Trimethoxy-benzaldehyd, Nitromethan (als Zwischenprodukt nicht isoliert) Franck; Blaschke; Justus Liebigs Annalen der Chemie; vol. 695; (1966); p. 144,154 View in Reaxys

O O

N

O

OH

O

alcoholic KOH-solution

O

O N

O O

O

Rx-ID: 5520144 View in Reaxys 15/17 Yield

Conditions & References Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 92; (1915); p. 200 View in Reaxys Spaeth; Monatshefte fuer Chemie; vol. 40; (1919); p. 138; Monatshefte fuer Chemie; vol. 42; (1921); p. 263 View in Reaxys

O O

N

O

OH

O

methanolic KOH-solution

O

O N

O O

O

Rx-ID: 5520145 View in Reaxys 16/17 Yield

Conditions & References Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 92; (1915); p. 200 View in Reaxys Spaeth; Monatshefte fuer Chemie; vol. 40; (1919); p. 138; Monatshefte fuer Chemie; vol. 42; (1921); p. 263 View in Reaxys

O

O O

O

O N

Cl O

O

Rx-ID: 22021281 View in Reaxys 17/17 Yield

Conditions & References Reaction Steps: 2 1: toluene; hydrogen; palladium-barium sulfate 2: alcohol; KOH-solution / -5 °C / Behandeln des Reaktionsprodukts mit verd. Salzsaeure With potassium hydroxide, Pd-BaSO4, ethanol, hydrogen, toluene Spaeth; Monatshefte fuer Chemie; vol. 40; (1919); p. 138; Monatshefte fuer Chemie; vol. 42; (1921); p. 263 View in Reaxys

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