Reactions (210)
Yield
Substances (373)
Citations (138)
Conditions
References
199
Synthesize Find similar With iron; acetic acid in methanol; water
Heating;
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Rx-ID: 27987792
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Yeates, Clive L.; Batchelor, John F.; Capon, Edward C.; Cheesman, Neil J.; Fry, Mitch; Hudson, Alan T.; Pudney, Mary; Trimming, Helen; Woolven, James; Bueno, Jose M.; Chicharro, Jesus; Fernandez, Esther; Fiandor, Jose M.; Gargallo-Viola, Domingo; De Las Heras, Federico Gomez; Herreros, Esperanza; Leon, Maria L.
Journal of Medicinal Chemistry, 2008 , vol. 51, # 9 p. 2845 - 2852 Title/Abstract Full Text View citing articles Show Details
200
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Rx-ID: 3258104
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52%
With iron; acetic acid
0.5 h; Heating;
Sargent, Thornton; Shulgin, Alexander T.; Mathis, Chester A.
Journal of Medicinal Chemistry, 1984 , vol. 27, # 8 p. 1071 - 1077 Title/Abstract Full Text View citing articles Show Details
201
Synthesize Find similar With tri-n-butyl-tin hydride; ozone
1) methylene chloride, 24h, roomtemp., 2) -78 deg C up to room temp.; Yield given. Multistep reaction;
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Rx-ID: 2237152
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Palomo, Claudio; Aizpurua, Jesus M.; Cossio, Fernando P.; Garcia, Jesus M.; Lopez, M. Concepcion; Oiarbide, Mikel
Journal of Organic Chemistry, 1990 , vol. 55, # 7 p. 2070 - 2078 Title/Abstract Full Text View citing articles Show Details
202
Synthesize Find similar Multi-step reaction with 2 steps 1: 1) tributyltin hydride, 2) ozone / 1) methylene chloride, 24h, roomtemp., 2) -78 deg C up to room temp. 2: 70 percent / thiourea, triethylamine / methanol / 0.67 h / Ambient temperature View Scheme
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Rx-ID: 21917241
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Palomo, Claudio; Aizpurua, Jesus M.; Cossio, Fernando P.; Garcia, Jesus M.; Lopez, M. Concepcion; Oiarbide, Mikel
Journal of Organic Chemistry, 1990 , vol. 55, # 7 p. 2070 - 2078 Title/Abstract Full Text View citing articles Show Details
203
Synthesize Find similar With tri-n-butyl-tin hydride; ozone
1) methylene chloride, 24h, roomtemp., 2)
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Rx-ID: 2239758
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Palomo, Claudio; Aizpurua, Jesus M.; Cossio, Fernando P.; Garcia, Jesus M.; Lopez, M. Concepcion; Oiarbide, Mikel
Journal of Organic Chemistry, 1990 , vol. 55, # 7 p. 2070 - 2078
-78 deg C up to room temp.; Yield given. Multistep reaction;
Title/Abstract Full Text View citing articles Show Details
204
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83%
With hydrogenchloride; anhydrous iron chloride; iron in ethanol; water
5 h; Reflux; Hide Experimental Procedure
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Rx-ID: 37966378
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Llabres, Salome; Garcia-Rates, Sara; Cristobal-Lecina, Edgar; Riera, Antoni; Borrell, Jose Ignacio; Camarasa, Jorge; Pubill, David; Luque, F. Javier; Escubedo, Elena
European Journal of Medicinal Chemistry, 2014 , vol. 81, p. 35 - 46 Title/Abstract Full Text View citing articles Show Details
4.1.2. 1-(3,4-bis(benzyloxy)phenyl)propan-2-one (3)
In a 3 necked round bottomed flask, nitro compound 2 (1.24 g,3.31 mmol), Fe powder (1.11 g, 19.9 mmol, 6 equiv) and FeCl3 (0.12 mg, 0.76 mmol) were suspended in ethanol (15 mL). To this mixture water (30 mL) and conc HCl (2 mL) were added and the solution was heated at reflux during 5 h. The reaction was cooled down and the pH adjusted to 8 with 40percent NH4OH solution, filteredthrough celite and extracted with EtOAc. The organic phase was washed with water, dried with MgSO4 and evaporated to give abrown crude, which was purified by column chromatography (SiO2/hexanes/ethyl acetate) to afford 3 (0.95 g, 83percent yield) as brown oil.
205
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With hydrogenchloride; anhydrous iron chloride; water; iron
T=60 - 90°C; 2.5 h; Hide Experimental Procedure
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Rx-ID: 33148528
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ZENTIVA, K.S.; VLASAKOVA, Ruzena; HAJICEK, Josef; SLAVIKOVA, Marketa
Patent: WO2012/62229 A1, 2012 ; Location in patent: Page/Page column 24; 27 ; Title/Abstract Full Text Show Details
7; 12:
Example 7Preparation of l-[3-(benzyloxy)propyl]-5-(2-oxopropyl)indoline-7-carbonitrile (general formula VII: Bn = PhCH2); 3.45 g (9.1 mmol) of l-[3-(benzyloxy)propyl]-5-(2-nitroprop-l-en-l-yl)indoline-7-carbonitrile (XII), 10.7 ml of water, 3.66 g (65.5 mmol) of iron powder and a spoon tip of iron trichloride are charged into a flask. The mixture is heated up to ca. 60°C and 1.5 ml (17.0 mmol) of concentrated hydrochloric acid are added dropwise at this temperature. The mixture is heated up in a bath at the temperature of 90°C for 2.5 hours and is diluted with methanol (10 ml) and chloroform (50 ml). Still being hot, the mixture is filtered over a kieselguhr layer. The organic phase is separated and the aqueous phase is shaken with chloroform (1x 10 ml). The combined organic fractions are then dried with anhydrous sodium sulfate. After evaporation of the solvent the obtained dark oil is purified in a chromatographic column. 1.85 g (5,3 mmol) of the pure product are obtained.'H-NMR (CDC13) δ 1.85-1.96 (2H, m), 2.08 (3H, s), 2.87 (2H, t, J=8.7 Hz), 3.50 (2H, t, J=8.7 Hz), 3.55 (2H, t, J=6.2 Hz), 3.61 (2H, t, J=7.4 Hz), 4.43 (2H, s), 6.83-6.85 (2H, m), 7.18-7.27 (5H, m).
206
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57%
With hydrogenchloride; zinc in 1,4dioxane
4 h; Heating;
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Rx-ID: 3588732
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Kucklaender, Uwe; Bastian, Udo
Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1987 , vol. 42, # 12 p. 1567 - 1577 Title/Abstract Full Text Show Details
207
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Multi-step reaction with 4 steps 1.1: ethanol; sodium tetrahydroborate / tetrahydrofuran / 2 h / 0 - 32 °C / Inert atmosphere 1.2: 1 h / 25 - 32 °C / pH 4.1 2.1: trichlorophosphate / 1 h / 0 - 55 °C / Inert atmosphere 2.2: 17.5 h / 0 - 32 °C 2.3: 1 h / 25 - 32 °C 3.1: hydroxylamine hydrochloride; pyridine / tetrahydrofuran / 1 h / 25 - 60 °C / Inert atmosphere 3.2: 6 h / 50 - 60 °C 4.1: potassium carbonate; N,N-dimethylformamide / 25 - 32 °C / Inert atmosphere 4.2: 4 h / 50 - 60 °C / Inert atmosphere View Scheme
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Rx-ID: 32763302
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RANBAXY LABORATORIES LIMITED; ARYAN, Ram, Chander; SHARMA, Ramnik; NAIDU, Pudi, Giri; MISHRA, Anamika
Patent: WO2012/14186 A1, 2012 ; Title/Abstract Full Text Show Details
208
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Rx-ID: 2241222
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With tri-n-butyl-tin hydride; ozone
1) methylene chloride, 24h, roomtemp., 2) -78 deg C up to room temp.; Multistep reaction;
Palomo, Claudio; Aizpurua, Jesus M.; Cossio, Fernando P.; Garcia, Jesus M.; Lopez, M. Concepcion; Oiarbide, Mikel
Journal of Organic Chemistry, 1990 , vol. 55, # 7 p. 2070 - 2078 Title/Abstract Full Text View citing articles Show Details
A
B
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209
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Rx-ID: 36902514
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Stage #1: β-methyl-β-nitrostyrene With C32H28F6N4O3 in 1,2-dichloroethane; toluene
T=20°C; 0.166667 h; Stage #2: (E)-4-(2-(tosylamino)phenyl)but3-en-2-one in 1,2-dichloro-ethane; toluene T=20°C; 24 h; Overall yield = 90 percent; enantioselective reaction;
Yang, Wen; He, Hai-Xiao; Gao, Yu; Du, Da-Ming
Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3670 - 3678 Title/Abstract Full Text View citing articles Show Details
210
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Stage #1: With acetic acid; zinc in ethanol T=60°C; 1.5 h; Stage #2: With hydrochlorid acid in methanol; ethanol; water
T=60°C; 4 h;
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Rx-ID: 41079013
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Takada, Hisashi; Kumagai, Naoya; Shibasaki, Masakatsu
Organic Letters, 2015 , vol. 17, # 19 p. 4762 - 4765 Title/Abstract Full Text View citing articles Show Details