Sodium Hydroxide → 3-(2-aminophenyl)propan-1-ol

Participants

Reaction Steps

To a solution of ethyl 3-(2-nitrophenyl)acrylate (1.11 g) in diethyl ether (30 mL) was added a 1M diisobutylaluminum hydride solution in hexane (15.0 mL) under ice cooling. After stirring the solution under ice cooling for 1 hour, diethyl ether, water (0.6 mL) and a 15% aqueous sodium hydroxide solution (0.6 mL) were added thereto. The solution was stirred at room temperature for 15 minutes. Water (1.8 mL) was then added and the solution was stirred at room temperature for 15 minutes. Anhydrous magnesium sulfate was added to the solution and filtered. The filtrate was concentrated under reduced pressure. To a solution of the resulting residue in ethanol (50 mL) was added 10% palladium-carbon (200 mg). The mixture was stirred at room temperature under hydrogen atmosphere for 89 hours. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=1:2) to give the title compound (660 mg).

Provenance & Evidence