Hydrochloric Acid → 2-(3-Methoxy-4-nitrophenyl)ethylamine

Participants

Reaction Steps

Under ice cooling, 17.0 g of 2-(3-methoxy-4-nitrophenyl)acetonitrile in 50 ml of tetrahydrofuran is combined with 180 ml of 1-molar borane-tetrahydrofuran complex in tetrahydrofuran, stirred for 16 hours at room temperature, and mixed with water. The mixture is agitated at 0° C. for 0.5 hour, 200 ml of 2N hydrochloric acid is added dropwise, and the mixture is again stirred for 2 hours at 0° C. and for 2 hours at room temperature. A pH of 9.5°-10.5 is set with sodium hydroxide solution, and the mixture is extracted four times with ethyl acetate/butanol 10:1. The product is chromatographed on silica gel with methanol/dichloromethane 1:1, thus obtaining 9.0 g of 2-(3-methoxy-4-nitrophenyl)ethylamine as an oil.

Provenance & Evidence