89521-55-1

89521-54-0

89521-55-1

Under nitrogen protection, 2-(benzyloxy)-6-nitroaniline (5 g, 0.02 mol) was dissolved in a mixed solution of acetic acid (50 mL) and ethanol (50 mL) and stirred at 15 °C. To this solution was added iron powder (4.6 g, 0.08 mol). The reaction mixture was heated to 75°C and stirred continuously for 30 minutes. After completion of the reaction, the mixture was concentrated under vacuum. The concentrated residue was dissolved in water (50 mL) and the pH was adjusted with saturated sodium bicarbonate solution to 9. Subsequently, the aqueous phase was extracted with ethyl acetate (50 mL x 3). The organic phases were combined, washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to give 3-(benzyloxy)benzene-1,2-diamine (2.2 g, 77.7% yield) as a yellow oil.LCMS (M+H+) m/z: calculated value 215.12; measured value 215.1.