In a three-necked flask, 3-methoxy-5-nitrobenzonitrile (8.0 g, 0.045 mol) was dissolved in methanol (80 mL), 10% palladium-carbon catalyst (1.4 g) and ammonium acetate (6.9 g, 0.090 mol) were added. Hydrogen was introduced and the reaction was stirred at 40 °C for 8 hours. After completion of the reaction, filtration was carried out and the filter cake was washed with methanol (15 mL x 3). The filtrates were combined and concentrated under reduced pressure. The concentrate was poured into 50 mL of water and extracted with ethyl acetate (40 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure to give 3-amino-5-methoxybenzonitrile as a solid 6.5 g in 98.2% yield.
