16554-47-5

158461-29-1

16554-47-5

General procedure for the synthesis of 2-nitro-3-methoxyaniline from tert-butyl (3-methoxy-2-nitrophenyl)carbamate: to a stirred solution of tert-butyl (3-methoxy-2-nitrophenyl)carbamate (13.3 g, 49.6 mmol) in dichloromethane (100 mL) was added trifluoroacetic acid (20 mL) and the reaction mixture was stirred for 4 hours at room temperature . Subsequently, the mixture was concentrated under vacuum to give a residue which was dissolved in ethyl acetate. The resulting solution was poured into saturated aqueous sodium bicarbonate solution, the organic layer was separated, washed with brine, dried with anhydrous sodium sulfate and concentrated under vacuum. The resulting precipitate was ground with hexane and filtered to afford 2-nitro-3-methoxyaniline (7.55 g, 44.9 mmol, 91% yield) as a yellow solid.1H NMR (CDCl3, 400 MHz): δ 3.88 (3H, s), 6.31 (1H, dd, J = 8.6,1.2 Hz), 7.36 (1H, dd, J = 8.6,1.2Hz), 7.16 (1H, t, J = 8.6Hz).