The general procedure for the synthesis of methyl 2-amino-5-methoxybenzoate from methyl 5-methoxy-2-nitrobenzoate was as follows: methyl 5-methoxy-2-nitrobenzoate (1.60 g, 7.58 mmol) was dissolved in ethyl acetate (14 mL), and 10% palladium-carbon catalyst (containing 50% water, 320 mg) was added. The reaction was stirred at 20-25°C for 3 hours under hydrogen atmosphere (0.25 MPa). Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration and the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography with hexane/ethyl acetate (10:1 to 5:1) as eluent to afford methyl 2-amino-5-methoxybenzoate (1.29 g, 94% yield). The product was characterized by 1H-NMR (CDCl3), δ: 3.76 (3H, s), 3.88 (3H, s), 5.37 (2H, br), 6.63 (1H, d, J = 8.8 Hz), 6.95 (1H, dd, J = 8.8, 3.1 Hz), 7.35 (1H, d, J = 3.1 Hz).
