Methyl 5-methyl-2-nitrobenzoate (8 g, 41.025 mmol) was used as a raw material in a solvent mixture of methanol (80 mL) and water (10 mL), and cooled to 0 °C. Subsequently, zinc powder (13.33 g, 205.128 mmol) and NH4Cl (17.6 g, 328.2 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 12 h. The reaction progress was monitored by TLC (unfolding agent: 20% ethyl acetate/hexane). After completion of the reaction, the mixture was filtered and the filtrate was evaporated to give the crude product. The crude product was alkalized with saturated NaHCO3 solution and extracted with dichloromethane (2 x 20 mL). The organic layers were combined, dried with Na2SO4, filtered and the solvent was evaporated to give the target compound methyl 2-amino-5-methylbenzoate (yield: 4 g, 60%).1H NMR (400 MHz, CDCl3) data were as follows: δ 7.65 (s, 1H), 7.25 (s, 1H), 7.10-7.07 (q, 1H, J=8Hz), 6.58 (d, 1H), 3.86 (s, 3H), 2.22 (s, 3H).
