Methyl (E)-3-(2-nitrophenyl)acrylate (11.03 g, 53.24 mmol) was dissolved in ethyl acetate (200 mL) at room temperature, followed by the addition of SnCl2-H2O (60.06 g, 266.19 mmol). The reaction mixture was stirred at 70 °C for 60 min. Upon completion of the reaction, the mixture was cooled to room temperature, the pH was adjusted to a weak base with saturated aqueous sodium bicarbonate solution and filtered through diatomaceous earth. The aqueous phase was extracted three times with ethyl acetate, the organic phases were combined and dried with anhydrous magnesium sulfate. After the solvent was removed by distillation under reduced pressure, the residue was purified by silica gel column chromatography (eluent ratio: ethyl acetate:hexane=1:5) to afford methyl (E)-3-(2-aminophenyl)acrylate (8.50 g, 90% yield).1H-NMR (400 MHz, CDCl3) δ 7.92-7.86 (d, 1H, -C-CH=CH-), 7.44- 6.76 (m, 4H, aromatic H), 6.42-6.36 (d, 1H, -C-CH=CH-), 3.83 (s, 3H, -OCH3).
