反应详情

温度

110 °C

A mixture of methyl 3-chloro-4-nitrophenylacetate (10.9 g, 47.5 mmol), reduced iron powder (8.58 g, 153.6 mmol), AcONa.3H2O (6.05 g, 44.5 mmol) and AcOH (17.6 ml) in MeOH/H2O (100/400 ml) was heated at 110° C. for 1 h. After cooled to room temperature, the reaction mixture was filtered through Celite and the filtered cake was washed with MeOH. The combined filtrate were evaporated and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel [150 g, CHCl3/EtOAc (10/1)] to give methyl 4-amino-3-chlorophenylacetate (4.58 g, 48%) as a red oil. 1H-NMR (CDCl3) δ3.49 (s, 2H), 3.68 (s, 3H), 4.01 (br, 2H), 6.70 (d, J=7.4 Hz, 1H), 6.96 (dd, J=8.1, 2.0 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H).

1. temperatureAfter cooled to room temperature
2. filtrationthe reaction mixture was filtered through Celite
3. washthe filtered cake was washed with MeOH
4. customThe combined filtrate were evaporated
5. extractionextracted with EtOAc
6. washThe combined extracts were washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated in vacuo
9. customThe residue was chromatographed on silica gel [150 g, CHCl3/EtOAc (10/1)]