反应详情

温度

90 °C

Hydrazine hydrate (7.8 g, 154 mmol) was added to a suspension of 2-{[3-bromo-2-(methyloxy)phenyl]methyl}-1H-isoindole-1,3(2H)-dione (26.7 g, 77.2 mmol) in EtOH (300 mL) and the reaction mixture was heated to 90° C. for 4 h. After cooling to room temperature, the mixture was filtered and the solid was washed with EtOAc (300 mL×2). The filtrate was evaporated to about 50 mL and filtered again. After removing the solvent, the residue was dissolved in 20 mL of MeOH, and then 1N HCl was added to obtain a white solid. Then the white solid was recrystallized from MeOH-Et2O to obtain 9.0 g of the product (yield: 46.3%). 1H NMR (400 MHz, D2O) δ 3.79 (s, 3H), 4.13 (s, 2H), 7.02 (t, J=7.6 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H); 13C NMR (100 MHz, D2O) δ 37.7, 60.2, 115.6, 125.3, 126.6, 128.8, 133.8, 153.7; MS: m/z 254.1 (M+); HPLC: retention time: 7.618 min; purity: 98.8%.

1. temperatureAfter cooling to room temperature
2. filtrationthe mixture was filtered
3. washthe solid was washed with EtOAc (300 mL×2)
4. customThe filtrate was evaporated to about 50 mL
5. filtrationfiltered again
6. customAfter removing the solvent
7. dissolutionthe residue was dissolved in 20 mL of MeOH
8. addition1N HCl was added
9. customto obtain a white solid
10. customThen the white solid was recrystallized from MeOH-Et2O