Hydrazine hydrate (1:1) → (3-Bromo-2-methoxyphenyl)methanamine

Temperature

90 °C

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), hydrazine hydrate (7.8 g, 154 mmol) was added, and the reaction mixture was heated to 90° C. for 4 h. After cooled to room temperature, the mixture was filtered and the solid was washed with EtOAc (300 mL×2). The filtrate was concentrated 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 with 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, 1 H), 7.27 (d, J=8.0 Hz, 1 H), 7.57 (d, J=8.0 Hz, 1 H); 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. additionwas added
2. temperatureAfter cooled to room temperature
3. filtrationthe mixture was filtered
4. washthe solid was washed with EtOAc (300 mL×2)
5. concentrationThe filtrate was concentrated to about 50 mL
6. filtrationfiltered again
7. customAfter removing the solvent
8. dissolutionthe residue was dissolved in 20 mL of MeOH
9. addition1N HCl was added
10. customto obtain a white solid
11. customThen the white solid was recrystallized with MeOH-Et2O

ORD record

ord-2b367488b46b470996c690b7d3943541

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067408B2