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

HRID 657338Notes

Reaction equation

O.NN.[Br:4][C:5]1[C:6]([O:23][CH3:24])=[C:7]([CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)[CH:8]=[CH:9][CH:10]=1>CCO>[Br:4][C:5]1[C:6]([O:23][CH3:24])=[C:7]([CH2:11][NH2:12])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

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%.

Workup

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

Sources & evidence

ORD record: ord-c07b34f963224b368c8b430e7084e1bf
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071588B2

Reaction notes

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