Sodium Hydroxide → Hydrazine, [4-bromo-2-(phenylmethoxy)phenyl]-, hydrochloride (1:1)

Participants

Reaction Conditions

Reaction Steps

To a stirred slurry of 2-(benzyloxy)-4-bromoaniline (12.60 g, 45.3 mmol) in concentrated HCl (150 mL) was added a solution of sodium nitrite (3.44 g, 49.9 mmol) in water (20 mL). The reaction mixture was stirred at 0° C. for 30 min before adding a slurry of tin dichloride (25.8 g, 136.0 mmol) in concentrated HCl (35 mL). The reaction mixture was stirred at 0° C. overnight, warmed to ambient temperature, made basic to pH 10 by addition of sodium hydroxide and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate and treated with 1.25M HCl in methanol (10 mL). The solution was concentrated in vacuo to give (2-(benzyloxy)-4-bromophenyl)hydrazine hydrochloride (5.64 g, 38%) as a brown solid: 1H NMR (CD3OD, 300 MHz) δ 7.31-7.47 (m, 5H), 7.06 (dd, J=8.4, 2.1 Hz, 1H), 6.96 (d, J=2.1 Hz, 1H), 6.86 (d, J=8.4 Hz, 1H), 5.01 (s, 2H).

Provenance & Evidence