Hydrochloric Acid → (4-Bromo-3-methylphenyl)hydrazine hydrochloride

Participants

Reaction Conditions

Reaction Steps

4-Bromo-3-methylaniline (10.2 g) was suspended in 6N HCl (85 mL) and cooled to 0° C. A solution of sodium nitrite (4 g in 40 mL H2O) was added over 10 min. The reaction was stirred for 15 min at 0° C. followed by the addition of stannous chloride dihydrate (36 g in 25 mL 12N HCl.) The reaction was stirred for 2 hr at 0° C. The reaction was filtered and the filter cake washed with cold H2O to afford 4-bromo-3-methylphenylhydrazine hydrochloride (Cmpd 9a, 20 g) as a tan solid.

Provenance & Evidence