3-Bromophenylhydrazine hydrochloride → 1-(3-Bromophenyl)-3-(tert-butyl)-1H-pyrazol-5-amine

Participants

Reaction Steps

A mixture of (3-bromophenyl)hydrazine hydrochloride (22.2 g, 0.1 mol) and 4,4-dimethyl-3-oxo-pentanenitrile (18.7 g, 0.15 mol) in EtOH (250 mL) was heated at reflux overnight. The reaction was concentrated and the residue purified via column chromatography to yield 2-(3-bromophenyl)-5-t-butyl-2H-pyrazol-3-ylamine as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.85 (s, 1H), 7.68 (d, J=7.6 Hz, 1H), 7.62 (d, J=7.2 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 5.62 (s, 1H), 1.27 (s, 9H).

Provenance & Evidence