4-Methylphenylhydrazine monohydrochloride → 5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine

Participants

Reaction Steps

Heat to reflux a solution of 3-(1-methyl-cyclopropyl)-3-oxo-propionitrile (60 g, 487.2 mmol) and p-tolyl-hydrazine hydrochloride (78 g, 478.2 mmol) in ethanol (975 mL) for 4 hours. Evaporate the solvent and dissolve the remaining solid in water. Increase pH of the solution to pH 8 using a 1.0 N solution of sodium hydroxide. Filter the precipitate to obtain 5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine as a white solid. 1H NMR (DMSO): 7.39 (d, J=8 Hz, 2H), 7.22 (d, J=8 Hz, 2H), 5.12 (s, 2H), 2.31 (s, 3H), 1.30 (s, 3H), 0.80 (q, J=4 Hz, 2H), 0.61 (q, J=4 Hz, 2H).

Provenance & Evidence