Hydrazine hydrate (1:1) → 2-(cyclohexylmethyl)-1H-pyrrole

Participants

Reaction Steps

A mixture of cyclohexyl pyrrol-2-yl ketone (17.7 g.) and 99% hydrazine hydrate (6.0 ml.) was heated under reflux in diethylene glycol (70 ml.) for 1.5 hours. The excess hydrazine hydrate and water were distilled off and the mixture was cooled. Potassium hydroxide (12.0 g.) was added portionwise and the mixture was then heated under reflux for 4 hours, cooled and poured into water (500 ml.). The mixture was extracted with ether (3×100 ml.) and the combined etheral extracts were washed with water (3×100 ml.) and dried over sodium sulphate. Evaporation of the ether gave an oil which was distilled to give 2-cyclohexylmethylpyrrole (11.3 g.), B.P. 137°-140° at 15 mm.

Provenance & Evidence