Hydrazine hydrate (1:1) → 3-Chloroisoquinoline

Participants

Reaction Steps

A mixture of 1,3-dichloroisoquinoline (9.94 g, 50.2 mmol) and hydrazine hydrate (12.2 ml, 251 mmol) in ethanol (150 ml) was heated at reflux for 1.5 hours. The reaction was then cooled to room temperature and the ethanol evaporated. The residue was suspended in chloroform and manganese dioxide (20 g) was added in portions over 30 minutes. Gas evolution was observed. After this had subsided, the mixture was heated to reflux for 2 hours, then filtered and evaporated. Purification of the residue by flash column chromatography using dichloromethane as eluant gave the title compound (3.5 g).

Provenance & Evidence