3-Cyano-4-isobutoxyaniline hydrochloride → 3-Cyano-4-isobutoxy-phenylhydrazine

Participants

Reaction Steps

To an aqueous solution (34 ml) of 3-cyano-4-isobutoxyaniline hydrochloride (20 g) were added sodium nitrite (6.8 g), stannous chloride dihydrate (61 g) and con. hydrochloric add (100 ml) with stirring under ice-cooling. After the completion of the reaction, precipitated crystals were collected by filtration. The crystals were added to water, and the mixture was neutralized with aqueous sodium hydroxide solution, extracted with a mixed solvent of toluene and tert-butanol, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 15 g of 3-cyano-4-isobutoxy-phenylhydrazine.

Provenance & Evidence