2-(Ethoxymethylene)propanedinitrile → 5-Amino-4-cyano-1-(2,2-diethoxyethyl)pyrazole

Participants

Reaction Steps

To a solution of hydrazinoacetaldehyde diethyl acetal (52.6 g) in ethanol (110 ml) was added dropwise a solution of ethoxymethylenemalononitrile (41.5 g) in ethanol (420 ml) at room temperature. The mixture was stirred at ambient temperature for 24 hours. The reaction mixture was evaporated in vacuo. To the residue was added diethyl ether (400 ml) and the resultant precipitate was filtered off. The filtrate was subjected to column chromatography on silica gel using a mixture of ethyl acetate and hexane (2:3) as an eluent. Fractions containing the object compound were combined and evaporated to give 5-amino-4-cyano-1-(2,2-diethoxyethyl)pyrazole (23.0 g).

Provenance & Evidence