Ammonia → 3-Amino-2-(p-fluorobenzoyl)crotononitrile

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Reaction Steps

Approximately 50 ml. of liquid ammonia is condensed in a three-neck flask cooled to -78° in a dry ice-acetone bath. To this is added 200 mg. of sodium metal, followed by 100 mg. of ferric chloride hexahydrate. When the blue color had vanished, 6.2 g. of 2-(p-fluorobenzoyl)-3-methoxycrotononitrile is added. After stirring for one hour, the reaction is allowed to warm and the solvent evaporate. The residue is dissolved in hot ethyl acetate and filtered through Celite®. The filtrate is concentrated on the steam bath and diluted with hexane. Upon cooling, the crystalline product precipitates, is filtered and dried.

Provenance & Evidence