Isoamyl Nitrite → N-Hydroxybenzimidoyl cyanide

Participants

Reaction Steps

A solution of isopentyl nitrite (16.00 g, 137 mmol) in EtOH (30 mL) was added dropwise to a solution of 2-phenylacetonitrile (16 g, 137 mmol) and sodium hydroxide (5.46 g, 137 mmol) while cooling in an ice bath. Once the addition was complete, the mixture was allowed to warm to room temperature. After stirring at room temperature for 2 h, the reaction was diluted with diethyl ether. The resultant precipitate was filtered and washed with diethyl ether. The solid was air dried and then vacuum dried to yield the titled compound (10 g, 68.9 mmol, 50.4% yield) as a light yellow solid.

Provenance & Evidence