Isoamyl Nitrite → N-Hydroxybenzimidoyl cyanide

Participants

Reaction Steps

A solution of isopentyl nitrite (16.00 g, 137 mmol) in ethyl alcohol (30 mL) was added dropwise to a solution of 2-phenylacetonitrile (16 g, 137 mmol) and sodium hydroxide (5.46 g, 137 mmol) in ethyl alcohol (30 mL) at 0° C. Once the addition was complete, the mixture was allowed to warm to room temperature. After stirring for 2h, the reaction mixture was diluted with diethyl ether and the resultant solid was collected by filtration and washed with diethyl ether. The solid was vacuum dried to yield (Z)—N-hydroxybenzimidoyl cyanide (10 g, 68.9 mmol, 50.4% yield) as a light yellow solid.

Provenance & Evidence