2-Naphthylacetonitrile → 2-(2-Naphthyl)ethyl-amine

Participants

Reaction Conditions

Reaction Steps

Aluminum trichloride (7.6 g, 57 mmole) was added in portions to 30 mL of ether cooled to 0° C. under nitrogen. In a separate flask, lithium aluminum hydride (2.2 g, 57 mmole) was slurried in 30 mL of ether and cooled to -5° C. with an ice/acetone bath. The etherial aluminum trichloride solution was added dropwise to the LiAlH4 slurry at such a rate as to maintain a temperature of 0° C. Fifteen minutes after addition was complete, 2-naphthylacetonitrile (4.0 g, 24 mmole) in 40 mL of ether was added dropwise while maintaining a temperature of 0° C. The reaction mixture was stirred for an additional 15 minutes at 0° C. and then allowed to warm to room temperature for 1 hour. After recooling to 0° C., the reaction was quenched by careful dropwise addition of water. The mixture was diluted with ether, partitioned, and the aqueous phase was basified with 30% NH4OH solution. Extraction of the aqueous phase with ether, combination of the organic phases, drying, and concentration gave a colorless oil (2.7g, 67% yield).

Provenance & Evidence