Triethylamine → N-(2-propynyl)-2-naphthalenecarboxamide

Participants

Reaction Steps

Propargylamine (0.80 mL) and triethylamine (1.67 mL) were added simultaneously to a solution of 2-naphthoyl chloride (2.22 g) in dichloromethane (25 mL) cooled in an ice bath. The mixture was held at 0° C. for 1 hour and allowed to warm to room temperature over 3 hours. The solution was diluted with ethyl acetate, washed in turn with water, 1N hydrochloric acid, 1N sodium hydroxide, and saturated brine. Evaporation of the dried (K2CO3) organic layer gave a residue which was crystallized from dichloromethanehexane to give 2.06 g of N-(2-propynyl)-2-naphthalenecarboxamide, mp 163°-165° C.

Provenance & Evidence