Pyridine → HCID 10938596, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of dibenzyloxyacetic acid (4.0 g, prepared as described in Step 2) in dichloromethane (40 ml) was cooled to 0° C. and treated dropwise with, successively, 4-N,N-dimethylformamide (100 mg) and oxalyl chloride (2.0 g). After thirty minutes, pyridine (3.52 g), 3-trifluoromethyl aniline (2.64 g) and 4-dimethylaminopyridine (100 mg) were added. The mixture was stirred at 0° C. for a further thirty minutes then allowed to warm to room temperature. After three hours, it was poured into water, extracted with ethyl acetate and the extracts washed successively with dilute hydrochloric acid, water, aqueous sodium bicarbonate solution, and brine. After drying over magnesium sulphate, the extracts were evaporated under reduced pressure to give the title compound (5.62 g) as an orange gum, sufficiently pure to be used in Step 4.

Provenance & Evidence