Diethyl Carbonate → 2-(4-Chloro-2-pyridinyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-2-methylpyridine (1.28 g) in diethyl ether (15 ml) was treated at −70° C. dropwise with a 2M lithium diisopropylamide heptane/THF solution (6.0 ml) and stirred at −70° C. for 30 minutes. The mixture was treated dropwise also with diethyl carbonate (1.45 ml) at −70° C., and stirred at −70° C. for 1 hour. The reaction mixture was allowed to warm to room temperature, and combined with aqueous sodium bicarbonate and dichloromethane, and the organic phase was isolated, dried and concentrated. A mixture of the resultant residue and a 13% solution of ammonia in methanol (5 ml) was stirred at 75° C. for 7 hours. The reaction mixture was concentrated, and the resultant residue was triturated from diethylether to obtain the title compound (0.47 g) as a tan powder.

Provenance & Evidence