Triethylamine → N-methoxy-N,5-dimethylnicotinamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-methyl-nicotinic acid (1.8 g, 13.1 mmole) and SOCl2 (10 mL) was heated to 75° C. for three hours. The remaining SOCl2 was removed by vacuum distillation and the oily residue carefully redissolved in dichloromethane (16 mL). Then N,O-dimethylhydroxyl amine hydrochloride (1.4 g, 14.4 mmol) was added. The reaction mixture was purged with argon and triethylamine (5.11 mL, 36.7 mmol) was dropwise added at 0° C. It was stirred for 24 hours at room temperature. The mixture was diluted with dichloromethane, washed with NaOH 2N, brine, dried and concentrated to yield a brown oil which was purified by column chromatography (SiO2, n-Hex/EtOAc 1:1 to EtOAc) to afford the title compound (1.7 g, 71% yield) as a brownish oil.

Provenance & Evidence