Triethylamine → 6-Chloro-N-methoxy-N-methylnicotinamide

Participants

Reaction Steps

A suspension of 6-chloronicotinic acid (80 g, 0.5 mol) in thionyl chloride (400 ml) was heated under reflux for 3 hours to give a yellow solution. The mixture was concentrated under reduced pressure, the residue was dissolved in dichloromethane (600 ml) and treated with N,O-dimethylhydroxylamine hydrochloride (56.5 g, 0.58 mol). The suspension was cooled in ice then treated dropwise with triethylamine (220ml, 1.5 mol) and stirred for 1 hour at room temperature. The mixture was filtered, the filtrate was washed with aqueous sodium hydroxide (2N, 200 ml), dried over magnesium sulphate then concentrated under reduced pressure. The resulting liquid was distilled under reduced pressure to yield the title compound (90 g), b.p. 106-110° C. (0.5 mm Hg), which was characterised by 1H-N.M.R. spectroscopy.

Provenance & Evidence