Triethylamine → 6-Chloro-N-methylnicotinamide

Participants

Reaction Steps

To a stirred solution of 6-chloropyridine-3-carbonyl chloride (1.5 g, 8.52 mmol) in DCM (10 ml) at 0° C. was added methylamine hydrochloride (1.73 g, 25.5 mmol) followed by drop wise additional of triethylamine (3.55 ml, 25.5 mmol) over 10 mins. The reaction mixture was stirred at RT for 2 h then quenched by addition of brine (15 ml) and saturated Na2CO3 (5 ml). The organic layer was collected and the aqueous layer extracted with DCM (2×20 ml). The combined organic phase was washed with brine (10 ml), dried (Na2SO4), filtered and evaporated to dryness. Recrystallisation from hot DCM (˜10 ml) provided the title compound (0.995 g, 5.8 mmol, 68%) as white crystals.

Provenance & Evidence