Methanol → Methyl 2-chloronicotinate

Participants

Reaction Steps

Oxalyl chloride (13.28 ml, 0.15 mmol) was added dropwise to a solution of 2-chloronicotinic acid (24 g, 0.153 mmol) in dichloromethane (250 ml) containing dimethylformamide (10 drops) under nitrogen at room temperature. The reaction was stirred at room temperature for 1.5 h and was then cooled to 0° C. Triethylamine (63.7 ml, 0.457 mmol) was added slowly followed by methanol (60 ml). After stirring at 0° C. for 30 min, the solvent was removed under reduced pressure and the residue was dissolved in sat. sodium bicarbonate solution (200 ml). This was extracted with diethylether (5×100 ml) and the combined organic extracts were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with diethylether to give 2-chloronicotinic acid methyl ester (20.7 g) as a pale yellow oil.

Provenance & Evidence