Carbon Tetrachloride → Methyl 2-methoxypyridine-3-carboxylate

Participants

Reaction Steps

A mixture of 2-methoxy-nicotinic acid (5.00 g, 32.6 mmol), thionyl chloride (50 mL) and carbon tetrachloride (50 mL) was head at reflux for 2 h. The reaction mixture was allowed to cool and volatiles were removed on a rotary evaporator. The residue was co-evaporated three times with carbon tetrachloride to remove residual oxalyl chloride. Methanol (50 mL) was added and the mixture was stirred at room temperature overnight. The solvent was evaporated and chloroform (150 mL) was added. The solution was washed with saturated aqueous sodium hydrogen carbonate (2×150 mL) and brine (150 mL), dried (magnesium sulfate), filtered, and evaporated to give 2-methoxy-nicotinic acid methyl ester (4.42 g, 81%) as a clear yellow oil.

Provenance & Evidence