Methanol → Methyl 6-methylpyridine-2-carboxylate

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Reaction Steps

Concentrated sulfuric acid (5 mL) was added cautiously with stirring to a suspension of 6-methyl-pyridine-2-carboxylic acid (available from Aldrich Chemical Company, Inc., Milwaukee, Wis.; 7.00 g, 51 mmol) in methanol (approximately 250 mL). The mixture was heated at reflux overnight (with a calcium chloride drying tube) and then the solution was concentrated almost to dryness. A little water was added and then aqueous sodium bicarbonate was added to bring the pH to 8. The solution was extracted with ethyl acetate (2×100 mL) and the extracts were washed with brine, then dried (magnesium sulfate), filtered, and evaporated to give 6-methyl-pyridine -2-carboxylic acid methyl ester (3.53 g, 46%) as a pale yellow oil. Mass spectrum m/z 152.

Provenance & Evidence