Hydrochloric Acid → Methyl 3-Hydroxy-2-pyridinecarboxylate

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Reaction Steps

To a solution of 3-hydroxypyridine-2-carboxylic acid (100 g, 719 mmol) in anhydrous methanol (300 ml) was added dry HCl gas until the saturation point of the solution was achieved. The reaction was heated to reflux for 15 h and then cooled and degassed with argon. The solution was concentrated in vacuo to give a white solid which was dissolved in water (250 ml). The pH of the solution was adjusted to ˜7.5 with the slow addition of solid sodium bicarbonate. The resulting suspension was extracted with EtOAc (2×300 ml), and the organic portion was dried over magnesium sulfate, filtered, and concentrated in vacuo to yield methyl 3-hydroxypyridine-2-carboxylate as an oily residue which crystallized on standing (99.2 g).

Provenance & Evidence