Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate

Participants

Reaction Steps

A mixture of 3-hydroxypicolinic acid (2 g, 14.1 mmol) in MeOH (100 mL) containing concentrated H2SO4 (4 mL) was refluxed for 18 h. The mixture was concentrated to about 40 mL, diluted with water (150 mL), adjusted to pH around 6 with Na2CO3, and then extracted with CHCl3 (100 mL×3). The combined organic extracts were washed with water, brine and dried over Na2SO4, filtered, and the filtrate was concentrated to give 1.71 g (79%) of methyl 3-hydroxy-2-pyridinecarboxylate as off-white crystals. 1H NMR (400 MHz, CDCl3): δ 10.63 (s, 1H), 8.30-8.25 (m, 1H), 7.50-7.35 (m, 2H), 4.06 (s, 3H); LRMS (ESI), m/z 154 (M+H).

Provenance & Evidence