Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate

Participants

Reaction Steps

A mixture of 3-hydroxypyridine-2-carboxylic acid (2.0 g, 14.4 mmol), conc sulfuric acid (0.5 ml) and methanol (100 ml) was heated to reflux and stirred for 48 hours. The mixture was cooled to room temperature and stirred for 60 hours then concentrated under vacuum. The residue was dissolved in water (20 ml), basified to pH 8 using solid sodium carbonate (care: gas evolution!) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with water and concentrated under vacuum to give the title compound as a white solid (1.22 g, 55%). Method C HPLC-MS: MH+ requires m/z=154. Found: m/z=154, Rt=0.78 min (100%).

Provenance & Evidence