Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate

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).

1. temperaturewas refluxed for 18 h
2. concentrationThe mixture was concentrated to about 40 mL
3. additiondiluted with water (150 mL)
4. extractionextracted with CHCl3 (100 mL×3)
5. washThe combined organic extracts were washed with water, brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationthe filtrate was concentrated

ORD record

ord-0904c97bea024de28dbb95b17ee01161

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101634B2