Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate

HRID 341485Notes

Reaction equation

HRID 341485 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:16]O>>[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:16])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylateYield 55%

Procedure

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%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. stirringstirred for 60 hours
  4. concentrationthen concentrated under vacuum
  5. dissolutionThe residue was dissolved in water (20 ml)
  6. extractionextracted with ethyl acetate (3×20 ml)
  7. washThe combined organic extracts were washed with water
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6c459763b01846ef805559dac8b1409d
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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