Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate

HRID 2178242Notes

Reaction equation

HRID 2178242 reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[C:8]([C:13]([OH:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:16]O>>[OH:6][C:7]1[C:8]([C:13]([O:15][CH3:16])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylateYield 85%

Procedure

Concentrated sulphuric acid (19 mL) was added dropwise to a mixture of 3-hydroxy picolinic acid (23.0 g, 165 mmol) in methanol (700 mL) at rt. The mixture was heated to reflux for 72 hours, cooled and concentrated. The mixture was neutralized with bicarbonate and extracted with EtOAc. The organic phases were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to provide 21.7 g (85%) of the desired product methyl 3-hydroxypicolinate (26A): 1H NMR (300 MHz, CDCl3) δ 10.63 (1H, s), 8.28 (1H, dd), 7.39 (2H, m), 4.06 (3H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 72 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. extractionextracted with EtOAc
  6. washThe organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0aebe35511f341c2bf5ad91d77e40bc2
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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