Sulfuric Acid → Methyl 3-Hydroxy-2-pyridinecarboxylate

HRID 1181328Notes

Reaction equation

HRID 1181328 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.[C:16](=O)([O-])O.[Na+]>CO>[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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 134013-Hydroxypicolinic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Hydroxypicolinic acid (1.0 g) was suspended in methanol (10 ml) and concentrated sulfuric acid (1.0 ml) was added. The mixture was refluxed under heating for 5 hr. The reaction mixture was ice-cooled, neutralized with saturated aqueous sodium hydrogencarbonate, and extracted with chloroform. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (711 mg, yield 64%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 5 hr
  3. temperaturecooled
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf991a5419da4193b2ca1253e1135990
Source dataset
uspto-grants-2007_10
Patent number
US07285551B2

Reaction notes

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