Methanol → Methyl 6-methylpyridine-2-carboxylate

HRID 2112998Notes

Reaction equation

HRID 2112998 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=1.[CH3:16]O>>[CH3:16][O:14][C:13]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:6])[N:12]=1)=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 702826-Methylpyridine-2-carboxylic acid

Product 1

HCID 73022Methyl 6-methylpyridine-2-carboxylateYield 46%

Procedure

Concentrated sulfuric acid (5 mL) was added cautiously with stirring to a suspension of 6-methyl-pyridine-2-carboxylic acid (available from Aldrich Chemical Company, Inc., Milwaukee, Wis.; 7.00 g, 51 mmol) in methanol (approximately 250 mL). The mixture was heated at reflux overnight (with a calcium chloride drying tube) and then the solution was concentrated almost to dryness. A little water was added and then aqueous sodium bicarbonate was added to bring the pH to 8. The solution was extracted with ethyl acetate (2×100 mL) and the extracts were washed with brine, then dried (magnesium sulfate), filtered, and evaporated to give 6-methyl-pyridine -2-carboxylic acid methyl ester (3.53 g, 46%) as a pale yellow oil. Mass spectrum m/z 152.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight (with a calcium chloride drying tube)
  3. concentrationthe solution was concentrated almost to dryness
  4. additionA little water was added
  5. additionaqueous sodium bicarbonate was added
  6. extractionThe solution was extracted with ethyl acetate (2×100 mL)
  7. washthe extracts were washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-390610813a944c9ca4f37125ba6c6444
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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