Methanol → Methyl 6-methylpyridine-2-carboxylate

HRID 1176756Notes

Reaction equation

HRID 1176756 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[CH3:16][O:9][C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:10]

Participants

4

Reactant 3

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

Product 1

HCID 73022Methyl 6-methylpyridine-2-carboxylateYield 59%

Procedure

A mixture of 6-methyl-pyridine-2-carboxylic acid (10 g, 72.9 mmol) and concentrated sulfuric acid (3.5 mL) in methanol (300 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was poured into saturated aqueous sodium hydrogen carbonate (250 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried (magnesium sulfate), filtered, and evaporated to give 6-methyl-pyridine-2-carboxylic acid methyl ester (6.5 g, 59%) as a colorless oil. 1HNMR (CDCl3): δ 7.97 (d, J=7.6 Hz, 1H), 7.73 (dd, J=7.6 Hz, 1H), 7.36 (d, J=7.6 Hz, 1H), 4.01 (s, 3H), 2.67 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was poured into saturated aqueous sodium hydrogen carbonate (250 mL)
  5. extractionextracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic layers were dried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3c10839e221a460d846381908bae0d32
Source dataset
uspto-grants-2010_11
Patent number
US07842825B2

Reaction notes

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