Methanol → Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate

HRID 594302Notes

Reaction equation

HRID 594302 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=[CH:3]1.OS(O)(=O)=O.[CH3:16]O>>[O:1]=[C:2]1[NH:7][C:6]([C:8]([O:10][CH3:16])=[O:9])=[CH:5][CH:4]=[CH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2427216-Hydroxypicolinic acid

Product 1

HCID 12342664Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate

Procedure

A mixture of commercially available 6-oxo-1,6-dihydropyridine-2-carboxylic acid (4.000 g; 28.75 mmol) and concentrated H2SO4 (3.5 ml) in anh. MeOH (65 ml) was refluxed, under nitrogen, for 22 h. MeOH was removed under reduced pressure, and the residue was basified by addition of a solution of 10% aq. NaHCO3. The mixture was then extracted with DCM (3×), and the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording methyl 6-oxo-1,6-dihydropyridine-2-carboxylate as a beige solid. LC-MS (conditions D): tR=0.54 min.; no ionisation.

Workup

  1. temperaturewas refluxed, under nitrogen, for 22 h
  2. customMeOH was removed under reduced pressure
  3. additionthe residue was basified by addition of a solution of 10% aq. NaHCO3
  4. extractionThe mixture was then extracted with DCM (3×)
  5. dry with materialthe mixed organic layers were dried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-74ac2210d9c842f5b2ff7b4c6e0a91f4
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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