Dimethylformamide → Methyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 500549Notes

Reaction equation

HRID 500549 reaction equation
O=C1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=CN1.[C:11](=O)([O-])[O-].[K+].[K+].IC.[CH3:19][N:20]([CH:22]=[O:23])[CH3:21]>O>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[CH:19][N:20]([CH3:21])[C:22](=[O:23])[CH:7]=1)=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2807562-Hydroxyisonicotinic Acid

Product 1

HCID 819408Methyl 1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Oxo-1,2-dihydropyridine-4-carboxylic acid (5.0 g, 36 mmol) and potassium carbonate (24.8 g, 179 mmol) were stirred in DMF (75 mL) at room temperature. Iodomethane (6.72 mL, 108 mmol) was added slowly via a syringe and the reaction mixture was stirred for 3 days at room temperature. The reaction mixture was then diluted with water and extracted with dichloromethane until the product was removed from the aqueous phase. The combined organics were dried over magnesium sulfate, filtered and concentrated, then chromatographed in ethyl acetate on silica gel to yield the title compound (4 g, 66%).

Workup

  1. extractionextracted with dichloromethane until the product
  2. customwas removed from the aqueous phase
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed in ethyl acetate on silica gel

Sources & evidence

ORD record
ord-e8fe6ce7396c44cf8e8783283935861b
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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