Methanol → HCID 68491536, compound

HRID 658357Notes

Reaction equation

HRID 658357 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:12]([OH:14])=[O:13])[C:3]1=[O:15].[C:16](Cl)(=O)C(Cl)=O.CO.C(N(CC)CC)C>ClCCl.CN(C=O)C>[CH3:16][O:13][C:12]([C:4]1[C:3](=[O:15])[N:2]([CH3:1])[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=1)=[O:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68494030HCID 68494030, compound

Product 1

HCID 68491536HCID 68491536, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1,2-dihydro-1-methyl-2-oxo-6-(trifluoromethyl)pyridine-3-carboxylic acid (114.0 g, 0.52 mol) was dissolved in dichloromethane (500 mL), and oxalyl chloride (99 g, 0.78 mol) was added thereto at room temperature. Thereto, N,N′-dimethylformamide (1 mL) was added, and the mixture was refluxed for 2 hours under heating. The solvent was distilled off, acetonitrile (500 mL) was added, and a mixture of methanol (33 g, 1.03 mol) and triethylamine (104 g, 1.03 mol) was added dropwise under ice cooling. After the 2 hours reaction at room temperature, the solvent was distilled off, an aqueous sodium bicarbonate solution was added, and extraction with chloroform was subjected. The organic layer was washed with an aqueous solution of citric acid and water, dried, and concentrated. Thus obtained oily product was purified by column chromatography (elution solvent: hexane/ethyl acetate=4/1 to 1/1) to obtain 113.5 g of a desired product (yield: 94%).

Workup

  1. customat room temperature
  2. temperaturethe mixture was refluxed for 2 hours
  3. temperatureunder heating
  4. distillationThe solvent was distilled off
  5. additionacetonitrile (500 mL) was added
  6. additionwas added dropwise under ice cooling
  7. customAfter the 2 hours reaction at room temperature
  8. distillationthe solvent was distilled off
  9. additionan aqueous sodium bicarbonate solution was added
  10. extractionextraction with chloroform
  11. washThe organic layer was washed with an aqueous solution of citric acid and water
  12. customdried
  13. concentrationconcentrated
  14. customThus obtained oily product was purified by column chromatography (elution solvent: hexane/ethyl acetate=4/1 to 1/1)

Sources & evidence

ORD record
ord-fdb16fbb5888467eb32c40d709f6d513
Source dataset
uspto-grants-2011_12
Patent number
US08076487B2

Reaction notes

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