3-(2,4-difluorophenyl)-6-trifluoromethyl-2H-pyran-2-one → 3-(2,4-difluorophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone

HRID 992859Notes

Reaction equation

HRID 992859 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=O)[O:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1.CO.[CH3:22][NH2:23]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](=[O:11])[N:23]([CH3:22])[C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 154571853-(2,4-difluorophenyl)-6-trifluoromethyl-2H-pyran-2-oneHCID 57454252Monomethylamine methanol

Product 1

HCID 154570473-(2,4-difluorophenyl)-1-methyl-6-trifluoromethyl-2(1H)-pyridoneYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13.8 g (50 mmol) of 3-(2,4-difluorophenyl)-6-trifluoromethyl-2H-pyran-2-one was dissolved in 150 ml of ethanol, and 5.5 g (70 mmol) of a 40% methylamine methanol solution was added, followed by stirring for 6 hours under heating and refluxing. The reaction solution was poured into ice water and extracted with ethyl acetate. After washing with 1N hydrochloric acid and water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and then, the obtained residue was purified by silica gel column chromatography to obtain 3.8 g (yield: 26%) of the desired product. Melting point: 123-124° C.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. extractionextracted with ethyl acetate
  4. washAfter washing with 1N hydrochloric acid and water
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. distillationEthyl acetate was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1e827e091ebd45c0bd16f0d1c12aa4e9
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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