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

HRID 1385921Notes

Reaction equation

HRID 1385921 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. 1H-NMR (400 MHz, CDCl3) δ value: 3.70(3H,s), 6.75(1H,d), 6.90(2H,m), 7.43(1H,d), 7.58(1H,m)ppm.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing
  3. extractionextracted with ethyl acetate
  4. washAfter washing with 1N hydrochloric acid and water
  5. customthe organic layer was dried over anhydrous
  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-920bf4ea69484435b1d1caa302a438b2
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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