Sodium Chloride → 1-(2,6-Dimethyl-4-nitrophenyl)-3-methoxypyridin-2(1H)-one

HRID 218505Notes

Reaction equation

HRID 218505 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.[CH3:10][C:11]([CH3:14])([O-])[CH3:12].[K+].F[C:17]1C=C(C)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=1C.[Cl-].[Na+]>CN(C=O)C.O>[CH3:10][C:11]1[CH:14]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=[C:18]([CH3:17])[C:12]=1[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]1=[O:9]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 887313-Methoxy-2-pyridoneHCID 232344381-Fluoro-2,5-dimethyl-4-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 594102131-(2,6-Dimethyl-4-nitrophenyl)-3-methoxypyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

336 mg (2.69 mmol) of 3-methoxypyridinone in 10 ml of DMF are admixed at 0° C. with 452 mg (4.03 mmol) of potassium tert-butoxide, and the mixture is stirred at room temperature for 30 min. 500 mg (2.96 mmol) of 1-fluoro-2,5-dimethyl-4-nitrobenzene are added and the mixture is stirred at 80° C. After 22 h, the mixture is heated to 120° C. and stirred for a further 20 h. Then the mixture is cooled and added to 100 ml of water and 15 ml of saturated aqueous sodium chloride solution. Extraction is effected three times with 300 ml each time of ethyl acetate, and the combined organic phases are dried over sodium sulfate. After filtration, the solvents are removed under reduced pressure and the residue is purified by chromatography on silica gel (1:1 cyclohexane/ethyl acetate). This affords 383 mg (52% of theory) of the desired compound.

Workup

  1. stirringthe mixture is stirred at 80° C
  2. waitAfter 22 h
  3. temperaturethe mixture is heated to 120° C.
  4. stirringstirred for a further 20 h
  5. temperatureThen the mixture is cooled
  6. extractionExtraction
  7. dry with materialthe combined organic phases are dried over sodium sulfate
  8. filtrationAfter filtration
  9. customthe solvents are removed under reduced pressure
  10. customthe residue is purified by chromatography on silica gel (1:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-51f2773f63d7486fa3cf97723f28cb10
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

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