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

HRID 85231

Reaction equation

HRID 85231 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[CH3:7][O:8][C:9]1[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=1.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>[CH3:1][C:2]1[CH:5]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=[C:18]([CH3:17])[C:3]=1[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH3:7])[C:10]1=[O:15]

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

At 0° C., 452 mg (4.03 mmol) of potassium tert-butoxide are added to 336 mg (2.69 mmol) of 3-methoxypyridinone in 10 ml of DMF, 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 at 120° C. and stirred for a further 20 h. The mixture is then cooled and added to 100 ml of water and 15 ml of saturated aqueous sodium chloride solution. The mixture is extracted three times with in each case 300 ml of ethyl acetate, and the combined organic phases are dried over sodium sulphate. After filtration, the solvents are removed under reduced pressure and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1). This gives 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 at 120° C.
  4. stirringstirred for a further 20 h
  5. temperatureThe mixture is then cooled
  6. extractionThe mixture is extracted three times with in each case 300 ml of ethyl acetate
  7. dry with materialthe combined organic phases are dried over sodium sulphate
  8. filtrationAfter filtration
  9. customthe solvents are removed under reduced pressure
  10. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-00c5fd4c2a594e26b59589a8b3dbe3c7
Source dataset
uspto-grants-2014_09
Patent number
US08846934B2

Linked notes

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