Benzene, 1-fluoro-2-methyl-4-nitro- → 1-(2-Methyl-4-nitrophenyl)-3-(trifluoromethyl)pyridin-2(1H)-one

HRID 218511

Reaction equation

HRID 218511 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[CH3:28]>CS(C)=O.O>[CH3:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[C:4]1=[O:9]

Participants

6

Reactant 3

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 36784112(1H)-Pyridinone, 3-(trifluoromethyl)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 595867011-(2-Methyl-4-nitrophenyl)-3-(trifluoromethyl)pyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2.5 g (15.3 mmol) of 3-(trifluoromethyl)pyridin-2(1H)-one are dissolved in 40 ml of dimethyl sulfoxide and admixed at room temperature with 2.58 g (22.9 mmol) of potassium tert-butoxide. The suspension is stirred at room temperature for 30 min, before 2.6 g (16.9 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are added and the reaction solution is heated to 80° C. for 20 h. It is diluted cautiously with water. The solution is extracted repeatedly with dichloromethane. The combined organic extracts are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is dissolved in acetonitrile and purified by preparative HPLC with a gradient of water and acetonitrile. The product fractions are combined and concentrated to dryness under reduced pressure. This affords 1.87 g (41% of theory) of the desired product.

Workup

  1. additionare added
  2. extractionThe solution is extracted repeatedly with dichloromethane
  3. washThe combined organic extracts are washed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue is dissolved in acetonitrile
  8. custompurified by preparative HPLC with a gradient of water and acetonitrile
  9. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-aa728b67579c4200925a08884f0fba41
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Linked notes

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