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

HRID 218511

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HRID 218511 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa728b67579c4200925a08884f0fba41
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198267B2

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