Hydrochloric Acid → 1-(2-Chloro-4-nitrophenyl)-3-methoxypyridin-2(1H)-one

HRID 218503

반응식

HRID 218503 반응식
[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[Cl:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F.Cl>CS(C)=O>[Cl:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]1=[O:9]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 887313-Methoxy-2-pyridoneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 595867481-(2-Chloro-4-nitrophenyl)-3-methoxypyridin-2(1H)-one

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

15 g (120 mmol) of 3-methoxypyridone are dissolved in 120 ml of anhydrous dimethyl sulfoxide and admixed with 16.1 g (144 mmol) of potassium tert-butoxide with stirring. After 30 min, 21.0 g (120 mmol) of 3-chloro-4-fluoronitrobenzene are added and the mixture is heated to 80° C. After 16 h, the mixture is allowed to cool, admixed with 1N hydrochloric acid and extracted repeatedly with dichloromethane. The combined dichloromethane phases are washed with water and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. The resulting residue is stirred with tert-butyl methyl ether and filtered. The solid is dried under reduced pressure. 22.8 g (60% of theory) of the desired compound are obtained.

후처리

  1. waitAfter 16 h
  2. temperatureto cool
  3. extractionextracted repeatedly with dichloromethane
  4. washThe combined dichloromethane phases are washed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. stirringThe resulting residue is stirred with tert-butyl methyl ether
  9. filtrationfiltered
  10. customThe solid is dried under reduced pressure

출처 및 근거

ORD 기록
ord-968b7a033bb046329421c1ce765e1eb2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198267B2

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