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

HRID 218503

反応式

HRID 218503 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-968b7a033bb046329421c1ce765e1eb2
出典データセット
uspto-grants-2012_06
特許番号
US08198267B2

関連ノート

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