Hydrochloric Acid → 3-Methoxy-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

HRID 85220

反応式

HRID 85220 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+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[CH3:26].Cl>CS(C)=O.O>[CH3:1][O:2][C:3]1[C:4](=[O:9])[N:5]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[CH3:26])[CH:6]=[CH:7][CH:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 887313-Methoxy-2-pyridoneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 594101653-Methoxy-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

28.5 g (228 mol) of 3-methoxypyridin-2(1H)-one are dissolved in 850 ml of dimethyl sulphoxide, and 31 g (273 mmol) of potassium tert-butoxide are added at RT. The suspension is stirred at RT for 30 min, and 35 g (228 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are then added, and the reaction solution is heated at 80° C. for 20 h. The solution is then carefully diluted with 1 l of water and adjusted to pH 1-2 using 1N hydrochloric acid. The solution is extracted repeatedly with dichloromethane. The combined organic extracts are washed with water and saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated under reduced pressure. The solid obtained is washed with a little tert-butyl methyl ether, filtered off and dried under reduced pressure. This gives 42.8 g (72% of theory) of the desired compound.

後処理

  1. temperaturethe reaction solution is heated at 80° C. for 20 h
  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 sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe solid obtained
  8. washis washed with a little tert-butyl methyl ether
  9. filtrationfiltered off
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-48a81b494967407ca32565a61606b854
出典データセット
uspto-grants-2014_09
特許番号
US08846934B2

関連ノート

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