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

HRID 218504

反応式

HRID 218504 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

反応条件

温度
80 °C

実験手順

28.5 g (228 mol) of 3-methoxypyridin-2(1H)-one are dissolved in 850 ml of dimethyl sulfoxide and admixed at RT with 31 g (273 mmol) of potassium tert-butoxide. The suspension is stirred at RT for 30 min, before 35 g (228 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are added, and the reaction solution is heated to 80° C. for 20 h. The mixture is then cautiously diluted with 1 l of water and brought to pH 1-2 with 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 sulfate, filtered and concentrated under reduced pressure. The resulting solid is washed with a little tert-butyl methyl ether, filtered off and dried under reduced pressure. This affords 42.8 g (72% of theory) of the desired compound.

後処理

  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 sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting solid is washed with a little tert-butyl methyl ether
  8. filtrationfiltered off
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-ff66636a79984f4390ae566357b10ac0
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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