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

HRID 218504

반응식

HRID 218504 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+].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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

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 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

출처 및 근거

ORD 기록
ord-ff66636a79984f4390ae566357b10ac0
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198267B2

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