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Azobisisobutyronitrile → 3-Benzoyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline

HRID 1684574
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HRID 1684574 반응식
[C:1]([C:9]1[C:10]([CH3:33])=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[CH:16][C:15]([O:29][CH3:30])=[C:14]([O:31][CH3:32])[CH:13]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:34]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([C:9]1[C:10]([CH2:33][Br:34])=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[CH:16][C:15]([O:29][CH3:30])=[C:14]([O:31][CH3:32])[CH:13]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19039879HCID 19039879, 화합물

생성물 1

HCID 190399113-Benzoyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline수율 42.1%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 3-benzoyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline (5.5 g), N-bromosuccinimide (2.42 g), 2,2'-azobis(isobutyronitrile)(0.815 g) and carbon tetrachloride (250 ml) was stirred under reflux for 1.5 hours. The reaction mixture was cooled, and then the insoluble material was filtered off. The filtrate was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (10:1, v/v) gave 3-benzoyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (2.73 g, 42%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 182°-183° C.

후처리

  1. temperatureunder reflux for 1.5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe insoluble material was filtered off
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe fractions eluted with chloroform-ethyl acetate (10:1

출처 및 근거

ORD 기록
ord-169bdaf4e5164459a3bc533f19ae0dce
출처 데이터셋
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05641788

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