Nitrobenzene → 8-Methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61691노트

반응식

HRID 61691 반응식
[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.O[C:26]([C:29]1[NH:30][C:31]2[C:36]([CH:37]=1)=[CH:35][CH:34]=[C:33]([C:38]#[N:39])[CH:32]=2)([CH3:28])[CH3:27]>O>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]2[C:20](=[O:21])[C:37]3[C:36]4[C:31](=[CH:32][C:33]([C:38]#[N:39])=[CH:34][CH:35]=4)[NH:30][C:29]=3[C:26]([CH3:28])([CH3:27])[C:18]=2[CH:17]=1

참가 물질

6

반응물 4

HCID 7416NitrobenzeneHCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 668341732-(2-hydroxypropan-2-yl)-1H-indole-6-carbonitrile

생성물 1

HCID 668341058-Methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile수율 40.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

(Method 3) To nitrobenzene (5 ml) and aluminum chloride (400 mg, 3 mmol), 4-methoxybenzoyl chloride (400 mg, 2.3 mmol) was added. After stirring for 30 min at room temperature, 2-(1-hydroxy-1-methyl-ethyl)-1H-indole-6-carbonitrile (Compound AA6, 200 mg, 1 mmol) was added followed by stirring at room temperature for 3 hr. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (127 mg, 40%).

후처리

  1. stirringby stirring at room temperature for 3 hr
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe drying agent was removed by filtration
  5. customthe residues obtained
  6. concentrationafter concentration under reduced pressure
  7. customwere purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8362a13e30874b68abe42b0387790014
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440922B2

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