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

HRID 2275066Notes

Reaction equation

HRID 2275066 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-674a4c9ee07d4595a76e13407ed2d047
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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