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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → N-benzylcarbazole-3,4-dicarboximide

HRID 373988
Notes
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Reaction equation

HRID 373988 reaction equation
[CH2:1]([N:8]1[C:24](=[O:25])[CH:23]2[CH:11]([CH2:12][CH2:13][C:14]3[NH:15][C:16]4[C:21]([C:22]=32)=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:1]([N:8]1[C:24](=[O:25])[C:23]2[C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]=3[CH:13]=[CH:12][C:11]=2[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11430Potassium CarbonateHCID 2865034N-benzyl-1,2,3,4-tetrahydrocarbazole-3,4-dicarboximide

Product 1

HCID 19808688N-benzylcarbazole-3,4-dicarboximideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

150 mg of N-benzyl-1,2,3,4-tetrahydrocarbazole-3,4-dicarboximide was dissolved in 5 ml of methylene chloride. To this solution was added 220 mg of 2,3-dichloro-5,6-dicyano-p-benzoquinone (abbreviated to hereinafter as DDQ). The mixture was stirred at room temperature for 10 minutes. Then, thereto were added 20 ml of methylene chloride and 10 ml of an aqueous 10% potassium carbonate solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from n-propanol to obtain 120 mg (yield: 81%) of N-benzylcarbazole-3,4-dicarboximide as orange needles.

Workup

  1. customThe organic layer was separated
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-e3e7df8bc67b4d75846b73d1b43818de
Source dataset
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05166204

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes