Acetic Acid → 9-Benzoyl-1,2,3,4-tetrahydrocarbazole-3,3-dicarboxylic acid

HRID 1605082Notes

Reaction equation

HRID 1605082 reaction equation
Cl.[C:2]([N:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)N)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:18]1[C:23](=O)[CH2:22][CH2:21][C:20]([C:28]([OH:30])=[O:29])([C:25]([OH:27])=[O:26])[CH2:19]1.C(O)(=O)C>O>[C:2]([N:10]1[C:23]2[CH2:22][CH2:21][C:20]([C:28]([OH:30])=[O:29])([C:25]([OH:27])=[O:26])[CH2:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 121972221-Benzoyl-1-phenylhydrazine hydrochlorideHCID 132208344-Oxocyclohexane-1,1-dicarboxylic acid

Product 1

HCID 215483979-Benzoyl-1,2,3,4-tetrahydrocarbazole-3,3-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Benzoyl-1-phenylhydrazine hydrochloride (5 g.) and 4 g. of cyclohexanone-4,4-dicarboxylic acid in 10 ml. of glacial acetic acid were heated at 60°-70°C. for thirty minutes. The mixture was diluted with water and the resulting solid was collected by filtration and washed with water to give 7.1 g. of the title compound; m.p. 160°C. (acetone and hexane).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. customto give 7.1 g

Sources & evidence

ORD record
ord-63db3498520749abbf7d89a08047fd7a
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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