Sodium Acetate → 3-Phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole

HRID 128749Notes

Reaction equation

HRID 128749 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1)#[N:3].C([O-])(=O)C.[Na+].[C:17]1(=[O:34])[N:21]([CH:22]2[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]2)[C:20](=[O:29])[C:19]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:18]12>C(O)(=O)C>[C:20]1(=[O:29])[N:21]([CH:22]2[CH2:23][C:24]3[C:8]4[C:7](=[CH:6][CH:5]=[C:4]([C:2]#[N:3])[CH:9]=4)[NH:10][C:25]=3[CH2:26][CH2:27]2)[C:17](=[O:34])[C:18]2=[CH:33][CH:32]=[CH:31][CH:30]=[C:19]12

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dioneHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 189442603-Phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Cyanophenyl hydrazine hydrochloride (4.41 g, 0.026 mole) was dissolved in acetic acid (100 ml) and sodium acetate (2 g) was added. 4-Phthalimido cyclohexanone (6.4 g, 0.026 mole) was added and the mixture heated under reflux overnight. The solvent was removed in vacuo and the residue triturated with methanol to give 3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole as a beige solid, (5.3 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated with methanol

Sources & evidence

ORD record
ord-e9c913666c4d4d3cb40e24a6635be682
Source dataset
uspto-grants-1995_11
Patent number
US05464864

Reaction notes

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