(3,5-Dichlorophenyl)hydrazine monohydrochloride → N-benzyl-5,7-dichloro-1,2,3,4-tetrahydrocarbazole-3,4-dicarboximide

HRID 373987Notes

Reaction equation

HRID 373987 reaction equation
[CH2:1]([N:8]1[C:18](=[O:19])[CH:12]2[CH2:13][C:14](=O)[CH2:15][CH2:16][CH:11]2[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:21][C:22]1[CH:23]=[C:24]([NH:29]N)[CH:25]=[C:26]([Cl:28])[CH:27]=1>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[CH2:1]([N:8]1[C:18](=[O:19])[CH:12]2[CH:11]([CH2:16][CH2:15][C:14]3[NH:29][C:24]4[C:23]([C:13]=32)=[C:22]([Cl:21])[CH:27]=[C:26]([Cl:28])[CH:25]=4)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([N:8]1[C:18](=[O:19])[CH:12]2[CH:11]([CH2:16][C:15]3[NH:29][C:24]4[C:23]([C:14]=3[CH2:13]2)=[C:22]([Cl:21])[CH:27]=[C:26]([Cl:28])[CH:25]=4)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 2723913(3,5-Dichlorophenyl)hydrazine monohydrochlorideHCID 28618042-benzyltetrahydro-1H-isoindole-1,3,5(2H,4H)-trione

Product 2

HCID 19808693N-benzyl-5,7-dichloro-1,2,3,4-tetrahydrocarbazole-3,4-dicarboximideYield 28%HCID 19808797N-benzyl-5,7-dichloro-1,2,3,4-tetrahydrocarbazole-2,3-dicarboximideYield 17%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

To 30 ml of acetic acid were added 1.54 g of N-benzyl-4-oxocyclohexane-1,2-dicarboximide, 3.0 g of zinc chloride and 1.54 g of 3,5-dichlorophenylhydrazine hydrochloride. The mixture was refluxed for 2 hours. Acetic acid was removed by distillation under reduced pressure. To the residue were added 150 ml of ethyl acetate and 50 ml of water. The organic layer was separated, washed with diluted hydrochloric acid, an aqueous saturated sodium chloride solution, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=30/1 to 20/1) to obtain 670 mg (yield: 28%) of N-benzyl-5,7-dichloro-1,2,3,4-tetrahydrocarbazole-3,4-dicarboximide [IR (KBr) cm-1 : 3320, 1770, 1695] and 400 mg (yield: 17%) of N-benzyl-5,7-dichloro-1,2,3,4-tetrahydrocarbazole-2,3-dicarboximide [IR (KBr) cm-1 : 3310, 1765, 1690], both as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customAcetic acid was removed by distillation under reduced pressure
  3. additionTo the residue were added 150 ml of ethyl acetate and 50 ml of water
  4. customThe organic layer was separated
  5. washwashed with diluted hydrochloric acid
  6. dry with materialan aqueous saturated sodium chloride solution, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=30/1 to 20/1)

Sources & evidence

ORD record
ord-7677c2cc31434aa5a14fcdbb6d1c44b7
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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