4-Nitrophenylhydrazine hydrochloride → Diethyl-6-nitro-1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate

HRID 373991Notes

Reaction equation

HRID 373991 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:3]1.Cl.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([NH:28]N)=[CH:24][CH:23]=1)([O-:21])=[O:20]>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[CH2:16]([O:15][C:13]([CH:4]1[CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][C:7]2[C:26]3[C:25](=[CH:24][CH:23]=[C:22]([N+:19]([O-:21])=[O:20])[CH:27]=3)[NH:28][C:2]=2[CH2:3]1)=[O:14])[CH3:17]

Participants

5

Reactant 2

HCID 54634014-Nitrophenylhydrazine hydrochlorideHCID 14062941Diethyl 4-oxocyclohexane-1,2-dicarboxylate

Product 1

HCID 19808689Diethyl-6-nitro-1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylateYield 21%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

To 50 ml of acetic acid were added 2.4 g of diethyl 4-oxocyclohexane-1,2-dicarboxylate, 3.0 g of zinc chloride and 1.9 g of 4-nitrophenylhydrazine hydrochloride. The mixture was refluxed for 4 hours. Then, acetic acid was removed by distillation under reduced pressure. To the residue were added 100 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 recrystallized from iso-propyl alcohol to obtain 750 mg (yield: 21%) of diethyl-6-nitro-1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customThen, acetic acid was removed by distillation under reduced pressure
  3. additionTo the residue were added 100 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 recrystallized from iso-propyl alcohol

Sources & evidence

ORD record
ord-9a7672fa7e114c8a840c9651d059123d
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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