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

HRID 373991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373991
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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9a7672fa7e114c8a840c9651d059123d
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166204

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