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

HRID 373991노트

반응식

HRID 373991 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a7672fa7e114c8a840c9651d059123d
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166204

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