Sulfuric Acid → Diethyl 1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate

HRID 373990노트

반응식

HRID 373990 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.S(=O)(=O)(O)O.[C:23]1([NH:29]N)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.C(O)C>[CH2:6]1[C:7]2[NH:29][C:23]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:2]=2[CH2:3][CH:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 7516PhenylhydrazineHCID 516892Sodium BicarbonateHCID 14062941Diethyl 4-oxocyclohexane-1,2-dicarboxylate

생성물 1

HCID 19808697Diethyl 1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate수율 59.4%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To 20 ml of ethanol were added 2.66 g of diethyl 4-oxocyclohexane-1,2-dicarboxylate, 2.45 g of concentrated sulfuric acid and 1.08 g of phenylhydrazine. The mixture was refluxed for 2 hours and then cooled to room temperature. Thereto were added 50 ml of ethyl acetate and 50 ml of water. The mixture was adjusted to pH 7.5 with an aqueous saturated sodium hydrogencarbonate solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethanol to obtain 1.87 g (yield: 59%) of diethyl 1,2,3,4-tetrahydrocarbazole-2,3-dicarboxylate as colorless needles.

후처리

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe organic layer was separated
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customThe residue was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-754ae980b0c441478053da60818f18c9
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166204

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