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

HRID 373991ノート

反応式

HRID 373991 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9a7672fa7e114c8a840c9651d059123d
出典データセット
uspto-grants-1992_11
特許番号
US05166204

反応ノート

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