Water → 1-Methoxycarbonylmethyl-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

HRID 1637261노트

반응식

HRID 1637261 반응식
[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:18](=[O:19])[CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25].O>CN(C)C=O.C(OCC)(=O)C>[CH3:27][O:26][C:24]([CH2:23][N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18](=[O:19])[CH2:17][CH2:16][C:15]([C:14]=23)=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:25]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 193483682-Phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one

생성물 1

HCID 193483211-Methoxycarbonylmethyl-2-phenyl-1,3,4,5-tetrahydrobenz[cd]indol-5-one수율 90%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 8857Ethyl Acetate용매

실험 절차

A solution of the compound (1.37 g) obtained in Example 41 in anhydrous dimethylformamide (DMF; 60 ml) was added to a suspension of sodium hydride (60% dispersion in oil; 0.30 g) in DMF(10 ml) at room temperature. After stirring for 15 minutes, a solution of methyl bromoacetate (0.72 ml) in DMF (10 ml) was added to the reaction mixture. The reaction mixture was stirred for 10 minutes at room temperature, followed by addition of water and extraction with three portions of ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from ethyl acetate to yield 1.58 g (90%) of the titled compound as a yellow powder.

후처리

  1. stirringThe reaction mixture was stirred for 10 minutes at room temperature
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-56236f5626df490288eac5b1ef260539
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06040331

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