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

HRID 1637261ノート

反応式

HRID 1637261 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒3 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-56236f5626df490288eac5b1ef260539
出典データセット
uspto-grants-2000_03
特許番号
US06040331

反応ノート

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