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

HRID 1637261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637261
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-56236f5626df490288eac5b1ef260539
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040331

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