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

HRID 1637261Notes

Reaction equation

HRID 1637261 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-56236f5626df490288eac5b1ef260539
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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