Water → 1-Pentyl-1H-indole-2,3-dione

HRID 2393617Notes

Reaction equation

HRID 2393617 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]1=[O:13].[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH3:18].O>CN(C)C=O>[CH2:14]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]1=[O:13])[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7054IsatinHCID 80571-BromopentaneHCID 24758Sodium hydride

Product 1

HCID 15810921-Pentyl-1H-indole-2,3-dioneYield 88.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 270 mg of sodium hydride was added to 1.00 g of 2,3-dihydro-1H-indol-2,3-dione in dimethylformamide at room temperature. After the reaction mixture was stirred at room temperature for 10 minutes, 5 ml of a dimethylformamide solution of 2.10 g of pentyl bromide was added dropwise thereto. After the reaction mixture was stirred at room temperature for 20 minutes, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After the extract was washed with water and dried, the solvent was removed by evaporation. The residue was purified by silica gel column chromatography [ethyl acetate-hexane (1:5)] to afford 1.31 g of 2,3-dihydro-1-pentyl-1H-indol-2,3-dione as orange crystals. Melting point: 50° to 51° C.

Workup

  1. stirringAfter the reaction mixture was stirred at room temperature for 20 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washAfter the extract was washed with water
  4. customdried
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by silica gel column chromatography [ethyl acetate-hexane (1:5)]

Sources & evidence

ORD record
ord-95871e1069c147ec82475c80044b4694
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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