Ethyl Acetate → 2-(1-Methyl-2-oxobutyl)-1H-isoindole-1,3(2H)-dione

HRID 1424913Notes

Reaction equation

HRID 1424913 reaction equation
Br[CH:2]([C:4](=[O:7])[CH2:5][CH3:6])[CH3:3].[C:8]1(=[O:18])[NH:12][C:11](=[O:13])[C:10]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:9]12.[K].C(OCC)(=O)C>CN(C=O)C>[CH3:3][CH:2]([N:12]1[C:8](=[O:18])[C:9]2[C:10](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:11]1=[O:13])[C:4](=[O:7])[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 5450922-Bromo-3-pentanoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 648658632-(1-Methyl-2-oxobutyl)-1H-isoindole-1,3(2H)-dioneYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-pentan-3-one obtained in Example (15a) (8.47 g, 35.57 mmol) was dissolved in DMF (120 mL). Potassium phthalimide (6.9 g, 37.25 mmol) was added, and the mixture was stirred at room temperature for 10 hours. Ethyl acetate was added to the reaction solution, and the organic layer was washed with 1 N hydrochloric acid and brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was washed with hexane to obtain 6.5 g of the title compound as a white solid (79%).

Workup

  1. washthe organic layer was washed with 1 N hydrochloric acid and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentration under reduced pressure
  4. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-a94bdddd9cef4b3e955806519137f31f
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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