Water → 2-(4-methylpentyl)-1H-isoindole-1,3(2H)-dione

HRID 471802Notes

Reaction equation

HRID 471802 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].[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(Cl)(Cl)Cl.O>CN(C=O)C>[CH3:6][CH:5]([CH3:7])[CH2:4][CH2:3][CH2:2][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]

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 69385Pentane, 1-bromo-4-methyl-HCID 24194345Phthalimide potassium salt

Product 1

HCID 187402132-(4-methylpentyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromo-4-methylpentane (5.0 g, 0.030 mol) in DMF (20 mL) was added potassium phthalimide (5.9 g, 0.032 mol) in one portion at room temperature. After stirring at room temperature of 1 hr, the mixture was heated at 55° C. for 16 hr. Chloroform (30 mL) was added to the reaction mixture and the resulting mixture was poured into water (100 mL). The aqueous phase was extracted with chloroform and the combined organic phase was washed with 0.25 M NaOH (aq) and water. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give 2-(4-methylpentyl)-1H-isoindole-1,3(2H)-dione as a pale yellow oil. (M+H) 232, 2.80 min. (LC/MS method A).

Workup

  1. temperaturethe mixture was heated at 55° C. for 16 hr
  2. extractionThe aqueous phase was extracted with chloroform
  3. washthe combined organic phase was washed with 0.25 M NaOH (aq) and water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a44ec3c938254d83aea220bef978a69d
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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