Potassium Carbonate → 2-(3-Hydroxypropyl)isoindoline-1,3-dione

HRID 482006Notes

Reaction equation

HRID 482006 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.[K].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:6]1(=[O:16])[N:10]([CH2:2][CH2:3][CH2:4][OH:5])[C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 24194345Phthalimide potassium salt

Product 1

HCID 701602-(3-Hydroxypropyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-Bromopropanol (4.0 g, 28.78 mmol), potassium phthalimide (8.0 g, 43.17 mmol) and potassium carbonate (4.0 g, 28.78 mmol) were added to 20 mL DMF. The reaction mixture was stirred at 70° C. for 4 hours, quenched with water and extracted with ethyl acetate. The organic layer was washed with water, saturated NaCl solution and evaporated in vacuo to a solid which was crystallized in ethyl acetate (3.5 g, 67%).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated NaCl solution
  4. customevaporated in vacuo to a solid which
  5. customwas crystallized in ethyl acetate (3.5 g, 67%)

Sources & evidence

ORD record
ord-766fc037d667409a95f408ee865d8c47
Source dataset
uspto-grants-1998_08
Patent number
US05792776

Reaction notes

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