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

HRID 1532181Notes

Reaction equation

HRID 1532181 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-13ec53497ae847a0a66870047c8e9ed2
Source dataset
uspto-grants-2001_03
Patent number
US06201016B1

Reaction notes

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