Phthalimide → 2-(3-Oxocyclopentyl)-1H-isoindole-1,3(2H)-dione

HRID 2404387Notes

Reaction equation

HRID 2404387 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.C(=O)([O-])[O-].[Na+].[Na+]>CO>[O:6]=[C:1]1[CH2:5][CH2:4][CH:3]([N:11]2[C:7](=[O:17])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10]2=[O:12])[CH2:2]1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 10340Sodium CarbonateHCID 135882-Cyclopenten-1-one

Product 1

HCID 545940982-(3-Oxocyclopentyl)-1H-isoindole-1,3(2H)-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of methanol (88 mL), 2-cyclopenten-1-one (10.2 mL, 122 mmol), and phthalimide (17.9 g, 122 mmol) was stirred at ambient temperature and sodium carbonate (2M in water, 7.92 mL, 15.8 mmol) was added. After 22 hours, the thick white slurry was filtered and washed with MeOH (100 mL). Water (100 mL) was added to the wet cake, stirred for 1 hour, and filtered. The solid was washed with water (50 mL) and dried in a vacuum oven at 50° C. for 14 hours to provide the title compound (17.8 g, 78.0 mmol, 64% yield). MS (DCI) M/Z 247 [M+NH4]+.

Workup

  1. filtrationthe thick white slurry was filtered
  2. washwashed with MeOH (100 mL)
  3. additionWater (100 mL) was added to the wet cake
  4. filtrationfiltered
  5. washThe solid was washed with water (50 mL)
  6. customdried in a vacuum oven at 50° C. for 14 hours

Sources & evidence

ORD record
ord-925b58ace63d4b579429cb0d6ea4574c
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

Loading…