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

HRID 2427255Notes

Reaction equation

HRID 2427255 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 70,889.102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mix cyclopentenone (100 g, 1.2 mol) and phthalimide (170 g, 1.2 mmol) in MeOH (900 mL) and stir for 18 h at ambient temperature. Stir vigorously with a mechanical stirrer and add 2 M aqueous Na2CO3 (80 mL). After approximately 2 h, a thick white precipitate will form. Stir at room temperature for 48 h. Collect the white solid by vacuum filtration and rinse with methanol. Suspend the solid in water (300 mL) and stir for 3 h. Collect the solid and dry in a vacuum oven at 40° C. overnight to give 195 g (71%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.85-7.77 (m, 4H), 4.90 (m, 1H), 2.67 (ddd, 1H, J=18.5, 6.2, 1.3 Hz), 2.54 (dd, 1H, J=18.5, 9.2 Hz), 2.45 (m, 1H), 2.32-2.21 (m, 3H); MS (m/z): 230 (M+1, weak).

Workup

  1. stirringStir vigorously with a mechanical stirrer
  2. waitAfter approximately 2 h
  3. customa thick white precipitate will form
  4. stirringStir at room temperature for 48 h
  5. customCollect the white solid
  6. filtrationby vacuum filtration
  7. washrinse with methanol
  8. stirringstir for 3 h
  9. customCollect the solid
  10. customdry in a vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-225cd0315adb40d3aa89539bd9d9f57c
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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