N-Phenylphthalimide → 2,3-Dihydro-2-phenyl-1H-isoindol-1-one

HRID 261522Notes

Reaction equation

HRID 261522 reaction equation
[C:1]1([N:7]2[C:11](=O)[C:10]3=[CH:13][CH:14]=[CH:15][CH:16]=[C:9]3[C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Zn].C(O)(=O)C>[CH2:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:17])[C:9]2[C:10]1=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

4

Reactant 1

HCID 68215N-Phenylphthalimide

Product 1

HCID 970352,3-Dihydro-2-phenyl-1H-isoindol-1-oneYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-phenylphthalimide (100 g), zinc powder (147 g) and acetic acid (700 ml) is heated under reflux for 5.5 hours with stirring. After cooling, the mixture is filtered and the insoluble solid is washed with hot acetic acid (100 ml). The combined filtrate and washings are concentrated to give crystal (72 g, 78%). Recrystallization from benzene gives colorless scales. Melting point: 166° to 167° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5.5 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. washthe insoluble solid is washed with hot acetic acid (100 ml)
  6. concentrationThe combined filtrate and washings are concentrated

Sources & evidence

ORD record
ord-45d7bbf4da3a4ad8808211dd6c270b8c
Source dataset
uspto-grants-1979_08
Patent number
US04166125

Reaction notes

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