Phthalic Anhydride → 2-(4-Pyridinylmethyl)-1H-isoindole-1,3(2H)-dione

HRID 374453Notes

Reaction equation

HRID 374453 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[N:12]1[CH:17]=[CH:16][C:15]([CH2:18][NH2:19])=[CH:14][CH:13]=1>CN(C)C=O>[N:12]1[CH:17]=[CH:16][C:15]([CH2:18][N:19]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 773174-Pyridinemethanamine

Product 1

HCID 27316422-(4-Pyridinylmethyl)-1H-isoindole-1,3(2H)-dioneYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 74 g (0.5 mole) of phthalic anhydride, 60 g (0.56 mole) of 4-pyridinemethylamine and 200 mL of dimethylformamide was heated under reflux for 2 hours. The cooled mixture was filtered and the solids were washed with ether and dried to give 85.1 g of 2-(4-pyridinylmethyl)-1H-isoindole-1,3(2H)-dione, m.p. 164°-165°. Another 24.0 g was obtained by crystallization of the concentrated mother liquors from dimethylformamide. Combined yield: 99.1 g (83%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe cooled mixture was filtered
  4. washthe solids were washed with ether
  5. customdried

Sources & evidence

ORD record
ord-b93ae8285d414c7cb407df71a525b2c6
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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