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

HRID 748323Notes

Reaction equation

HRID 748323 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[C:9]1(=O)[O:14][C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:1]1[C:12](=[O:13])[C:11]2[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]1=[O:14]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 195092-Pyridinemethanamine

Product 1

HCID 6172022-(2-Pyridinylmethyl)-1H-isoindole-1,3(2H)-dioneYield 86.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Aminomethylpyridine (4.0 g, 37 mmol) and phthalic anhydride (5.5 g, 37 mmol) were dissolved in toluene (100 ml), and triethylamine (3.7 g, 36 mmol) was added thereto. The mixture was refluxed for 3 hrs. The solvent was evaporated, and the residue was recrystallized from hexane-ethanol to give the titled compound (7.6 g, 86%).

Workup

  1. temperatureThe mixture was refluxed for 3 hrs
  2. customThe solvent was evaporated
  3. customthe residue was recrystallized from hexane-ethanol

Sources & evidence

ORD record
ord-bdc3dae446a34f078eb7eddc0216d03c
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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