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

HRID 499505Notes

Reaction equation

HRID 499505 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-95363a66849c409b8ab916f065f7ebb8
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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