Homophthalic anhydride → 1,3(2H,4H)-isoquinolinedione

HRID 1081571Notes

Reaction equation

[C:1]1(=O)[O:7][C:5](=[O:6])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.C(=O)([O-])[O-].[NH4+:17].[NH4+]>>[C:1]1(=[O:7])[NH:17][C:5](=[O:6])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1

Participants

Reactant 2

HCID 12801Homophthalic anhydride

HCID 517111Ammonium Carbonate

Product 1

HCID 3494351,3(2H,4H)-isoquinolinedioneYield 95%

Conditions

Temperature: 280 °C

Procedure

Homophthalic anhydride (1.62 g, 10 mmol) and ammonium carbonate (1.61 g, 10 mmol) are ground in a mortar and then slowly heated to fusion at about 280° C. After 2 h, the reaction mixture is allowed to cool. The product is practically pure and needs no further treatment. Thus homophthalimide is obtained in 95% yield (153 mg).

Workup

temperatureto cool

Sources & evidence

ORD record: ord-1ba2c41f22b54ffc923bd718f11909f1
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05587385

Reaction notes

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