Homophthalic anhydride → 2-(4-Methoxy-benzyl)-4H-isoquinoline-1,3-dione

HRID 2228965Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[C:11]1(=O)[O:17][C:15](=[O:16])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]2[CH2:12]1>O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:8]2[C:11](=[O:17])[CH2:12][C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:16])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 180 °C

Procedure

4-Methoxybenzylamine (8.3 g) was added to homophthalic anhydride (8.1 g). The mixture was stirred at 180° C. overnight. Water was added to the reaction solution. The mixture was then extracted with ethyl acetate. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:2) to give 2-(4-methoxybenzyl)-4H-isoquinoline-1,3-dione (11.8 g).

Workup

extractionThe mixture was then extracted with ethyl acetate
dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under the reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:2)

Sources & evidence

ORD record: ord-35ebf3a09291403da9ebcdb595321066
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417362B1

Reaction notes

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