Naphtho(2,3-c)furan-1,3-dione → N-(4-Methoxyphenyl)-2-(1,3-dihydro-1,3-dioxo-2H-benz[f]isoindol-2-yl)benzamide

HRID 427553

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[NH2:17])=[CH:5][CH:4]=1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]2[C:29]([O:31][C:32](=O)[C:20]=12)=[O:30]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[C:32](=[O:31])[C:20]3[CH:19]=[C:28]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]4=[CH:22][C:21]=3[C:29]2=[O:30])=[CH:7][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A pressure tube was charged with N-(4-methoxyphenyl)-2-aminobenzamide (500 mg, 2.07 mmol), 2,3-napthalenedicarboxylic anhydride (409 mg, 2.07 mmol), and tetrahydrofuran (10 mL). The resultant slurry was then placed in a bath heated to 110° C. for 16 h. After cooling to ambient temperature and concentration to ½ of the solution volume, the product was triturated with 50% hexanes/50% ethyl acetate and the resulting solid collected by filtration. Recrystallization from hexanes/ethyl acetate yielded 476 mg (55%) of the title compound.

Aufarbeitung

customThe resultant slurry was then placed in a bath
temperatureAfter cooling to ambient temperature
concentrationconcentration
customthe product was triturated with 50% hexanes/50% ethyl acetate
filtrationthe resulting solid collected by filtration
customRecrystallization from hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-5ad3e3a8c2e546039247aca481dbfca3
Quelldatensatz: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06313122B1

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