Phthalic Anhydride → 1H-Isoindole-1,3(2H)-dione, 2-(2-nitrophenyl)-

HRID 1836428

Reaktionsgleichung

Reaktionsgleichung von HRID 1836428
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12>C(O)(=O)C>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[N:6]1[C:14](=[O:15])[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]1=[O:16])([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 6811Phthalic AnhydrideHCID 69462-Nitroaniline

Produkt 1

HCID 1013131H-Isoindole-1,3(2H)-dione, 2-(2-nitrophenyl)-Ausbeute 121,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a mixture of 2-nitroaniline (1 g, 7.23 mmol) in acetic acid (5 mL) was added phthalic anhydride (1.29 g, 8.7 mmol) followed by stirring at ambient temperature for 16 h. The mixture was then heated at reflux for 20 h. Upon cooling, a yellow precipitate formed and was collected by filtration. The filtrate was washed with acetic acid and was dried under a under a stream of air to give 2.35 g (100%) of 2-(2-nitrophenyl)isoindole-1,3-dione: 1H NMR (300 MHz, DMSO-d6) δ8 8.21 (m, 1H), 8.02-7.95 (m, 5H), 7.77 (m, 2H).

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 20 h
  3. temperatureUpon cooling
  4. customa yellow precipitate formed
  5. filtrationwas collected by filtration
  6. washThe filtrate was washed with acetic acid
  7. customwas dried under a under a stream of air

Quellen und Nachweise

ORD-Eintrag
ord-d2682b66907745169d4cc59f63292860
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777432B1

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