Ethanol → 1,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

HRID 1165795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165795
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH:18]=[CH:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]2[CH:11]1[C:12](=[O:26])[NH:13][C:14]2=[O:25])([O-:3])=[O:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(O)C>C(C1C=CC=CC=1)(C)(C)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:15]2[C:11]=1[C:12](=[O:26])[NH:13][C:14]2=[O:25])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 146772841,3,3a,4,7,7a-hexahydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

Produkt 1

HCID 146772851,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7366Tert-ButylbenzeneLösungsmittel

Versuchsvorschrift

5.5 g (15.8 mmole) 1,3,3a,4,7,7a-hexahydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole and 9.1 g (40.1 mmole) 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) are heated under reflux for 16 hours in 100 ml t-butylbenzene. The solvent is removed in a vacuum and the residue chromatographed on silica gel with toluene/ethyl acetate 3:1. The fraction with the Rf of 0.4 is isolated, stirred with a little hot ethanol, and the crystals formed after cooling are filtered off. After recrystallization from ethyl acetate, one obtains 1,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole in the form of colorless crystals of the mp 224°-226° C.

Aufarbeitung

  1. customThe solvent is removed in a vacuum
  2. customthe residue chromatographed on silica gel with toluene/ethyl acetate 3:1
  3. customThe fraction with the Rf of 0.4 is isolated
  4. customthe crystals formed
  5. temperatureafter cooling
  6. filtrationare filtered off
  7. customAfter recrystallization from ethyl acetate, one

Quellen und Nachweise

ORD-Eintrag
ord-ac6d175fc7f444c19a9bffb6255a90b8
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04912107

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