Triphenylphosphine → 1,2,3,6-Tetrahydro-1,3-dioxo-4-phenylpyrrolo[3,4-c]carbazole

HRID 1165794

Reaktionsgleichung

Reaktionsgleichung von HRID 1165794
[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-])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1C(C)=CC(C)=CC=1C>[O:26]=[C:12]1[C:11]2[C:10]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH:1][C:18]=3[CH:17]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]=2[C:14](=[O:25])[NH:13]1

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 146772851,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole

Produkt 1

HCID 146772861,2,3,6-Tetrahydro-1,3-dioxo-4-phenylpyrrolo[3,4-c]carbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 79532,4,6-TrimethylpyridineLösungsmittel

Versuchsvorschrift

3.5 g (10.2 mmole) 1,3-dihydro-4-(2-nitrophenyl)-1,3-dioxo-7-phenyl-2H-isoindole and 9.5 g (36.2 mmole) triphenylphosphine are heated under reflux for 16 hours in 100 ml 2,4,6-collidine. The solvent is distilled off in a vacuum and the residue chromatographed on silica gel with toluene/ethyl acetate 3:1. The fraction with the Rf 0.3 is isolated and recrystallized from cyclohexane/acetone. One obtains 1,2,3,6-tetrahydro-1,3-dioxo-4-phenylpyrrolo[3,4-c]carbazole in the form of yellow crystals of the mp 262°-264° C.

Aufarbeitung

  1. distillationThe solvent is distilled off in a vacuum
  2. customthe residue chromatographed on silica gel with toluene/ethyl acetate 3:1
  3. customThe fraction with the Rf 0.3 is isolated
  4. customrecrystallized from cyclohexane/acetone

Quellen und Nachweise

ORD-Eintrag
ord-ae31a70b6376428e8827103be40cd4e5
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04912107

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