Reaktion #11141

ord-9646ed85d1e945ff98b8b534569f0755

Reaktionsgleichung

COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O
4-(3,5-dinitrophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
Cl.c1cc[nH+]cc1
pyridinium hydrochloride
→
O=C1NC(=O)c2c1c(-c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)cc1[nH]c3ccc(O)cc3c21
4-(3,5-Dinitrophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
Ausbeute 57.0%

Edukte

COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O
4-(3,5-dinitrophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
Cl.c1cc[nH+]cc1
pyridinium hydrochloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeprepared

Vorschrift

The reaction of 4-(3,5-dinitrophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=3,5-dinitrophenyl, R10═H) (42) prepared as described in example 48 with pyridinium hydrochloride according to the proceedure described in example 81 gave 4-(3,5-Dinitrophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=3,5-dinitrophenyl, R10═H) (43) in a 57% yield as an orange powder, mp>330° C. 1H NMR δ [(CD3)2SO] 11.94 (br s, 1H), 11.18 (br s, 1H), 9.32 (br s, 1H), 8.91 (s, 3H), 8.35 (d, J=2.3 Hz, 1H), 7.83 (s, 1H), 7.49 (d, J=8.7 Hz, 1H), 7.11 (dd, J=8.7, 2.3 Hz, 1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094798B1uspto-grants-2006_08