Water → 2,7,9-Trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate

HRID 517623

Reaktionsgleichung

[CH3:1][O:2][C:3]([C:5]1[NH:27][C:8]2=[C:9]3[C:14](=[C:15]([O:17]C)[CH:16]=[C:7]2[CH:6]=1)[N:13]=[C:12]([C:19]([O:21][CH3:22])=[O:20])[CH:11]=[C:10]3[C:23]([O:25][CH3:26])=[O:24])=[O:4].[OH2:28]>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[NH:27][C:8]2[C:9]3[C:10]([C:23]([O:25][CH3:26])=[O:24])=[CH:11][C:12]([C:19]([O:21][CH3:22])=[O:20])=[N:13][C:14]=3[C:15](=[O:17])[C:16](=[O:28])[C:7]=2[CH:6]=1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

To a suspension of 5-methoxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester (about 250 g, 0.67 mol) in acetonitrile (ACN) (about 7.5 L), a solution of ceric ammonium nitrate (about 1.83 kg, 3.35 mol) in about 2.25 L of water is added over a period of about 30 minutes at about −5° C. The reaction mixture is stirred at about −5° C. over a period of about 1.5 hours. Thereafter, resulting reaction mass is filtered, washed with water and dried to obtain the product [4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester] as a bright orange solid (about 145 g, 58%). 1H NMR (DMSO-d6, 300 MHz): 3.90 (s, 3H), 3.97 (s, 3H), 4.05 (s, 3H), 7.29 (d, J=1.8 Hz, 1H), 8.56 (s, 1H), 12.52 (s, 1H); LC-MS (ESI): 373.0 (M-H).

Aufarbeitung

customThereafter, resulting
customreaction mass
filtrationis filtered
washwashed with water
customdried

Quellen und Nachweise

ORD-Eintrag: ord-126843f4a9de43d9b1bcef5ad684e4a5
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115128B2

Verknüpfte Notizen

Wird geladen…