Reaktion #3229

Reaktionsgleichung

diethyl 4-hydroxy-6-nitroquinoline-2,3-dicarboxylate

acetic acid

→

title compound

Ausbeute 75.3%

Diethyl 6-amino-4-hydroxyquinoline-2,3-dicarboxylate

Ausbeute 75.3%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 20 hr under a nitrogen atmosphere
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Filtrationfiltered
4. 4
   Einengenthe filtrate was concentrated
5. 5
   SonstigeThe dark residue was chromatographed (eluant: methylene chloride/methanol; 98/2) over silical gel

Vorschrift

A stirred mixture of diethyl 4-hydroxy-6-nitroquinoline-2,3-dicarboxylate (4.4 g, 13 mM), powdered iron (6.6 g, 118 mM) and glacial acetic acid (18.5 g, 307 mM) in ethanol (80 mL) was refluxed for 20 hr under a nitrogen atmosphere. The reaction mixture was cooled and filtered and the filtrate was concentrated. The dark residue was chromatographed (eluant: methylene chloride/methanol; 98/2) over silical gel to provide (3.01 g, 75.3%) the title compound as light orange crystals, mp 219°-221° C.; MS(CI): 305 (M+H).

Quelle