반응 #3229

반응 방정식

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

acetic acid

→

title compound

수율 75.3%

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

수율 75.3%

용매

ethanol

반응 조건

후처리

1. 1
   온도was refluxed for 20 hr under a nitrogen atmosphere
2. 2
   온도The reaction mixture was cooled
3. 3
   여과filtered
4. 4
   농축the filtrate was concentrated
5. 5
   기타The dark residue was chromatographed (eluant: methylene chloride/methanol; 98/2) over silical gel

실험 절차

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).

출처