Ethyl-alpha-carbethoxy-4-methylamino-2-nitrodihydrocinnamate → 7-Methylamino-3-carbethoxy-3,4-dihydro-2-quinolone

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Reaction Steps

A mixture of 2.6 g of the diester (4), of 10% Pd on charcoal and 75 mL of dioxane were shaken under 50 psi of hydrogen for 17 hours at 50° C. The catalyst was removed by filtering through Celite and the solvent was removed. The residue was chromatographed on 200 g of silica gel eluting with 3:17 (v/v) acetone: CH2Cl2. Fractions 75-120 (17 mL/fraction) were combined and concentrated to yield 0.5 g of a white powder. Recrystallization from MeOH-H2O produced an analytical sample, m.p. 171°-172° C.

Provenance & Evidence