3-(4-nitro-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione → 3-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione

Participants

Reaction Steps

To a solution of 5,7-dichloro-3-methyl-3-(4-nitro-phenyl)-1H-quinoline-2,4-dione (1.0 g, 2.74 mmol) in methanol (30 mL) was added SnCl2-2H2O (1.85 g, 8.22 mmol). The resulting solution was stirred at reflux temperature overnight. After the reaction was completed, a yellow residue was obtained after evaporating solvent under reduced pressure. The residue was then diluted with 1N HCl solution (200 mL), and extracted with ethyl acetate (200 mL×3). The combined organic layer was washed with brine (200 ml×2) and water (200 mL×2) and dried over magnesium sulfate anhydride. After evaporation of the solvent, the objective compound (0.61 g, 66%) was obtained as pale yellow solid by purifying the residue with flash column chromatography (n-hexane:ethyl acetate=4:1): 1H NMR (200 MHz, CDCl3) δ 1.68 (s, 3H, CH3), 3.68 (br s, 2H, NH2), 6.58 (d, J=8.8 Hz, 2H, ArH), 6.73 (d, J=1.8 Hz, 1H, ArH), 6.96 (d, J=8.8 Hz, 2H, ArH), 7.08 (d, J=1.8 Hz, 1H, ArH), 8.21 (br s, 1H, NH); MS(EI) m/e 335 [M++1].

Provenance & Evidence