1-Methylpiperazine → 3-(4-amino-phenyl)-5-chloro-3-methyl-7-(4-methyl-piperazine-1-yl)-1H-quinoline-2,4-dione

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Reaction Steps

A mixture of 3-(4-amino-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione (0.1 g, 0.30 mmol) and 1-methylpiperazine (36 mL, 0.36 mmol) in dry pyridine (5.0 mL) was heated at reflux temperature overnight. After evaporation of the solvent in vacuo, the residue was diluted with water (50 mL), and resulting suspension was extracted with ethyl acetate (50 mL×3). The organic layer was washed with brine (50 mL×2) and dried over anhydrous MgSO4 concentrated under reduced pressure. The pure objective compound (87 mg, 73%) was obtained as yellow solid by a flash column chromatography (CH2Cl2:MeOH=20:1): 1H NMR (200 MHz, CDCl3) δ 1.78 (s, 3H, CH3) 2.35 (s, 3H, NCH3), 2.43-2.67 (m, 4H, NCH2), 2.90-2.95 (m, 4H, NCH2), 3.67 (br s, 2H, NH2), 6.38 (d, J=1.8 Hz, 1H, ArH), 6.54-6.61 (m, 3H, ArH), 7.04 (d, J=8.6 Hz, 2H, ArH), 8.44 (br s, 1H, NH).

Provenance & Evidence