Dichloromethane → 7-Chloro-3-(isoquinolin-1-ylaminomethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

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Reaction Steps

In a 10 mL round-bottomed flask, methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylate (50 mg, 0.123 mmol) was combined with methylene chloride (5 mL) to give a colorless solution. To this solution, N,N-diisopropylethylamine and 1-aminoisoquinoline were added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into 25 mL H2O and extracted with ethyl acetate (1×25 mL). The organic layer was washed with 1 M HCl (1×10 mL), saturated aqueous NaHCO3 (1×10 mL), and H2O (1×10 mL). The organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 4 g, 5% to 40% ethyl acetate in hexanes), giving 7-chloro-3-(isoquinolin-1-ylaminomethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (4 mg, 7%). MS calcd. for C27H20ClN3O3 [(M+H)+] 470.1, obsd. 470.9.

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