Chloroacetyl chloride → 5-(Chloroacetyl)-8-methoxy-1-methylquinolin-2(1H)-one

Participants

Reaction Steps

40 ml of nitrobenzene and 12 ml of monochloroacetyl chloride (V) were added to 7.4 g of 1-methyl-8-hydroxycarbostyril (VI), and 20 g of aluminum chloride was added slowly to the mixture while cooling with ice-water followed by allowing the mixture to react at a temperature of 60° C. for 18 hours while stirring. The reaction mixture was then poured into 500 ml of ice-water to precipitate the product. The precipitate was filtered, washed with diethyl ether and recrystallized from a mixture of ethanol and dimethylformamide (1:1 by volume) to obtain 2.8 g of white amorphous 1-methyl-5-chloroacetyl-8-hydroxycarbostyril (IV) having a melting point of 287° to 289° C. (with decomposition). The product thus obtained was confirmed by elemental analysis and IR and NMR spectral analyses.

Provenance & Evidence