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

Participants

Reaction Steps

30 ml of nitrobenzene and 70 ml of chloroacetyl chloride (V) were added to 40 g of 1-methyl-8-methoxycarbostyril (VI), and 130 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 4 hours while stirring. The reaction mixture was then poured into one liter of ice-water to precipitate the product. The precipitate was filtered, washed with diethyl ether and recrystallized from a mixture of chloroform and ethanol (2:5 by volume) to obtain 32 g of white amorphous 1-methyl-5-chloroacetyl-8-methoxycarbostyril (IV) having a melting point of 204° to 205.5° C. The product thus obtained was confirmed by elemental analysis and IR and NMR spectral analyses.

Provenance & Evidence