Dimethylformamide → 7-(4-Chlorobutoxy)-1H-quinolin-2-one

Participants

Reaction Conditions

Reaction Steps

After 7-hydroxy-1H-quinolin-2-one (10 g) and DMF (50 ml) were heated to approximately 30° C., an aqueous potassium carbonate solution (potassium carbonate: 8.6 g, water: 10 ml) was added. After the mixture was stirred at 30 to 40° C. for about 15 minutes, 1-bromo-4-chlorobutane (14.3 ml) was added and stirred at approximately 40° C. for 5 hours. Water (100 ml) was added dropwise over a period of 30 minutes or more while the temperature was maintained at 30° C. or more. After the mixture was stirred at approximately 30° C. for 30 minutes, stirring was continued at 10° C. or less for 1 hour, after which the precipitated crystals were collected by filtration. After methanol (100 ml) was added to the precipitated crystals, the mixture was stirred under reflux to ensure dissolution. This solution was cooled and stirred at 30 to 40° C. for 30 minutes and then at 5° C. or less for about 1 hour, after which the precipitated crystals were collected by filtration. The crystals were dried at 60° C. to obtain 7-(4-chlorobutoxy)-1H-quinolin-2-one as white powder.

Provenance & Evidence