Sulfuric Acid → HCID 20253634, compound

Participants

Reaction Steps

To a mixture containing 16.7 g of 5-phenyl-1,6-naphthyridin-2(1H)-one and 250 ml of concentrated sulfuric acid was added portionwise 7.6 g of potassium nitrate with stirring, keeping the mixture in an ice bath. The addition was completed within 15 minutes and the temperature of the reaction mixture was kept below 10° C. during addition. The reaction mixture was then stirred in the ice bath for 40 minutes, allowed to warm up to room temperature and then stirred at room temperature for 5 and 1/2 hours. The reaction mixture was poured over ice and the resulting mixture was made basic using concentrated ammonium hydroxide solution. The mixture was made slightly acidic using glacial acetic acid and chilled. The separated solid was collected and dried. The solid was recrystallized from boiling dimethylformamide using decolorizing charcoal, the hot mixture filtered and the filtrate chilled. The separated solid was collected, washed with ethanol and dried in a vacuum oven at 90° C. to yield 12.2 g of 5-(3-nitrophenyl)-1,6-naphthyridin-2 (1H)-one, m.p. >300° C.

Provenance & Evidence