Sodium Chloride → 1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.2 g of 1,5-naphthyridin-2(1H)-one in 24 mL of N,N-dimethylformamide, 0.82 g of 60% sodium hydride was added at 60° C., and the mixture was stirred at the same temperature for 20 minutes, and then stirred at 55 to 80° C. for 30 minutes. Thereto was added 1.3 mL of 2-bromomethyl-1,3-dioxolan at 60° C., the temperature of the reaction mixture was increased to 100° C. over 4 hours, and to the reaction mixture, 2.3 g of potassium carbonate was added, and the mixture was stirred at the same temperature for 3 hours. After leaving overnight, 0.85 mL of 2-bromomethyl-1,3-dioxolan and 0.33 g of 60% sodium hydride were added thereto, and the mixture was stirred at 70 to 75° C. for 1 hour 30 minutes. The reaction mixture was cooled to room temperature, water, sodium chloride and chloroform were then added thereto, and the organic layer was separated. The aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=49:1 to obtain 1.1 g of 1-(1,3-dioxolan-2-ylmethyl)-1,5-naphthyridin-2(1H)-one as a light yellow solid.

Provenance & Evidence