Sodium Carbonate → HCID 135462828, compound

Participants

Reaction Conditions

Reaction Steps

To 6-methoxy-3-tetrazolyl-1,2-dihydroquinolin-2-one sodium salt (36.7 g, 138 mmol), sodium carbonate (14.7 g, 138 mmol), and tetra-n-butylammoniumbromide (22.3 g, 66.1 mmol), was added DMF (2 liters). (2-Quinolylmethoxy)benzyl chloride (58.7 g) was added to the resultant mixture, and the mixture was stirred for 15 hours at a bath temperature of 80° C. Subsequently, the solvent of the reaction mixture was removed under reduced pressure. To the obtained residue was added an 2N sodium hydroxide aqueous solution (1 liter). The organic phase was extracted from the solution with a mixture of chloroform-methanol (5:1). The organic phase was dried over sodium sulfate anhydrate, recrystallized from ethyl acetate, subjected to silica gel column chromatography (chloroform-methanol (5:1)), and concentrated under reduced pressure. The obtained residue was recrystallized from a chloroform-methanol-ether mixture, to thereby obtain crude 6-methoxy-3-{2-[3-(2-quinolylmethoxy)benzyl]tetrazolyl}quinolin-2-one as first-deposited crystals, and crude 6-methoxy-3-{1-[3-(2-quinolylmethoxy)benzyl]tetrazolyl}quinolin-2-one as second-deposited crystals.

Provenance & Evidence