Methanol → HCID 15411287, compound

Participants

Reaction Steps

3-(2-quinolinylmethoxy)benzyl chloride (3.49 g, 12.3 mmol) was added to a solution of 2.45 g (12.3 mmol) of 3-cyano-6-hydroxy-1,2-dihydroquinolin-2-one in 100 ml of DMF, followed by the further addition of 2.04 g (14.8 mmol) of K2CO3 and 396 mg (1.23 mmol) of tetra-n-butylammonium bromide. The resulting mixture was stirred under an argon gas stream at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, followed by the addition of CHCl3 --MeOH and water to extract the reaction product into the organic layer. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column. Subsequent to elution with CHCl3, recrystallization was conducted from a CHCl3 --MeOH mixed solvent, whereby 250 mg of the title compound were obtained as yellow powder (yield: 4.7%). Melting point: 145-147° C. (decomposed).

Provenance & Evidence