Triethylamine → 3-Phenoxy-N-quinolin-6-yl-benzamide

Participants

Reaction Steps

To a solution of 6-aminoquinoline (250 mg, 1.04 mmol) in N,N-dimethylformamide (15 mL) were added 3-phenoxybenzoic acid (371 mg, 1.73 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (722 mg, 1.90 mmol) and triethylamine (603 μl, 4.33 mmol), and the solution was stirred for 2 days at room temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate, the organic layer was washed with water, an aqueous solution of saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and then, concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate), and the title compound (328 mg, 0.964 mmol, 93%) was obtained.

Provenance & Evidence