Pyridine → 2-(2-Oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)ethyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of 6-(2-hydroxyethoxy)-3,4-dihydroquinolin-2(1H)-one (0.15 g, 0.724 mmol) in DCM (2 mL) was added pyridine (0.117 mL, 1.448 mmol) and 4-methylbenzene-1-sulfonyl chloride (0.152 g, 0.796 mmol) and the reaction was stirred for 4 h. The reaction was diluted with EtOAc (25 mL), washed with 0.1 N HCl (10 mL), brine (10 mL), and sat. NaHCO3 solution (10 mL). The organic layer was dried over sodium sulfate, evaporated to dryness, and purified by flash chromatography on silica gel (4 g, 50% EtOAC in hexanes) to yield 2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)ethyl 4-methylbenzenesulfonate (0.07 g, 27%).

Provenance & Evidence