2-Chloroquinoline → HCID 22241341, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[(2-methoxyethoxy)-methoxy]-benzylamine (422 mg, 2 mmol, example 9) in DMSO (4 mL) is added 2-chloroquinoline (328 mg, 2 mmol). The resulting solution is warmed to 140° C. and stirred at this temperature for 3 h. The resulting mixture is cooled, diluted with water, then extracted with ethyl acetate. The organic extract is washed with brine, dried over MgSO4 and concentrated. The residue is taken up in methanol (10 mL) then p-toluene sulphonic acid monohydrate (190 mg, 1 mmol) is added. This mixture is warmed to 60° C. and stirred at this temperature for 2 h. The reaction mixture is then cooled, concentrated under reduced pressure and the residue purified by flash chromatography (silica, 30% ethyl acetate in dichloromethane) to give the title compound. MS (ESI) 251 (M+H)+.

Provenance & Evidence