2-Chloroquinoline → HCID 22241416, compound

Participants

Reaction Steps

To a suspension of 60% NaH (44 mg, 1.1 mmol) in DMSO (2 mL) is added dropwise a solution of [3-(2-methoxy-ethoxymethoxy)-phenyl]-methanol (212 mg, 1.0 mmol, example 72) in DMSO (1 mL). Let stir 20 min. then added 2-chloroquinoline (180 mg, 1.1 mmol) and heated to 100° C. for 1 hr. Cooled reaction mixture to room temp. and diluted with EtOAc. The organic layer is washed with sat. NH4Cl soln., brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 25% ethyl acetate in hexanes) to give the title compound as a colorless oil. MS (ESI) 340 (M+H)+.

Provenance & Evidence