1-Bromo-2-Chloroethane → 1-(Quinolin-6-yl)cyclopropanecarbonitrile

Participants

Reaction Conditions

Reaction Steps

60 mL of 50% aqueous NaOH was added to a mixture of 1-bromo-2-chloroethane (22.0 mL, 0.265 mol), quinolin-6-ylacetonitrile (16.0 g, 0.0666 mol), and benzyltriethylammonium chloride (0.99 g, 0.0043 mol) at 50° C. The mixture was stirred at 50° C. for 3 h. After cooling to RT, the reaction mixture was poured into 100 ml of water, and extracted with DCM (3×100 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered through a pad of silica gel and washed with ethyl acetate in DCM (20%). The filtrate was concentrated to give the crude product 1-quinolin-6-ylcyclopropanecarbonitrile (12.4 g, 96%) which was directly used in the next step without further purification.

Provenance & Evidence