Sodium hydride → 8-chlorobenzo[c][2,7]naphthyridin-5(6H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-chloro-2-fluorophenyl)nicotinamide (0.9 g, 3.59 mmol) in THF (20 mL) at 0° C. was added sodium hydride (0.258 g, 10.77 mmol) and the reaction mixture was stirred at 0° C. for 1 h and then warmed to room temperature and stirred overnight (14 h). The reaction mixture was then quenched with ice and extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (1×100 mL), dried (Na2SO4) and concentrated under reduced pressure to afford crude 8-chlorobenzo[c][2,7]naphthyridin-5(6H)-one (0.80 g, 3.47 mmol, 97% yield). LC/MS (ESI) m/e 231.2 [(M+H)+, calcd for C12H8ClN2O 231]; LC/MS retention time (method D): tR=0.61 min.

Provenance & Evidence