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

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (80 mg, 3.32 mmol) was taken in THF (1 mL) and cooled to 0° C. To the suspension, 4-(4-chloro-2-fluorophenyl)-N-methylnicotinamide (440 mg, 1.66 mmol) in THF (1 mL) was added dropwise and the temperature was maintained at 0° C. for 30 min. The reaction mixture was then warmed to room temperature and stirred for 2 h. The reaction mixture was quenched with ice and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (1×5 mL) dried (Na2SO4) and concentrated under reduced pressure to afford 8-chloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (440 mg, 1.798 mmol) as a light brown oil. LC/MS (ESI) m/e 245.1 [(M+H)+, calcd for C13H10ClN2O 245.1]; LC/MS retention time (method C): tR=1.79 min.

Provenance & Evidence