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

Temperature

0 °C

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.

1. temperaturewarmed to room temperature
2. stirringstirred overnight (14 h)
3. customThe reaction mixture was then quenched with ice
4. extractionextracted with ethyl acetate (2×100 mL)
5. washThe combined organic layers were washed with brine (1×100 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under reduced pressure

ORD record

ord-f01c9dc68ccc436fb98d77eefe2807c9

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2