Ammonium Acetate → HCID 15293173, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-phenylpyrano[3,4-b]pyridin-5-one (340 mg, 1.5 moles) in 10 ml DMF was added solid ammonium acetate (180 mg, 2.3 mmoles). The solution was heated to 80° C. under nitrogen for 18 hours, cooled and concentrated under vacuum. The solution was then flashed chromatographed eluting with ethyl acetate to give 245 mg (73% yield) of the desired 8-phenyl-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 260°-263° C.; 1H NMR (DMSO-d6, 300 MHz) δ7.38-7.65 (m, 7H), 8.64 (dd, 1H, J=8.1, 1.8 Hz), 8.98 (dd, 1H, J=4.5, 2.0 Hz), 11.83 (b, 1H); 13C NMR (75 MHz, DMSO-d6) δ 161.72, 153.98, 152.24, 135.55, 131.56, 129.93, 127.79, 126.77, 121. 62, 118.43; mass spectrum (EI), m/e 222.

Provenance & Evidence