Dimethylformamide → 6-Benzyl-8-phenyl-1,6-naphthyridin-5-one

Participants

Reaction Steps

To a solution of 8-phenylpyrano [3,4-b]pyridin-5-one (100 mg, 0.45 mmoles) in 5 ml DMF was added benzylamine (0,006 ml, 0.54 mmoles) under nitrogen. The reaction mixture was heated overnight to 80° C., cooled and concentrated under vacuum to give 253 mg of crude product. The crude product was chromatographed eluting with 1:1 EtOAc/Hexanes to give 72 mg (51% yield) of the desired 6-benzyl-8-phenyl-1,6-naphthyridin-5-one as a white solid. Characteristic analytical data are as follows: mp 166°-167° C.; 1H NMR (CDCl3, 300 MHz) δ5.31 (s, 2H), 7.28-7.58 (m, 12H) 8.82 (dd, 1H, J=8.2, 1.8 Hz) 8.98 (dd, 1H, J=4.6, 2.0 Hz); 13C NMR (75 MHz, CDCl3) δ161.88, 154.10, 151.84, 137.00, 136.29, 135.06, 134.24, 130.02, 129.02, 128.40, 128.19,128.12, 127.77, 122.06, 121.09,120.99, 52.00; mass spectrum (CI) , m/e 312; exact mass calcd. for C21H16N2O 312.1263, found 312.1259.

Provenance & Evidence