25% | With 6-hydroxyquinoline; potassium carbonate;copper(l) iodide; In N,N-dimethyl-formamide; at 130℃; for 18h; | Synthesis of Lambda/-benzyl-2-(2-oxo-4-phenylpyridin-1 (2H)-yl)isonicotinamide <n="130"/>A degassed mixture of Lambda/-benzyl-2-chloroisonicotinamide (0.25 g, 1.01 mmol), 4- phenylpyridin-2(1 H)-one (0.17 g, 0.91 mmol), potassium carbonate (0.20 g, 1.44 mmol), 8-hydroxyquiniline (0.02 g, 0.14 mmol) and copper(l) iodide (0.03 g, 0.14 mmol) in N, N- dimethylformamide (3.0 ml.) was heated at 130 C for 18 hours. The resulting solution was cooled to ambient temperature, quenched with ammonium hydroxide solution (10 ml.) and extracted with ethyl acetate (2 x 25 ml_). The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to give Lambda/-benzyl-2-(2-oxo-4-phenylpyridin-1 (2H)- yl)isonicotinamide as a colorless solid (0.10 g, 25%): mp 162-163 0C; 1H NMR (300 MHz, DMSO-cfe) delta 9.43 (t, J = 5.1 Hz, 1 H), 8.73 (d, J = 5.1 Hz, 1 H), 8.24, (s, 1 H), 7.99 (d, J = 7.3 Hz, 1 H), 7.89 (d, J = 5.1 Hz, 1 H), 7.79-7.76 (m, 2H), 7.54-7.45 (m, 3H), 7.36-7.18 (m, 5H), 6,82 (s, 1 H), 6.76 (d, J = 7.3 Hz, 1 H), 4.48 (d, J = 5.7 Hz, 2H); 13C NMR (75 MHz, DMSO-CZ6) delta 164.2, 161.6, 152.7, 152.0, 150.2, 143.6, 139.4, 137.4, 136.6, 130.5, 129.6, 128.8, 127.9, 127.4, 127.3, 121.6, 119.9, 116.8, 105.6, 43.3; MS (ES+) m/z 382.6 (M +1 ). |