反应详情

2-[(Phenylmethyl)thio]pyridine-3-carboxaldehyde (6.01 g, 26.2 mmole, 1 equiv.), 1-(2-aminophenyl)-2-(methylsulfinyl)ethanone (5.17 g, 26.2 mmole, 1 equiv.), and piperidine (1.3 ml, 13.1 mmole, 0.5 equiv.) were combined in toluene (240 ml), and the mixture was heated to reflux under a Dean - Stark trap. After 3.5 hr, the reaction was concentrated to one half volume and cooled in the refrigerator overnight. Filtration of the mixture gave 2-[2-[(phenylmethyl)thio]-3-pyridinyl]-4(1H)-quinolinone (2.37 g, 26%) as a pale yellow solid: mp 219-226 (dec); TLC (50% EtOAc/CHCl3) Rf 0.19; 1H NMR (DMSO-d6) δ11.93 (br s, 1 H), 8.67 (dd, J=4.8, 1.8 Hz, 1 H), 8.10 (dd, J=8.1, 1.1 Hz, 1 H), 7.87 (dd, J=7.7, 1.8 Hz, 1 H), 7.60-7.72 (m, 1 H), 7.58 (d, J=8.0 Hz, 1 H), 7.17-7.45 (m, 7 H), 6.06 (br s, 1 H), 4.44 (s, 2 H); IR (KBr) 2100-3300 (br), 1633, 1595, 1573, 1549, 1534, 1502, 1474, 1440 cm-1 ; MS (NH3), m/e (%) 345.0 (100, (M+H)+), 255.1 (22.7), 253.1 (20.7). Anal. Calcd for C21H16N2OS: C, 73.23; H, 4.68; N, 8.13; S, 9.31. Found: C, 72.98; H, 4.56; N, 8.03; S, 9.20.

1. temperaturethe mixture was heated
2. temperatureto reflux under a Dean - Stark trap
3. concentrationthe reaction was concentrated to one half volume
4. temperaturecooled in the refrigerator overnight
5. filtrationFiltration of the mixture