反应详情

To a slurry of 4-oxo-1,4,5,6,7,8-hexahydrocinnoline-3-carboxylic acid ethyl ester (1 g), lithium chloride (0.19 g) and pyridine (0.36 ml) in dichloromethane (30 ml) was added p-toluenesulphonyl chloride (0.85 g). The reaction mixture was heated at reflux for 20 h. The solid was collected by filtration, and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography using a gradient elution: CH2Cl2 (500 ml), CH2Cl2/MeOH 99:1 (500 ml), CH2Cl2/MeOH 98:2 (1 liter). The appropriate fractions were combined and evaporated under reduced pressure to give a solid (0.65 g, 61%). δH (360 MHz; CDCl3) 1.44 (3H, t, J=7 Hz, CH3), 1.89 (4H, m, CH2), 2.85 (2H, t, J=5.7 Hz, CH2), 2.62 (2H, t, J=5.7 Hz, CH2), 4.51 (2H, t, J=7 Hz, CH2), m/z (ESP+) 241/243 (MH+).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 20 h
3. filtrationThe solid was collected by filtration
4. customthe filtrate was evaporated under reduced pressure
5. customThe residue was purified by flash chromatography
6. washa gradient elution
7. customevaporated under reduced pressure