反应详情

4-Chloro-5,6,7,8-tetrahydrocinnoline-3-carboxylic acid ethyl ester (0.5 g), 4-fluorophenylhydrazine hydrochloride (0.34 g) and H{umlaut over (u)}inig's base (0.73 ml) in xylene under nitrogen were heated under reflux for 2 h. The solid was collected by filtration, washed with diethyl ether, water and diethyl ether. The residue was recrystallised from ethanol to give the title compound (136 mg, 13%). δH (360 MHz; DMSO-d6) 1.83 (4H, m, CH2), 2.67 (2H, t, J=5.3 Hz, CH2), 2.72 (2H, t, J=5.3 Hz, CH2), 3.78 (3H, s, OCH3), 7.02 (2H, d, J=9 Hz, ArH), 8.06 (2H, d, J=9 Hz, ArH), m/z (ESP+) 285 (MH+). C15H13FN4O requires C, 63.37; H, 4.61; N, 19.71; found C, 62.96; H, 4.36; N, 19.48%.

1. temperatureunder reflux for 2 h
2. filtrationThe solid was collected by filtration
3. washwashed with diethyl ether, water and diethyl ether
4. customThe residue was recrystallised from ethanol