Hydrochloric Acid → 5-Fluoro-3,4-dihydroquinolin-2(1H)-one
반응식
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:3]=1[CH2:4][CH:5](C(OCC)=O)[C:6](OCC)=[O:7].Cl>C(O)(=O)C>[F:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:2]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:7])[NH:1]2참가 물질
4
반응 조건
- 온도
- 90 °C
실험 절차
To a stirred solution of diethyl 2-(2-amino-6-fluorobenzyl)malonate (146-3; 2.0 g, 0.00706 mol)) in acetic acid (20 mL) was added hydrochloric acid (20 mL). The reaction mixture was heated at 90° C. for 1 h. The reaction mixture was cooled to room temperature and then poured into ice cold water. It was extracted with ethyl acetate (3×40 mL). The combined organic layer was washed with 10% aqueous sodium hydroxide solution, saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the title compound. 1H NMR (400 MHz, DMSO) δ 10.219 (s, 1H), 7.164-7.108 (q, J=7.6 Hz, 1H), 6.769-6.725 (t, J=8.4 Hz, 1H), 6.684-6.664 (d, J=8.0 Hz, 1H), 2.871-2.832 (t, J=7.6 Hz, 2H), 2.472-2.434 (t, J=8.0 Hz, 2H). MS (M+1): 166.1.