反应详情

温度

-5 °C

1-(2-(Dimethylamino)ethyl)-8-fluoro-3,4-dihydroquinolin-2(1H)-one (2.86 g, 12.11 mmol) was weighed into a round bottom flask equipped a stir bar. To this was added concentrated sulfuric acid (30 mL) and the flask was cooled to −5° C. in an ice/salt bath. To this stirring solution was added nitric acid (90%, 615.5 μL, 13.2 mmol) and the resulting mixture was stirred for 30 min. The reaction mixture was then quenched with ice and NaOH(aq). The product was extracted with CH2Cl2 (3×). The combined organics were dried, filtered and concentrated then chromatographed on silica using 0-10% (2M NH3 in MeOH) in dichloromethane, giving the desired product. Yield: 1.1 g, 32%, product still contains some impurities). 1H NMR (CDCl3) δ 2.20 (s, 6H), 2.48 (t, 2H, J=7.0 Hz), 2.67 (t, 2H, J=7.0 Hz), 2.98 (t, 2H, J=7.0 Hz), 4.16 (t, 2H, J=7.0 Hz), 7.89 (m, 2H). ESI-MS: 282 (MH+, 100), 237 (50), 192 (27).

1. customequipped a stir bar
2. customThe reaction mixture was then quenched with ice and NaOH(aq)
3. extractionThe product was extracted with CH2Cl2 (3×)
4. customThe combined organics were dried
5. filtrationfiltered
6. concentrationconcentrated
7. customthen chromatographed on silica using 0-10% (2M NH3 in MeOH) in dichloromethane