反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
1-(2-(Dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (1.16 g, 4.40 mmol) was dissolved in dichloromethane (20 mL) in a round bottom flask at room temperature. The solution was cooled to 0° C. and phenyl chloroformate (0.829 mL, 6.61 mmol) was added slowly to avoid an excessive exotherm. The reaction mixture was then warmed to room temperature and stirred overnight. The reaction mixture was then diluted with dichloromethane and quenched with dilute NaOH (˜0.5 M). The aqueous phase was extracted with dichloromethane (3×) and the combined organics were dried over sodium sulfate, filtered and concentrated. The resulting residue was then chromatographed in 50-100% ethyl acetate in hexanes. Yield: 1.29 g, 78%. 1H NMR (CDCl3) δ 8.13 (dd, 1H, J=9.0, 2.7 Hz), 8.05 (t, 1H, J=3.3 Hz), 7.41 (m, 3H); 7.23 (m, 1H); 7.06 (m, 2H), 4.23 (m, 2H), 3.70 and 3.58 (2t, 2H, J=7.2 Hz), 3.19 and 3.09 (2s, 3H), 3.00 (t, 2H, J=7.4 Hz), 2.72 (t, 2H, J=7.4 Hz); ESI-MS (m/z, %): 392 (MNa+, 100), 370 (MH+, 28).
WORKUP
后处理
- temperatureThe reaction mixture was then warmed to room temperature
- customquenched with dilute NaOH (˜0.5 M)
- extractionThe aqueous phase was extracted with dichloromethane (3×)
- dry with materialthe combined organics were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe resulting residue was then chromatographed in 50-100% ethyl acetate in hexanes