HRID1922411

反应详情

EQUATION

反应方程式

HRID 1922411 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

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

  1. temperatureThe reaction mixture was then warmed to room temperature
  2. customquenched with dilute NaOH (˜0.5 M)
  3. extractionThe aqueous phase was extracted with dichloromethane (3×)
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was then chromatographed in 50-100% ethyl acetate in hexanes