反应详情

To pyridine (2.1 ml, 26 mmol) in EtOH (60 ml) was added 2-bromo-1-(2-chlorophenyl)ethanone (6.1 g, 26 mmol) in EtOH (40 ml) dropwise over 10 min. The resulting mixture was heated at 60˜70° C. for 1 hour and cooled to room temperature. To the mixture were added pyridine (1.25 ml), 2-amino-3-chlorobenzaldehyde (3.72 g, 24.0 mmol) and DMAP (0.05 g, cat.). The mixture was heated at reflux for 48 hrs. The reaction mixture was cooled to room temperature and pyrrolidine (4.60 ml, 55.0 mmol) was added. After heating at reflux overnight, the resulting mixture was concentrated. The residue was partitioned between saturated aqueous NaHCO3 and CH2Cl2. The combined organic layers were dried, concentrated. Flash chromatography of the residue over silica gel, using 3:7 EtOAc-hexane, gave 8-chloro-2-(2-chlorophenyl)-quinolin-3-amine, 1H-NMR (DMSO-d6) δ 7.67 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.50-7.57 (m, 3H), 7.46 (d, J=8.0 Hz, 1H), 7.42 (s, 1H), 7.39 (t, J=8.0 Hz, 1H), 5.32 (br, 2H). Mass Spectrum (ESI) m/e=289.0 (M+1).

1. temperatureThe resulting mixture was heated at 60˜70° C. for 1 hour
2. temperatureThe mixture was heated
3. temperatureat reflux for 48 hrs
4. temperatureThe reaction mixture was cooled to room temperature
5. temperatureAfter heating
6. temperatureat reflux overnight
7. concentrationthe resulting mixture was concentrated
8. customThe residue was partitioned between saturated aqueous NaHCO3 and CH2Cl2
9. customThe combined organic layers were dried
10. concentrationconcentrated