反应详情

4-Chloro-3-nitroquinoline (J. Med. Chem. 1974, 17, 245) (2.08 g, 0.01 mol) and 2-methylaniline (2.14 g, 0.02 mol) were dissolved in THF (50 ml) and the mixture stirred at reflux for 16 hours, during which time a pale yellow solid was deposited. After cooling, the solvent was evaporated and the residue dissolved in 2M HCl (80 ml). The acidic solution was extracted with CHCl3 (×3) and the chloroform solution washed with aqueous NaHCO3 and water. Drying and evaporation of the chloroform gave an orange-yellow solid which was crystallised from absolute ethanol to give the title compound (1.2 g, 43%) as orange needles, m.p. 137°-138°.

1. temperatureat reflux for 16 hours, during which time a pale yellow solid
2. temperatureAfter cooling
3. customthe solvent was evaporated
4. dissolutionthe residue dissolved in 2M HCl (80 ml)
5. extractionThe acidic solution was extracted with CHCl3 (×3)
6. washthe chloroform solution washed with aqueous NaHCO3 and water
7. customDrying
8. customevaporation of the chloroform
9. customgave an orange-yellow solid which
10. customwas crystallised from absolute ethanol