反应详情

4-Chloro-3-(2-chloroethyl)cinnoline (1.52 g, 0.0067 mol) and o-toluidine (1.43 g, 0.0134 mol) in 1,4 dioxan (20 ml) were heated under reflux for 20 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between chloroform and dilute sodium bicarbonate solution. The aqueous layer was extracted with chloroform (6×50 ml). The chloroform extracts were combined, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give a brown oil. The oil was purified by chromatography using chloroform (1 litre), chloroform/methanol (20:I) as eluant. The fractions containing the product were combined and evaporated under reduced pressure to give an oil. On trituration with diethyl ether a solid was obtained. The solid was collected by filtration and dried, 0.76 g. Recrystallization from ethyl acetate gave the title compound, 0.48 g, m.p. 140-142°.

1. temperatureunder reflux for 20 hours
2. customThe solvent was evaporated under reduced pressure
3. customthe residue was partitioned between chloroform and dilute sodium bicarbonate solution
4. extractionThe aqueous layer was extracted with chloroform (6×50 ml)
5. dry with materialdried over magnesium sulphate
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customto give a brown oil
9. customThe oil was purified by chromatography
10. additionThe fractions containing the product
11. customevaporated under reduced pressure
12. customto give an oil
13. filtrationThe solid was collected by filtration
14. customdried
15. customRecrystallization from ethyl acetate