反应详情

To a solution of boron trichloride (55 g) in 1,2 dichloroethane at 0° was added dropwise a solution of o-toluidine (45.7 g, 0.426 mol) in 1,2 dichloroethane (50 ml) maintaining the temperature below 5°. On completion of the addition 4-chlorobutyronitrile (41.4 g, 0.426 mol) and aluminium chloride (53.34 g, 0.426 mol) were added successively. The reaction mixture was allowed to warm up to room temperature and stirred for 1.5 hours, then heated under reflux for 20 hours. The reaction mixture was then cooled to room temperature poured onto ice (500 g) and 2N hydrochloric acid (200 ml). The mixture was then heated under reflux for 0.5 hour. The organic layer was separated and the aqueous layer was extracted with chloroform (3×100 ml). The organic extracts were combined, washed with water, dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil was dissolved in diethyl ether and HCl gas bubbled through. The resulting solid was collected by filtration and dried (57 g). Recrystallization from ethanol/diethyl ether gave the title compound, m.p. 148-150°.

1. temperaturemaintaining the temperature below 5°
2. additionwere added successively
3. temperatureheated
4. temperatureunder reflux for 20 hours
5. temperatureThe reaction mixture was then cooled to room temperature
6. temperatureThe mixture was then heated
7. temperatureunder reflux for 0.5 hour
8. customThe organic layer was separated
9. extractionthe aqueous layer was extracted with chloroform (3×100 ml)
10. washwashed with water
11. dry with materialdried over magnesium sulphate
12. filtrationfiltered
13. customevaporated under reduced pressure
14. customto give an oil
15. customHCl gas bubbled through
16. filtrationThe resulting solid was collected by filtration
17. customdried (57 g)
18. customRecrystallization from ethanol/diethyl ether