反应详情

In 300 ml of toluene and 200 ml of 30% potassium hydroxide were added 8.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 1.92 g of tetrabutylammonium hydrogn sulfate catalyst. The mechanically stirred biphasic solution was heated to reflux and 9.4 ml of 4-fluorobenzyl bromide in 50 ml of toluene was added dropwise. Reflux was continued for a total of 2 hours. The reaction was poured onto ice and the toluene layer was separated. The aqueous phase was extracted with ethyl acetate. The organics were combined, washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered and evaporated to a solid. The solid was recrystallized from 1:1 ethyl acetate/hexane to yield 5.89 g of product, mp 158°-159° C.

1. temperatureThe mechanically stirred biphasic solution was heated
2. temperatureto reflux
3. temperatureReflux
4. customwas continued for a total of 2 hours
5. additionThe reaction was poured onto ice
6. customthe toluene layer was separated
7. extractionThe aqueous phase was extracted with ethyl acetate
8. washwashed with saturated NaCl solution
9. dry with materialdried over anhydrous magnesium sulfate
10. filtrationfiltered
11. customevaporated to a solid
12. customThe solid was recrystallized from 1:1 ethyl acetate/hexane