반응 #52688

반응 방정식

hydrochloric acid

3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

5-bromo-2-oxindole

pyrrolidine

→

5-bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one

수율 13.0%

용매

ethanol

반응 조건

후처리

1. 1
   기타the solids removed by filtration
2. 2
   세척washed with more water (50 ml)
3. 3
   workup.DISSOLUTIONThe solids were then dissolved in ethyl acetate (200 ml)
4. 4
   세척the solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml)
5. 5
   건조dried with magnesium sulfate
6. 6
   농축concentrated
7. 7
   기타The crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol)

실험 절차

A mixture of 3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde (0.4 g), 5-bromo-2-oxindole (0.27 g) and pyrrolidine (0.5 ml) in ethanol (2 ml) was held in a sealed tube at 100° C. for 12 hours. The mixture was then added to 1N hydrochloric acid (100 ml) and the solids removed by filtration and washed with more water (50 ml). The solids were then dissolved in ethyl acetate (200 ml), the solution washed with 1N hydrochloric acid (75 ml) and brine (75 ml), dried with magnesium sulfate and concentrated. The crude solid was chromatographed (silica, 4:4:1 dichloromethane:hexanes:methanol) to give 80 mg (13%) of 5-bromo-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one as a reddish-brown solid.

출처