Reaktion #52688

Reaktionsgleichung

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

Ausbeute 13.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle