Reaktion #52656

Reaktionsgleichung

hydrochloric acid

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

5-chloro-2-oxindole

pyrrolidine

→

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

Ausbeute 10.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe solid which remained were filtered
2. 2
   Waschenwashed with more water (50 ml)
3. 3
   workup.DISSOLUTIONThe solid was then dissolved in ethyl acetate (200 ml)
4. 4
   Trocknenthe solution dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe solid which remained 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, 1.26 mmol), 5-chloro-2-oxindole (0.21 g, 1.26 mmol) and pyrrolidine (0.5 ml, 6.3 mmol) in ethanol (2 ml) was held in sealed tube at 100° C. for 12 hours. The mixture was then poured into 1N hydrochloric acid (100 ml) and the solid which remained were filtered and washed with more water (50 ml). The solid was then dissolved in ethyl acetate (200 ml), the solution dried over magnesium sulfate, filtered and then concentrated. The solid which remained was chromatographed (silica, 4/4/1 dichloromethane/hexanes/methanol) to give 60 mg (10%) of 5-chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one as a brownish-orange solid.

Quelle