Reaktion #342506

Reaktionsgleichung

1,2-dimethoxy-4,5-dinitrobenzene

ethyl oxoacetate

→

product

Ausbeute 38.8%

6,7-Dimethoxyquinoxalin-2(1H)-one

Ausbeute 38.8%

Lösungsmittel

ethanol acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through a pad of celite
2. 2
   workup.ADDITIONThe filtrate containing the crude diamine
3. 3
   FiltrationThe resulting precipitate was collected by filtration
4. 4
   workup.ADDITIONThis material was suspended in a mixture of methanol/dichloromethane and solvent
5. 5
   Sonstigewas removed under reduced pressure
6. 6
   Sonstigeto remove traces of acetic acid

Vorschrift

A mixture of 1,2-dimethoxy-4,5-dinitrobenzene (5.7 g, 25.0 mmol) in ethanol/acetic acid (140 mL, 1:1) was hydrogenated over palladium on carbon (10%, 1 g) at normal pressure and room temperature for 3 hours, then filtered through a pad of celite. The filtrate containing the crude diamine was treated with ethyl oxoacetate (50 wt % in toluene, 10 mL, 50 mmol) and the reaction was stirred at room temperature overnight. The resulting precipitate was collected by filtration. This material was suspended in a mixture of methanol/dichloromethane and solvent was removed under reduced pressure to remove traces of acetic acid to give 2.0 g (38%) of product as a solid.

Quelle