Reaktion #417900

Reaktionsgleichung

3-chlorobenzoic acid

Water

dibenzo[f,h]quinoxaline

→

Dibenzo[f,h]quinoxaline-1-oxide

Ausbeute 51.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe organic layer was extracted with dichloromethane
2. 2
   WaschenThe obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   FiltrationThen, the resulting solution was filtered
5. 5
   workup.DISTILLATIONThe solvent of this solution was distilled off
6. 6
   SonstigeThe resulting residue was purified by silica gel column chromatography which
7. 7
   SonstigeBy recrystallization from dichloromethane
8. 8
   Sonstigethe object of the synthesis was obtained (as a white powder in a yield of 51%)
9. 9
   SonstigeThe synthesis scheme of Step 1

Vorschrift

First, to a solution in which 1.36 g of dibenzo[f,h]quinoxaline was dissolved in 20 mL of dichloromethane was added 2.04 g of 3-chlorobenzoic acid (abbreviation: MCPBA) in a nitrogen atmosphere, followed by stirring at room temperature for 1 week. Water was added to this mixture, and the organic layer was extracted with dichloromethane. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. Then, the resulting solution was filtered. The solvent of this solution was distilled off. The resulting residue was purified by silica gel column chromatography which uses a mixed solvent of dichloromethane and ethyl acetate as a developing layer. By recrystallization from dichloromethane, the object of the synthesis was obtained (as a white powder in a yield of 51%). The synthesis scheme of Step 1 is illustrated in the following (a″′-2-1).

Quelle