Reacción #417900

Ecuación de reacción

3-chlorobenzoic acid

Water

dibenzo[f,h]quinoxaline

→

Dibenzo[f,h]quinoxaline-1-oxide

Rendimiento 51.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente