Reacción #68178

Ecuación de reacción

dichloromethane

oxalyl chloride

dimethylsulfoxide

dichloromethane

4-chloro-1-(2-hydroxyethyl)-7-trifluoromethylquinolin-2(1H)-one

→

(4-chloro-7-trifluoromethyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

Disolventes

water

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise under nitrogen atmosphere at −60° C.
2. 2
   workup.ADDITIONwas added dropwise at the same temperature
3. 3
   workup.STIRRINGstirred for 10 min
4. 4
   workup.STIRRINGthe mixture was stirred for 1 hour
5. 5
   OtroThe organic layer was separated
6. 6
   Extracciónthe aqueous layer was extracted with chloroform
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Otrothe solvent was removed under reduced pressure

Procedimiento

To 2 mL of a dichloromethane solution containing 10 μL of oxalyl chloride, 20 μL of dimethylsulfoxide was added dropwise under nitrogen atmosphere at −60° C., and stirred for 10 min. 3 mL of a dichloromethane solution containing 31 mg of 4-chloro-1-(2-hydroxyethyl)-7-trifluoromethylquinolin-2(1H)-one was added dropwise at the same temperature, and stirred for 10 min. 60 μL of triethylamine was added at the same temperature, the mixture was stirred for 1 hour while slowly raising the reaction mixture to room temperature, and water was added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give (4-chloro-7-trifluoromethyl-2-oxoquinolin-1(2H)-yl)acetaldehyde as a brown oil.

Fuente