Reaction #68004

Reaction equation

trifluoroacetic acid

1-(1,3-dioxolan-2-ylmethyl)-4-chloroquinolin-2(1H)-one

→

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

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe organic layer was washed sequentially with water
4. 4
   Dryingan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
5. 5
   Otherthe solvent was removed under reduced pressure

Procedure

Into 3 mL of a 90% aqueous trifluoroacetic acid solution, 156 mg of 1-(1,3-dioxolan-2-ylmethyl)-4-chloroquinolin-2(1H)-one was dissolved, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and the reaction mixture was alkalified with an aqueous saturated sodium hydrogen carbonate solution, and then extracted with ethyl acetate. The organic layer was washed sequentially with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 192 mg of a pale yellow oily substance, (4-chloro-2-oxoquinolin-1(2H)-yl)acetaldehyde.

Source