Réaction #68013

Équation de réaction

1-(1,3-dioxolan-2-ylmethyl)-8-methylquinolin-2(1H)-one

trifluoroacetic acid

→

(8-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

Conditions de réaction

Traitement

1. 1
   workup.WAITat room temperature for 5 days
2. 2
   AutreThe solvent was removed under reduced pressure
3. 3
   workup.ADDITIONthe reaction mixture was added with ethyl acetate
4. 4
   AutreThe organic layer was separated
5. 5
   Extractionthe aqueous layer was extracted with ethyl acetate
6. 6
   Lavagethe resultant solution was washed with an aqueous saturated sodium chloride solution
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   Autrethe solvent was removed under reduced pressure

Mode opératoire

To 0.17 g of 1-(1,3-dioxolan-2-ylmethyl)-8-methylquinolin-2(1H)-one, 2 mL of a 90% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 4 days, at 40° C. for 3 days, and at room temperature for 5 days. The solvent was removed under reduced pressure, and the reaction mixture was added with ethyl acetate and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.14 g of a brown oily substance, (8-methyl-2-oxoquinolin-1(2H)-yl)acetaldehyde.

Source