Réaction #5229

Équation de réaction

2-Phenyl-pyrrolo[3,4-c]quinolin-3(1H)-one

m-chloroperbenzoic acid

→

2-Phenyl-pyrrolo[3,4-c]quinoline-3(1H),4(5H)-dione

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   Lavagewashed with sodium carbonate solution
2. 2
   SéchageThe organic layer was dried over magnesium sulfate
3. 3
   Autrethe solvent was removed in vacuo
4. 4
   AutreThe reaction was quenched with methanol
5. 5
   ConcentrationThe reaction mixture was concentrated in vacuo
6. 6
   Extractionthe resulting aqueous solution was extracted with ethyl acetate
7. 7
   Séchagethe organic layer was dried over magnesium sulfate
8. 8
   Autrethe solvent was removed in vacuo
9. 9
   AutreThe residue was triturated with ether

Mode opératoire

A mixture of 2-Phenyl-pyrrolo[3,4-c]quinolin-3(1H)-one (60 mg), and m-chloroperbenzoic acid (105 mg) in 3 mL of methylene chloride was kept at room temperature for 24 h. The mixture was diluted with methylene chloride and washed with sodium carbonate solution. The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was heated at 50° C. for 3 h with 1 mL of acetic anhydride. The reaction was quenched with methanol and made basic with ammonium hydroxide. The reaction mixture was concentrated in vacuo, and the resulting aqueous solution was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was triturated with ether to afford 2-Phenyl-pyrrolo[3,4-c]quinoline-3(1H),4(5H)-dione (Compound 16) as a white solid.

Source