Reaction #5229

Reaction equation

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

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Washwashed with sodium carbonate solution
2. 2
   DryingThe organic layer was dried over magnesium sulfate
3. 3
   Otherthe solvent was removed in vacuo
4. 4
   OtherThe 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
   Dryingthe organic layer was dried over magnesium sulfate
8. 8
   Otherthe solvent was removed in vacuo
9. 9
   OtherThe residue was triturated with ether

Procedure

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