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

HRID 5133Notes

Reaction equation

HRID 5133 reaction equation
[C:1]1([N:7]2[CH2:19][C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]=[CH:10][C:9]=3[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[C:1]1([N:7]2[CH2:19][C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:11][C:10](=[O:29])[C:9]=3[C:8]2=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57023940HCID 57023940, compound

Product 1

HCID 138117802-Phenyl-pyrrolo[3,4-c]quinoline-3(1H),4(5H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

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.

Workup

  1. washwashed with sodium carbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe reaction was quenched with methanol
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. extractionthe resulting aqueous solution was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-85ced26261244ccdada566c55d307030
Source dataset
uspto-grants-1993_09
Patent number
US05243049

Reaction notes

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