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

HRID 1451291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451291
[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

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 57023940HCID 57023940, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1d6ca19c2d34480a8b08a5ba2eeccaa4
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604235

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