4-Iodo-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione → 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11015
[I:1][C:2]1[C:14]2[C:15](=[O:19])[NH:16][C:17](=[O:18])[C:13]=2[C:12]2[C:11]3[CH:10]=[C:9]([O:20]C)[CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH:3]=1>O>[OH:20][C:9]1[CH:8]=[CH:7][C:6]2[NH:5][C:4]3[CH:3]=[C:2]([I:1])[C:14]4[C:15](=[O:19])[NH:16][C:17](=[O:18])[C:13]=4[C:12]=3[C:11]=2[CH:10]=1

Komponenten

3

Edukt 1

HCID 118435494-Iodo-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Produkt 1

HCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Powdered 4-Iodo-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (0.50 g, 1.27 mmol) prepared as in example 6 was added in one portion to dry, freshly-prepared pyridine hydrochloride melt at 200° C. under a CaCl2 drying tube and the mixture was stirred at this temperature for 15 min. Water was added and the mixture was extracted with EtOAc. The EtOAc extracts were dried, the drying agent was removed and the solution was concentrated to dryness to give a solid which was chromatographed on silica. Elution with EtOAc gave 9-Hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (8) (0.43 g, 89%) as an orange powder; mp>350° C. 1H NMR δ [(CD3)2SO] 11.76 (br s, 1H), 11.24 (br s, 1H), 9.29 (br s, 1H), 8.27 (d, J=2.4 Hz, 1H), 8.13 (s, 1H), 7.44 (d, J=8.7 Hz, 1H), 7.08 (dd, J=8.7, 2.4 Hz, 1H). Found: C, 44.90; H, 1.79; N, 7.14. C14H71N2O3 requires C, 44.47; H, 1.87; N, 7.40.

Aufarbeitung

  1. additionwas added in one portion
  2. customto dry
  3. customfreshly-prepared pyridine hydrochloride
  4. custommelt at 200° C. under a CaCl2 drying
  5. extractionthe mixture was extracted with EtOAc
  6. dry with materialThe EtOAc extracts were dried
  7. customthe drying agent was removed
  8. concentrationthe solution was concentrated to dryness
  9. customto give a solid which
  10. customwas chromatographed on silica
  11. washElution with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-821c8a69027f4a4db5de142cdbbeb36c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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