Reaktion #11111

Reaktionsgleichung

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

Ausbeute 89.5%

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added in one portion
2. 2
   Sonstigeto dry
3. 3
   Sonstigefreshly-prepared pyridine hydrochloride
4. 4
   Sonstigemelt at 200° C. under a CaCl2 drying
5. 5
   Extraktionthe mixture was extracted with EtOAc
6. 6
   TrocknenThe EtOAc extracts were dried
7. 7
   Sonstigethe drying agent was removed
8. 8
   Einengenthe solution was concentrated to dryness
9. 9
   Sonstigeto give a solid which
10. 10
    Sonstigewas chromatographed on silica
11. 11
    WaschenElution with EtOAc

Vorschrift

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.

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