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 11015Notes

Reaction equation

HRID 11015 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

HCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-821c8a69027f4a4db5de142cdbbeb36c
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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