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 11015ノート

反応式

HRID 11015 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-821c8a69027f4a4db5de142cdbbeb36c
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

反応ノート

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