Hydrogen Peroxide → HCID 59375146, Verbindung

HRID 661943Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661943
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16](C=O)=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1.OO.S(=O)(=O)(O)[OH:29].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([OH:29])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 784Hydrogen Peroxide2×HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 86642953HCID 86642953, Verbindung

Produkt 1

HCID 59375146HCID 59375146, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Step 2 A solution of crude 4-(2-fluorophenyl)-7-formyl-9H-carbazole-1-carboxamide (25.2 mg, 0.076 mmol) in methanol (2 mL) at 0° C. was treated with 30% aqueous hydrogen peroxide (0.039 mL, 0.379 mmol) and sulfuric acid (0.020 mL, 0.379 mmol). After 1.5 h, additional hydrogen peroxide (0.100 mL) and sulfuric acid (0.050 mL) were added and the mixture was stirred at rt overnight. After 16 h, 1 M aqueous sodium hydroxide (2 mL) was added and the mixture was stirred for 1 h. The pH was adjusted to ca. 4 and the organic solvent was removed under vacuum. The aqueous residue was diluted with water and the precipitate was collected by filtration, washed with water and dried. The residue was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide as tan solid after lypholization (5.1 mg, 21%). 1H NMR (400 MHz, methanol-d4) δ 7.81 (1H, d, J=7.70 Hz), 7.45-7.64 (2H, m), 7.21-7.42 (2H, m), 7.03 (1H, d, J=7.92 Hz), 6.90-6.99 (2H, m), 6.45 (1H, dd, J=8.58, 2.20 Hz). Mass spectrum m/z 321.0 (M+H)+.

Aufarbeitung

  1. waitAfter 16 h
  2. stirringthe mixture was stirred for 1 h
  3. customthe organic solvent was removed under vacuum
  4. additionThe aqueous residue was diluted with water
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-842899c254574e248980c4ce3e2b8e49
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084620B2

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