5-Bromoisatin → HCID 178517026, Verbindung

HRID 642119

Reaktionsgleichung

Reaktionsgleichung von HRID 642119
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[N+:13]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([NH:22][NH2:23])=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(O)(=O)C>[N+:13]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([NH:22][N:23]=[C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=3)[NH:7][C:6]2=[O:11])=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]

Komponenten

4

Edukt 2

HCID 68895-BromoisatinHCID 3693744Benzoic acid, 4-nitro-, hydrazide

Produkt 1

HCID 178517026HCID 178517026, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Following the general method as outlined in Example 1, into a suspension of 5-bromo-1H-indole-2,3-dione in acetic acid was added 4-nitrobenzohydrazide. After stirring at 100° C. the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 165 mg of the title compound (85%) as a orange solid in 95.3% purity by HPLC (Rt: 4.80, 5.53, gradient of 10 min, MaxPlot detection between 230 and 400 nm).

Aufarbeitung

  1. temperaturewas cooled to rt
  2. customa yellow solid precipitated out
  3. filtrationFiltration on a fritté
  4. washwashing with AcOH, water
  5. customdrying under vacuo at 60° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-cac3d8e5849e4831b8dbeee0cc0e2f70
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696231B2

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