HCID 10593300, Verbindung → 2-Amino-4,6-dibromo-3-hydroxybenzoic acid

HRID 259926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 259926
[Br:1][C:2]1[CH:10]=[C:9]([Br:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-])=O)[C:3]=1[OH:15]>CCO>[Br:1][C:2]1[C:3]([OH:15])=[C:4]([NH2:12])[C:5](=[C:9]([Br:11])[CH:10]=1)[C:6]([OH:8])=[O:7]

Komponenten

3

Edukt 1

HCID 10593300HCID 10593300, Verbindung

Produkt 1

HCID 99048002-Amino-4,6-dibromo-3-hydroxybenzoic acidAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

4,6-Dibromo-3-hydroxy-2-nitrobenzoic acid (4.09 g, 12 mmol) and PtS2 (160 mg, 0.62 mmol) in EtOH (150 mL) was hydrogenated at atmospheric pressure and room temperature for 45 h. Filtration and evaporation of the filtrate gave a crude product (3.69 g) which was purified by flash chromatography (SiO2, toluene-EtOAc). Treatment with activated charcoal in MeOH and crystallization from MeOH/H2O gave the title compound (2.51 g). Mp: 162°-164.5° C. 1H NMR (DMSO-d6): δ6.96 (s, 1H). 13C NMR (DMSO-d6): δ167.69, 140.56, 139.95, 121.81, 117.23, 112.53, 110.45. MS (EI, 70 ev): m/z (rel. int.) 309, 311, 313 (M+, 36, 72, 34).

Aufarbeitung

  1. filtrationFiltration and evaporation of the filtrate
  2. customgave a crude product (3.69 g) which
  3. customwas purified by flash chromatography (SiO2, toluene-EtOAc)
  4. customTreatment with activated charcoal in MeOH and crystallization from MeOH/H2O

Quellen und Nachweise

ORD-Eintrag
ord-758b5b8fc2444b339eefa4f8a616ec94
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05523475

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