Sodium Nitrite → 6-bromo-5-chloro-1H-indazole

HRID 2203219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2203219
[Br:1][C:2]1[C:3]([Cl:10])=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[N:11]([O-])=O.[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:8]=[C:6]2[C:5]([CH:9]=[N:11][NH:7]2)=[CH:4][C:3]=1[Cl:10]

Komponenten

5

Edukt 2

HCID 23668193Sodium NitriteHCID 467382955-Bromo-4-chloro-2-methylaniline

Produkt 1

HCID 748904626-bromo-5-chloro-1H-indazoleAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To 5-bromo-4-chloro-2-methylaniline (1 g, 4.54 mmol) in acetic acid (10 mL) was added a solution of sodium nitrite (0.329 g, 4.76 mmol) in water (1 mL). The mixture was heated at reflux for 2 hours and was subsequently cooled and concentrated. The residue was partitioned in water and extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to give the title compound as a red-brown solid (0.67 g, 64%). ESI-MS m/z [M+H]+ 232.2.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperaturewas subsequently cooled
  4. concentrationconcentrated
  5. customThe residue was partitioned in water
  6. extractionextracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b4940dc236604863af7af5a7ea80f67f
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365566B2

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