Hydrochloric Acid → 6-Bromo-1H-indazole-3-carboxylic acid

HRID 407152

Reaktionsgleichung

Reaktionsgleichung von HRID 407152
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=O)[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.[N:13]([O-])=O.[Na+].S(=O)(=O)(O)O.Cl.[OH2:23].[OH2:24].Cl[Sn]Cl>[OH-].[Na+].O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:7]([OH:24])=[O:23])=[N:13][NH:8]2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 61436Stannous chloride dihydrateHCID 957161H-Indole-2,3-dione, 6-bromo-HCID 23668193Sodium Nitrite

Produkt 1

HCID 247280286-Bromo-1H-indazole-3-carboxylic acidAusbeute 169,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The solution of 6-bromoisatin (10 g, 22 mmol) in 1N aqueous NaOH solution (48 Ml) was stirred at 50° C. for 1 h. The mixture was cooled to 0° C. Sodium nitrite (3 g, 22 mmol) solution in water (11 Ml) was added dropwise for 15 min at 0° C. The mixture was added to the solution of water (90 Ml) and sulfuric acid (4.6 Ml) at 0° C. for 15 min. The mixture was added to the solution of conc. hydrochloric acid (40 Ml) and SnCl2.2H2O (24 g, 53 mmol). After 1 h, the mixture was filtered and washed with water. The solid was dried through air flow to give the titled compound (8.98 g).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. washwashed with water
  3. customThe solid was dried through air flow

Quellen und Nachweise

ORD-Eintrag
ord-ea057a89e8594ee181d07db68154d2d4
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754209B2

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