Sulfuric Acid → 5-Iodo-1H-indazole-3-carboxylic acid

HRID 1454929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454929
[I: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.[OH-:13].[Na+].[N:15]([O-])=O.[Na+].S(=O)(=O)(O)O.[Sn](Cl)(Cl)(Cl)Cl>O>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:15]=[C:5]2[C:6]([OH:11])=[O:13]

Komponenten

7

Edukt 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 886955-IodoisatinHCID 23668193Sodium Nitrite

Produkt 1

HCID 218135505-Iodo-1H-indazole-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-Iodoisatin (5 g, 18.3 mmol) is heated in the presence of sodium hydroxide (0.77 g, 19.2 mmol in 12 ml H2O) until dissolution is obtained and then the reaction mixture is cooled to 0° C. A sodium nitrite solution cooled beforehand to 0° C. (1.26 g, 18.3 mmol in 5.5 ml H2O) is added. The paste obtained is added in small portions, with vigorous stirring, to a sulphuric acid solution (3.40 g, 34.8 mmol in 37 ml H2O) precooled to 0° C. so that the temperature does not exceed 4° C. The stirring is maintained for 15 min and then a tin chloride solution (SnCl2.2H2O, 9.91 g, 43.9 mmol in 15 ml concentrated HCl) is slowly added such that the temperature does not exceed 4° C. The medium is allowed to react for several hours. The reaction mixture is filtered. The solid is washed with boiling water and then taken up in ethanol in the hot state. The insoluble impurities are removed by filtration.

Aufarbeitung

  1. customis obtained
  2. custombeforehand to 0° C.
  3. additionis added
  4. customThe paste obtained
  5. customprecooled to 0° C. so that the temperature
  6. customdoes not exceed 4° C
  7. temperatureThe stirring is maintained for 15 min
  8. customdoes not exceed 4° C
  9. customto react for several hours
  10. filtrationThe reaction mixture is filtered
  11. washThe solid is washed with boiling water
  12. customThe insoluble impurities are removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c09e2439d5834a6ca9dda9d72771dd5b
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482342B2

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