Hydrochloric Acid → 5-Iodo-1H-indazole-3-carbaldehyde

HRID 1454933Notes

Reaction equation

HRID 1454933 reaction equation
[N:1]([O-])=O.[Na+].[I:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.Cl.[OH2:16]>>[I:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:1]=[C:9]2[CH:10]=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27823135-Iodo-1H-indoleHCID 23668193Sodium Nitrite

Product 1

HCID 1785200355-Iodo-1H-indazole-3-carbaldehyde

Procedure

Under argon, 1 g of sodium nitrite (27.6 g, 400 mmol) is added in portions to a suspension of 5-iodoindole (9.722 g, 40 mmol) in water, followed dropwise by a 6N HCl solution (59 ml). The temperature of the reaction mixture is kept under 15° C. and then the reaction mixture is left under vigorous stirring at room temperature overnight. The nitrous vapours are expelled under an argon stream and then the reaction mixture is filtered. Washing the solid with H2O followed by purification on silica gel (600 g), eluting according to an elution gradient from CH2Cl2 to a CH2Cl2/AcOEt (9/1) mixture, makes it possible to isolate 1.37 g of product in the form of a brown solid.

Workup

  1. customis kept under 15° C.
  2. waitthe reaction mixture is left
  3. filtrationthe reaction mixture is filtered
  4. washWashing the solid with H2O
  5. customfollowed by purification on silica gel (600 g)
  6. washeluting

Sources & evidence

ORD record
ord-a02232fd45104f8e851eea5dae92c155
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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