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

HRID 1176020Notes

Reaction equation

HRID 1176020 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

1 g of sodium nitrite (27.6 g, 400 mmol) is added portionwise, under argon, 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 maintained below 15° C. and the reaction mixture is then left at ambient temperature overnight, with vigorous stirring. The nitrous vapours are expelled under a stream of argon, and the reaction mixture is then filtered. Washing the solid with H2O followed by purification on silica gel (600 g), elution being carried out according to an elution gradient from CH2Cl2 to a CH2Cl2/EtOAc (9/1) mixture, makes it possible to isolate 1.37 g of product in the form of a brown solid.

Workup

  1. temperatureThe temperature of the reaction mixture is maintained below 15° C.
  2. filtrationthe reaction mixture is then filtered
  3. washWashing the solid with H2O
  4. customfollowed by purification on silica gel (600 g), elution

Sources & evidence

ORD record
ord-49f5b951f5bf476db08728dccd5afbea
Source dataset
uspto-grants-2010_11
Patent number
US07842711B2

Reaction notes

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