5-chloro-4-nitro-1H-indazole → 5-Chloro-1H-indazol-4-amine

HRID 1443218Notes

Reaction equation

HRID 1443218 reaction equation
[Cl:1][C:2]1[C:3]([N+:11]([O-])=O)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2>[Pd]>[Cl:1][C:2]1[C:3]([NH2:11])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2

Participants

3

Reactant 1

HCID 179892685-chloro-4-nitro-1H-indazole

Product 1

HCID 179892615-Chloro-1H-indazol-4-amine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution that consists of 5-chloro-4-nitro-1H-indazole (872 mg, 4.41 mmol) is mixed with 150 mg of palladium on carbon (10%) and stirred under hydrogen atmosphere at room temperature. After 45 minutes, the catalyst is suctioned off on one frit and washed with methanol. The filtrate is concentrated by evaporation, and the residue is taken up in 200 ml of ethyl acetate and heated. After renewed suctioning-off and concentration by evaporation of the filtrate, the purification on silica gel is carried out with hexane/ethyl acetate (100-33% hexane). 296 mg (40% of theory) of the product is obtained.

Workup

  1. washwashed with methanol
  2. concentrationThe filtrate is concentrated by evaporation
  3. temperatureheated
  4. concentrationconcentration
  5. customby evaporation of the filtrate
  6. customthe purification on silica gel
  7. custom296 mg (40% of theory) of the product is obtained

Sources & evidence

ORD record
ord-424bf2fa532a4977a99e05ef36b66080
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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