Ammonium Chloride → 1-phenyl-1H-indazol-4-amine

HRID 706716Notes

Reaction equation

HRID 706716 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-])=O.[Cl-].[NH4+]>[Fe].CCO.O>[C:13]1([N:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[C:5]=3[CH:6]=[N:7]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 249381804-Nitro-1-phenyl-1H-indazole

Product 1

HCID 249380571-phenyl-1H-indazol-4-amineYield 58%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 4-nitro-1-phenyl-1H-indazole (0.140 g, 0.585 mmol), ammonium chloride (0.016 g, 0.293 mmol) in 4:1 v/v EtOH/water (5 mL) was treated with iron (0.327 g, 5.85 mmol) and refluxed for 2 hours. The mixture was concentrated and the residue taken in EtOAc/water, filtered through glass fiber filter paper and concentrated again to provide 1-phenyl-1H-indazol-4-amine (0.071 g, 58% yield) as a beige solid.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe mixture was concentrated
  3. filtrationfiltered through glass fiber
  4. filtrationfilter paper
  5. concentrationconcentrated again

Sources & evidence

ORD record
ord-11e142e49e7a4096b8b7cf8fb959a21b
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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