Ammonium Chloride → 1-(2,4-difluorobenzyl)-1H-indazol-4-amine

HRID 706703Notes

Reaction equation

HRID 706703 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[C:9]([N+:14]([O-])=O)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[Cl-].[NH4+]>[Fe].CCO.O>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([NH2:14])[C:8]=2[CH:7]=[N:6]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 679763271-(2,4-difluorobenzyl)-4-nitro-1H-indazole

Product 1

HCID 679761071-(2,4-difluorobenzyl)-1H-indazol-4-amineYield 75%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 1-(2,4-difluorobenzyl)-4-nitro-1H-indazole (0.142 g, 0.491 mmol), ammonium chloride (0.013 g, 0.245 mmol) in 4:1 v/v EtOH/water (5 mL) was treated with iron (0.274 g, 4.91 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-(2,4-difluorobenzyl)-1H-indazol-4-amine (0.096 mg, 75% yield) as an amber oil.

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-5778833269a84dd5ad61cbabe34f7b81
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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