Water → 1-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amine

HRID 524995Notes

Reaction equation

HRID 524995 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[Cl-].[NH4+].O.C(OCC)(=O)C>C(O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 666114661-(4-Methoxybenzyl)-4-nitro-1H-pyrazole

Product 1

HCID 283739871-((4-methoxyphenyl)methyl)-1H-pyrazol-4-amineYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

1-(4-Methoxybenzyl)-4-nitro-1H-pyrazole (2.17 g, 9.30 mmol) was dissolved in ethanol (20 ml). Ammonium chloride (50 mg, 0.93 mmol) and iron (powder, 2.60 g, 46.56 mmol) were added and the mixture was refluxed for 1 h. The reaction mixture was filtered through Celite® and the solvent was evaporated to dryness under reduced pressure. Usual work-up with water and ethyl acetate afforded 1.77 g (94% yield) of the title compound as an oil, which was used in the next synthetic step without further purification.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. filtrationThe reaction mixture was filtered through Celite®
  3. customthe solvent was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2d07514a76fd4abd90e4e93583c85058
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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