Sodium Hydroxide → 1-Phenyl-1H-pyrazol-4-amine

HRID 1802049Notes

Reaction equation

HRID 1802049 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)([O-])=O.[OH-].[Na+]>CCOC(C)=O>[C:9]1([N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27558944-nitro-1-phenyl-1H-pyrazole

Product 1

HCID 1210211-Phenyl-1H-pyrazol-4-amineYield 46.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitro-1-phenyl-1H-pyrazole (440 mg, 2.32 mmol) and SnCl2 dihydrate (2.18 g, 9.66 mmol) in EtOAc (15 mL) was stirred at 80 C for 3 h. Aqueous 1N NaOH was added to bring pH to 12. The mixture was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-phenyl-1H-pyrazol-4-amine as a solid (173 mg).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-6ed53364032646d793dbbee163994e82
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

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