1-(2-fluoro-4-nitrophenyl)-1H-pyrazole → [3-fluoro-4-(1H-pyrazol-1-yl)phenyl]amine

HRID 1846688Notes

Reaction equation

HRID 1846688 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[N:12]1

Participants

4

Reactant 1

HCID 107035141-(2-fluoro-4-nitrophenyl)-1H-pyrazole

Product 1

HCID 10725981[3-fluoro-4-(1H-pyrazol-1-yl)phenyl]amineYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 23938PalladiumCatalyst

Procedure

A suspension of 1-(2-fluoro-4-nitrophenyl)-1H-pyrazole (1.80 g, 8.70 mmol) and Pd—C (10%, 0.200 g) in MeOH (20 mL) (containing 10 drops of 6N HCl) was hydrogenated under balloon H2 overnight. The mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dried on vacuum to give 3-fluoro-4-(1H-pyrazol-1-yl)benzenamine as a solid (1.55 g). MS 178.3 (M+H)

Workup

  1. customwas hydrogenated under balloon H2 overnight
  2. filtrationThe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was dried on vacuum

Sources & evidence

ORD record
ord-a677fa2654ed4787a85268b1ef044844
Source dataset
uspto-grants-2015_02
Patent number
US08952027B2

Reaction notes

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