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

HRID 558993Notes

Reaction equation

HRID 558993 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-3fd49d404bc949c092c67c1e0d49e0b0
Source dataset
uspto-grants-2011_11
Patent number
US08063058B2

Reaction notes

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