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

HRID 1880266Notes

Reaction equation

HRID 1880266 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-3c39336084354351b366869695137bdc
Source dataset
uspto-grants-2012_11
Patent number
US08318755B2

Reaction notes

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