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

HRID 1801999Notes

Reaction equation

HRID 1801999 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-b2781ea3f4c64cb89b4b7087b1cfe80a
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

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