1-(2-fluoro-4-nitrophenyl)-1H-imidazole → 3-fluoro-4-(1H-imidazol-1-yl)aniline

HRID 1802012Notes

Reaction equation

HRID 1802012 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][N:13]=[CH: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][N:13]=[CH:12]1

Participants

4

Reactant 1

HCID 53061531-(2-fluoro-4-nitrophenyl)-1H-imidazole

Product 1

HCID 103749763-fluoro-4-(1H-imidazol-1-yl)anilineYield 88.5%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 23938PalladiumCatalyst

Procedure

A mixture of 1-(2-fluoro-4-nitrophenyl)-1H-imidazole (1.81 g, 8.74 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-imidazol-1-yl)benzenamine as a solid (1.37 g). MS178.3 (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-ba7a3d2679274d2493f6c090e38e9731
Source dataset
uspto-grants-2013_01
Patent number
US08349860B2

Reaction notes

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