4-nitro-1-{3-(trifluoromethyl)phenyl}-1H-imidazole → 1-(3-(trifluoromethyl)phenyl)-1H-imidazol-4-amine

HRID 2409859Notes

Reaction equation

HRID 2409859 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH:8]=1)([O-])=O>CO.[Pd]>[F:18][C:15]([F:16])([F:17])[C:11]1[CH:10]=[C:9]([N:7]2[CH:8]=[C:4]([NH2:1])[N:5]=[CH:6]2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 532316494-nitro-1-{3-(trifluoromethyl)phenyl}-1H-imidazole

Product 1

HCID 665207271-(3-(trifluoromethyl)phenyl)-1H-imidazol-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a 100-mL round bottom flask, was placed a solution of 4-nitro-1-(3-(trifluoromethyl)phenyl)-1H-imidazole (1.5 g, 5.54 mmol, 1.00 equiv, 95%) in methanol (30 mL). The mixture was treated with Pd/C (1.5 g) and stirred under a hydrogen atmosphere for 4 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 1.2 g (88%) of 1-(3-(trifluoromethyl)phenyl)-1H-imidazol-4-amine as a brown oil.

Workup

  1. customInto a 100-mL round bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. customThis resulted in 1.2 g (88%) of 1-(3-(trifluoromethyl)phenyl)-1H-imidazol-4-amine as a brown oil

Sources & evidence

ORD record
ord-bf1eb847ca7548eca1870fde38f64390
Source dataset
uspto-grants-2014_08
Patent number
US08815910B2

Reaction notes

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