2-Methyl-1-(4-nitro-2-(trifluoromethyl)phenyl)-1H-imidazole → 4-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)aniline

HRID 1968420Notes

Reaction equation

HRID 1968420 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=2[C:16]([F:19])([F:18])[F:17])[CH:4]=[CH:5][N:6]=1>C(O)C.[Pd]>[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=2[C:16]([F:19])([F:17])[F:18])[CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 1

HCID 598224512-Methyl-1-(4-nitro-2-(trifluoromethyl)phenyl)-1H-imidazole

Product 1

HCID 549354784-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-methyl-1-(4-nitro-2-trifluoromethyl-phenyl)-1H-imidazole (6.0 g, 22.1 mmol) is dissolved in ethanol (100 mL). After hydrogenation catalyzed by palladium (10 wt % on activated carbon, wet, Degussa type, 1 g) under 1 atm H2 balloon for overnight, the reaction mixture is filtered through a pad of celite and washed with ethanol. The combined filtrate and washings are concentrated to afford the title compound, which is used for next reaction without any further purification.

Workup

  1. filtrationthe reaction mixture is filtered through a pad of celite
  2. washwashed with ethanol
  3. concentrationThe combined filtrate and washings are concentrated

Sources & evidence

ORD record
ord-709fd84e1222425e91a4581e81f6a983
Source dataset
uspto-grants-2013_04
Patent number
US08426404B2

Reaction notes

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