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

HRID 706829Notes

Reaction equation

HRID 706829 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([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:6]=1>C(O)C.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([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:6]=1

Participants

4

Reactant 1

HCID 587242874-Methyl-1-(2-(trifluoromethyl)-4-nitrophenyl)-1H-imidazole

Product 1

HCID 587242804-(4-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)anilineYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Methyl-1-(2-(trifluoromethyl)-4-nitrophenyl)-1 H-imidazole (1.1 g, 4.1 mmol) was suspended in 50 mL of anhydrous ethanol. The mixture was hydrogenated with 0.11 g of 10% Pd—C at 40 psi for 3 hrs. Then Pd—C was removed by filtration. The filtrate was evaporated to give the title compound 1.0 g as a yellow solid (102.0%). 1H NMR (300 MHz, CDCl3) δ: 7.42 (1 H, s), 7.08-7.11 (1 H, d, J=8.4 Hz), 6.99 (1 H, d, J=2.4 Hz), 6.80-6.84 (1 H, dd, J=2.1 and 8.4 Hz), 6.74 (1 H, s), 4.14 (2 H, brs), 2.27 (3 H, s). LCMS: m/z [M+H]+ 242.0957.

Workup

  1. customThen Pd—C was removed by filtration
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-4ed339b9f3f145249826c06da0069137
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

Loading…