1-(3-Methyl-4-nitrophenyl)-1H-imidazole → 4-(1H-Imidazol-1-yl)-2-methylaniline

HRID 970340Notes

Reaction equation

HRID 970340 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>[Pd]>[N:11]1([C:4]2[CH:5]=[CH:6][C:7]([NH2:8])=[C:2]([CH3:1])[CH:3]=2)[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

3

Reactant 1

HCID 144502461-(3-Methyl-4-nitrophenyl)-1H-imidazole

Product 1

HCID 144502604-(1H-Imidazol-1-yl)-2-methylanilineYield 98%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To 1-(3-methyl-4-nitro-phenyl)-1H-imidazole (200 mg, 0.98 mmol) and 10% Palladium on carbon (35 mg) was added degassed methanol (3 mL). The suspension was flushed and evacuated with hydrogen/vacuum line. The suspension was allowed to stir at room temperature for 14 h under hydrogen atmosphere (hydrogen balloon). The dark reaction mixture was filtered through a pad of celite and rinsed with methanol. Concentration of the filtrate gave the title compound (166 mg, 98%) which was used for the next step without purification. 1H NMR (300 MHz, DMSO-d6) δ 7.95 (1H, s), 7.48 (1H, s), 7.16 (1H, narrow d, J=2.5 Hz), 7.09 (1H, dd, J=2.5, 8.4 Hz), 7.01 (1H, s), 6.67 (1H, d, J=8.4 Hz), 5.03 (2H, broad s), 2,10 (3H, s).

Workup

  1. customdegassed methanol (3 mL)
  2. customThe suspension was flushed
  3. customevacuated with hydrogen/vacuum line
  4. customThe dark reaction mixture
  5. filtrationwas filtered through a pad of celite
  6. washrinsed with methanol

Sources & evidence

ORD record
ord-8b75519de7724a398bdd1d0f39e1c8e9
Source dataset
uspto-grants-2007_12
Patent number
US07312215B2

Reaction notes

Loading…