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

HRID 1942869Notes

Reaction equation

HRID 1942869 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1

Participants

4

Reactant 1

HCID 454801801-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazole

Product 1

HCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineYield 78.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1-(2-Methoxy-4-nitro-phenyl)-4-methyl-1H-imidazole (2.52 g, 10.8 mmol) dissolved in ethanol (110 mL) was stirred under an atmosphere of hydrogen at 20° C. for 3.5 h in the presence of 10% palladium on charcoal (0.25 g). The catalyst was filtered off and washed with ethanol. The solvent of the filtrate was evaporated under reduced pressure. The crude product was purified on silica gel using dichloromethane/methanol (19:1 v/v) as eluent. The fraction containing the product was suspended in diethyl ether, stirred for 15 min, filtered and dried to yield the title compound (1.72 g, 78%) as a yellow solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethanol
  3. customThe solvent of the filtrate was evaporated under reduced pressure
  4. customThe crude product was purified on silica gel
  5. additionThe fraction containing the product
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-44659292bcae49849dd65042b4db4634
Source dataset
uspto-grants-2013_03
Patent number
US08389717B2

Reaction notes

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