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

HRID 604863Notes

Reaction equation

HRID 604863 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 78.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2520 mg (10.8 mmol) 1-(2-methoxy-4-nitro-phenyl)-4-methyl-1H-imidazole dissolved in ethanol (110 ml) was hydrated under an atmosphere of hydrogen at room temperature for 3½ hours in the presence of 252 mg of 10% palladium on charcoal. 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 with methylene chloride/methanol 19/1. The fraction containing the product was suspended in diethyl ether, stirred for 15 minutes, filtered and dried to yield 1719 mg (78%) 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine as a yellow solid. MS ISP (m/e): 204.3 (100) (M+H)+. 1H NMR (CDCl3, 250 MHz): δ (ppm)=7.48 (s, 1H), 6.91 (d, 1H), 6.88 (s, 1H), 6.35 (s, 1H), 6.17 (d, 1H), 3.68 (s, 3H), 2.11 (s, 3H).

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 with methylene chloride/methanol 19/1
  5. additionThe fraction containing the product
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-cdfdc24091ba44b497bd55592611929c
Source dataset
uspto-grants-2011_03
Patent number
US07910740B2

Reaction notes

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