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

HRID 2075983Notes

Reaction equation

HRID 2075983 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

1-(2-Methoxy-4-nitro-phenyl)-4-methyl-1H-imidazole (2520 mg, 10.8 mmol) dissolved in ethanol (110 mL) was stirred under an atmosphere of hydrogen at room temperature for 3½ hours in the presence of 10% palladium on charcoal (252 mg). 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 minutes, filtered and dried to yield the title compound (1719 mg, 78%) as a yellow solid. MS ISP (m/e): 204.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 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
  5. additionThe fraction containing the product
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-df61f6ca019c46eaa8e0a5fb11b7b8e5
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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