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

HRID 604863

Reaktionsgleichung

Reaktionsgleichung von HRID 604863
[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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cdfdc24091ba44b497bd55592611929c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910740B2

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