1-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole → 2-Fluoro-4-(1,2,4-triazol-1-yl)phenylamine

HRID 2299206

Reaktionsgleichung

Reaktionsgleichung von HRID 2299206
[F:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(O)C.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:3][C:2]=1[F:1]

Komponenten

4

Edukt 1

HCID 218839191-(3-fluoro-4-nitrophenyl)-1H-1,2,4-triazole

Produkt 1

HCID 218838662-Fluoro-4-(1,2,4-triazol-1-yl)phenylamineAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

1-(3-Fluoro-4-nitrophenyl)-1H-1,2,4-triazole (3.06 g) was dissolved in ethanol (100 ml) and admixed with 10% Pd/C (50% water, 612 mg) and then stirred under a hydrogen atmosphere at room temperature for 1 hour. After filtering the catalyst off, the filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate, and the resultant solution as washed successively with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:2). A desired fraction was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to yield 1-(4-amino-3-fluorophenyl)-1H-1,2,4-triazole (1.68 g) as yellow powdery crystals.

Aufarbeitung

  1. filtrationAfter filtering the catalyst off, the filtrate
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washthe resultant solution as washed successively with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:2)
  8. concentrationA desired fraction was concentrated under reduced pressure
  9. customthe residue was crystallized from a mixture of ethyl acetate and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b70b8a07105d416b8fe25803d4567585
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495604B1

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