Hydrazine hydrate (1:1) → 4-(3-Fluoropyridin-4-yl)aniline

HRID 1510237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510237
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1.O.NN>C(O)C.Cl[Fe](Cl)Cl>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 690819133-Fluoro-4-(4-nitrophenyl)pyridine

Produkt 1

HCID 690819074-(3-Fluoropyridin-4-yl)anilineAusbeute 70,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24380Iron chloride (FeCl3)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a refluxing mixture of 3-fluoro-4-(4-nitrophenyl)pyridine (2.23 g), trichloroiron (130 mg) and activated carbon (1.12 g, 50 wt % of the starting material) in ethanol (74 mL) was added dropwise hydrazine hydrate (1.6 g), and the mixture was stirred for 3 hours. The insoluble materials were removed by filtration in hot and washed with ethanol. Most of ethanol was removed in vacuo, and to the residue was added water. Resulting solid was collected by filtration, and purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:2) to afford 4-(3-fluoropyridin-4-yl)aniline (1.36 g) a pale orange solid.

Aufarbeitung

  1. customThe insoluble materials were removed by filtration in hot and
  2. washwashed with ethanol
  3. customMost of ethanol was removed in vacuo
  4. additionto the residue was added water
  5. customResulting solid
  6. filtrationwas collected by filtration
  7. custompurified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-b9434d01266c483dad4bebf1b35dc25f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211919B2

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