Ammonia → 4-Fluoro-3-(pyridin-2-yl)aniline

HRID 586253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586253
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[Sn](Cl)Cl.N>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 24479Stannous ChlorideHCID 222853002-(2-Fluoro-5-nitrophenyl)pyridine

Produkt 1

HCID 222853024-Fluoro-3-(pyridin-2-yl)anilineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 2-(2-fluoro-5-nitrophenyl)pyridine (2.11 g, 9.68 mmol) in ethanol (40 ml), stirred in a water bath at 20° C., was added dry tin(II) chloride (7.10 g, 37.3 mmol) portionwise. The mixture was then stirred at room temperature for 18 h. Aqueous ammonia (40 ml of a 25% solution) was added, and the solvent was removed in vacuo, azeotroping with ethanol to remove traces of water. The residue was sequentially boiled in ethyl acetate and filtered three times. The combined filtrates were concentrated in vacuo to yield 4-fluoro-3-(pyridin-2-yl)aniline as a yellow solid (1.54 g, 85%): 1H NMR (400 MHz, CDCl3) δ 3.65 (2H, br s), 6.68 (1H, m), 6.98 (1H, dd, J 8.6, 11.0 Hz), 7.22-7.31 (2H, m), 7.71-7.83 (2H, m), 8.70 (1H, m); MS (ES+) m/z 189 [M+H]+.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customazeotroping with ethanol
  3. customto remove traces of water
  4. filtrationfiltered three times
  5. concentrationThe combined filtrates were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-22a1bf032ce349169b0c038cfbe1778a
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936608B2

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