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

HRID 1061816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061816
[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%). δH (400 MHz, CDCl3) 3.65 (2H, br s), 6.68 (1H, m), 6.98 (1H, dd, J 8.6, 11.0), 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-bf8a0398a25a45cd899f93a42ca27ed9
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960598B2

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