5'-Fluoro-5-nitro-3,3'-bipyridin-4-amine → 5'-Fluoro-3,3'-bipyridine-4,5-diamine

HRID 1916478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916478
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([N+:15]([O-])=O)[C:13]=2[NH2:14])[CH:5]=[N:6][CH:7]=1>CCO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([NH2:15])[C:13]=2[NH2:14])[CH:5]=[N:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 867010655'-Fluoro-5-nitro-3,3'-bipyridin-4-amine

Produkt 1

HCID 867010665'-Fluoro-3,3'-bipyridine-4,5-diamineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 5′-fluoro-5-nitro-3,3′-bipyridin-4-amine (LXXI) (621 mg, 2.65 mmol) in EtOH (18 mL) was added 10% Pd/C (93 mg, 15% by wt). The solution was purged with hydrogen and stirred for overnight at room temperature under hydrogen. The suspension was filtered through Celite and concentrated under vacuum. The crude product was purified through a silica gel column (100% CHCl3→3:97MeOH[7N NH3]:CHCl3) to produce 5′-fluoro-3,3′-bipyridine-4,5-diamine (LXII) as an off-white solid (542 mg, 2.65 mmol, 100% yield). 1H NMR (DMSO-d6, 500 MHz) δ ppm 4.78 (brs, 2H), 5.28 (brs, 2H), 7.46 (s, 1H), 7.70 (s, 1H), 7.73-7.76 (m, 1H), 8.44-8.45 (m, 1H), 8.56 (d, J=2.8 Hz, 1H); ESIMS found C10H9FN4 m/z 205 (M+H).

Aufarbeitung

  1. customThe solution was purged with hydrogen
  2. filtrationThe suspension was filtered through Celite
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified through a silica gel column (100% CHCl3→3:97MeOH[7N NH3]:CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-8eba511313e5415e90f57fd82ab34ac4
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618128B1

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