Reaktion #1518746

Reaktionsgleichung

5-bromo-6′-methoxy-3-nitro-2,3′-bipyridine

tin(II) chloride dihydrate

→

5-Bromo-6′-methoxy-2,3′-bipyridin-3-amine

Lösungsmittel

EtOAc

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONUpon complete addition of the reducing agent
2. 2
   Temperaturthe reaction was cooled to rt
3. 3
   Waschenwashed with 1M NaOH, water, and brine
4. 4
   TrocknenAfter drying over anhydrous sodium sulfate, filtration, and concentration

Vorschrift

To a stirred mixture of 5-bromo-6′-methoxy-3-nitro-2,3′-bipyridine (776.9 mg, 2.50 mmol) in EtOAc (25 mL) was added tin(II) chloride dihydrate (2.83 g, 12.56 mmol) in portions. Upon complete addition of the reducing agent, the mixture was carefully heated to 90° C. After 2 h, the reaction was cooled to rt and diluted with EtOAc, then washed with 1M NaOH, water, and brine. After drying over anhydrous sodium sulfate, filtration, and concentration, the light tan solid was identified as 5-bromo-6′-methoxy-2,3′-bipyridin-3-amine. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.42 (1H, dd, J=2.4, 0.7 Hz), 7.98 (2H, m), 7.34 (1H, d, J=2.0 Hz), 6.90 (1H, dd, J=8.6, 0.7 Hz), 5.49 (2H, s), 3.90 (3H, s).

Quelle