Ammonium Chloride → 5-Chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine

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Reaction Steps

2-Chloro-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine (0.64 g, 2.112 mmol) was dissolved in methanol (50 mL) and THF (50.0 mL). Ammonium chloride (1.130 g, 21.12 mmol) was added, followed by zinc dust (1.381 g, 21.12 mmol). The suspension stirred at room temperature for 3 hours and was then filtered through Celite® and evaporated to yield a brown solid, which was then partitioned between a 4:1 mixture of ethyl acetate and THF (150 mL) and water (75 mL). The organic layer was washed with brine, dried over magnesium sulfate, and evaporated to afford 5-chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine (0.505 g, 88% yield) as a thick brown oil. MS (ESI) m/z: 273.0 (M+H+).

Provenance & Evidence