Ammonium Chloride → HCID 68157539, compound

Participants

Reaction Steps

(6-Fluoro-2-(5-fluoropyridin-3-ylamino)-3-nitrobenzonitrile (1.73 g, 6.26 mmol), iron powder (712 mg, 12.5 mmol), and ammonium chloride (966 mg, 18.8 mmol) in methanol (40 mL) and water (12 mL) were heated at 90° C. for 1 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in water and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to yield the title compound as brown solid (948 mg, 61%). 1H NMR 400 MHz δ (CDCl3): 8.05 (1H, d, J=2.4 Hz), 8.03-7.99 (1H, m), 7.01 (1H, d, J=2.1 Hz), 6.99 (1H, s), 6.59 (1H, dt, J=10.2, 2.4 Hz), 5.78 (1H, br s), 3.84 (2H, br s).

Provenance & Evidence