Ammonium Chloride → 3-Amino-6-fluoro-2-(pyridin-2-ylamino)benzonitrile

Participants

Reaction Steps

6-Fluoro-3-nitro-2-(pyridin-2-ylamino)benzonitrile (1.3 g, 5.0 mmol), iron powder (1.12 g, 20.1 mmol), and ammonium chloride (1.55 g, 30.2 mmol) in methanol (20 mL) and water (7 mL) were heated at 90° C. for 3 h. The reaction mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in water and extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to yield the title compound as a yellow solid (620 mg, 54%). 1H NMR 400 MHz δ (CDCl3): 9.05 (1H, ddd, J=7.5, 1.1, 0.8 Hz), 9.00-8.89 (1H, m), 7.34 (1H, ddd, J=9.1, 6.2, 1.7 Hz), 7.23-7.19 (1H, m), 6.83 (1H, s), 6.80 (1H, d, J=2.8 Hz), 6.65 (1H, ddd, J=7.6, 6.4, 1.4 Hz), 4.53 (2H, br s).

Provenance & Evidence