Ammonium Hydroxide → HCID 70497940, compound

Participants

Reaction Steps

Ammonium hydroxide (NH4OH) was added to crude 4,5,6-trifluoropicolinonitrile (2.5 g, 15.8 mmol) and stirred at room temperature for 2 h. A brown solid formed which was filtered, washed with water and dried to give 0.72 g. Analysis by gas chromatography-mass spectroscopy (GC-MS) indicated the presence of two isomeric products. The aqueous filtrate was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, and evaporated to give additional brown solid. The two crops were combined and purified by silica gel chromatography to give 4-amino-5,6-difluoro-picolinonitrile (0.60 g, 24.4%): 1H NMR (400 MHz, CDCl3) δ 7.13 (d, J=5.3 Hz, 1H, aromatic), 6.62 (s, 2H, NH2); 13C NMR (101 MHz, CDCl3) δ 157.0 (dd, J=235, 12 Hz), 151.7 (dd, J=10, 7 Hz), 139.5 (dd, J=254, 29 Hz), 128.8 (d, J=19 Hz), 121.2 (s), 121.0 (s); 19F NMR (376 MHz, CDCl3) δ −85.29 (d, J=24.5 Hz), −156.98 (dd, J=24.5, 5.2 Hz).

Provenance & Evidence