2-chloro-3-nitro-6-phenylpyridine

A 20 L jacketed reactor equipped with temperature probe, nitrogen inlet and reflux condenser was charged with acetonitrile (6.0 L, 5 vol.) followed by 1a (1.2 kg, 5.5 mol.) and then POCl(7) A 3 L, three-neck RB flask equipped with a stirrer, argon inlet, reflux condenser and thermometer was charged with acetonitrile (1500 mL), Cu(I)Cl (59.7 g, 604.0 mmol) and tert-butyl nitrite (112.2 mL, 929 mmol). The mixture was heated to 40-50° C. and 1 (100.0 g, 467.3 mmol) was then added in portions. The resulting mixture was stirred at 40-50° C. for one hour and the reaction was deemed complete by HPLC. The reaction was quenched with aqueous ammonium chloride solution (2.0 L, 20 vol.) and diluted with MTBE (2.0 L, 20 vol.). The organic layer was removed and the aqueous layer was extracted with MTBE (2×1 L, 20 vol.). The combined organic layers were treated with charcoal and heated to 50° C. The hot solution was filtered through a pad of Celite® and the Celite® pad was washed with hot MTBE (1 L, 1 vol.), dried over sodium sulfate and concentrated to give crude 1′ (61.1 g, 60.7percent). The crude compound was triturated in methanol (183 mL, 3 vol. with respect to crude weight) for 15 minutes. The solids were filtered, washed with methanol (30 mL) and dried to obtain 1′ (48.0 g, 43.4percent). This was triturated with heptanes (100 mL, 1 vol.) at ambient temperature for one hour, filtered and washed with heptanes (25 mL) and dried to give 1′ as yellow solid (42.02 g, 38.5percent, 97.6percent purity). The compound was characterized by

Molecular Weight:234.64
XLogP3:3.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:234.0196052
Monoisotopic Mass:234.0196052
Topological Polar Surface Area:58.7
Heavy Atom Count:16
Complexity:251
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes