2,2'-Bipyridine → 2-Pyridinecarboxylic acid, 4,5,6-trichloro-

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An 8 mL scintillation vial was charged with NiCl2.6H2O (12.0 mg, 0.051 mmol) and 2,2′-bipyridine (17.0 mg, 0.109 mmol). The vial was closed and purged with nitrogen for 5 min, after which the vial was charged with DMF (4.5 mL) and isopropyl alcohol (iPrOH; 0.5 mL). The mixture was allowed to stir for 5 min. To the vial was added zinc dust (0.2194 g, 3.4 mmol), and the mixture was allowed to stir under nitrogen for 35 min. Solid 3,4,5,6-tetrachloropicolinic acid (0.1076 g, 0.4 mmol) was added through the top of the reactor. The reaction mixture was allowed to stir at 14° C. and samples were removed periodically to determine reaction kinetics. The samples (˜0.01 mL of reaction mixture diluted to 1.5 mL with acetonitrile) were analyzed by a calibrated HPLC method.

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