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

Participants

Reaction Steps

A 100 mL round bottom flask equipped with a magnetic stir bar was charged with NiCl2.6H2O (105 mg, 0.442 mmol), 2,2′-bipyridine (150 mg, 0.960 mmol), DMF (15 mL) and water (2 mL). The resulting mixture was allowed to stir for 5 min, and then zinc dust (2.006 g, 30.7 mmol) was added. The reaction mixture was allowed to stir at ambient temperature for 15 min until a very dark blue/black solution was present. Solid 3,4,5,6-tetrachloropicolinic acid (2.017 g, 7.7 mmol) was added through the top of the reactor. The reaction mixture was allowed to stir at 27° C. for 5.25 h, and the crude reaction mixture was filtered through a course frit filter and washed with DMF (5 mL). The resulting filtrate was diluted with an equal volume of 10% HCl (aq) which resulted in the precipitation of a light yellow solid that was collected by filtration. The solid was collected by vacuum filtration to give the title compound (2.32 g, 81.5%) that was 61.5% pure as analyzed by calibrated HPLC.

Provenance & Evidence