CC1N=C(C2C=CC=C(C)N=2)C=CC=1.CC1C=CN=C(C2C=C(C)C=CN=2)C=1.CC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.Cl[C:45]1[C:46]([C:54]([OH:56])=[O:55])=[N:47][C:48]([Cl:53])=[C:49]([Cl:52])[C:50]=1[Cl:51]>[Zn].C(#N)C>[Cl:51][C:50]1[C:49]([Cl:52])=[C:48]([Cl:53])[N:47]=[C:46]([C:54]([OH:56])=[O:55])[CH:45]=1Three 8 mL scintillation vials were charged with NiCl2.6H2O (12.0 mg, 0.051 mmol) and one of the following ligands: 6,6′-dimethyl-2,2′-bipyridyl, 4,4′-dimethyl-2,2′-bipyridyl or 5-methyl-1,10-phenanthroline (2:1 ligand/metal ratio). The vials were closed and purged with nitrogen for 5 min, after which the vials were charged with DMF (4.5 mL) and water (0.5 mL). The mixtures were allowed to stir for 5 min. To each of the vials was added zinc dust (0.22 g, 3.4 mmol), and the mixtures were allowed to stir under nitrogen for 35 min. Solid 3,4,5,6-tetrachloropicolinic acid (0.10 g, 0.4 mmol) was added to each through the top of the reactor. The reaction mixtures were allowed to stir at ambient temperature, 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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