2,3-Dichloropyridine is used as a reagent for the preparation of substituted 3-(5-membered heterocycle-carboxamido)pyridine derivatives for treatment of autoimmune and inflammatory diseases. Also in the synthesis, crystal structure and biological activity of novel anthranilic Diamide insecticide with propargyl ether.
Synthesis
2,3-dichloropyridine is synthesized from 2-chloronicotinic acid via amidation, Hofmann degradation, diazotization and Sandmeyer reaction.
Structure and conformation
The complete mol-ecule of 2,3-Dichloropyridine, C5H3Cl2N, is generated by crystallographic twofold symmetry, which forces the pyridine N atom and the opposite C—H group to be statistically disordered. In the crystal, weak aromatic π–π stacking [centroid–centroid separation = 3.805 (4)Å and slippage = 1.704Å] leads to [100] stacks of mol-ecules. Short Cl···Cl contacts [3.334 (3)Å] are also observed. Colourless prisms were grown from ethanol.