Synthesis of diazo dyes

CHED 483

Jessica L. Ketron, jlketron09@transy.edu, Mallory J. Harlow, mjharlow09@transy.edu, and Gerald Seebach, gseebach@transy.edu. Division of Natural Science & Mathematics, Transylvania University, 300 N. Broadway, Lexington, KY 40508
Previously, 11 diazo dyes were synthesized in this laboratory and reacted with copper(II), cobalt(II), nickel(II), and zinc(II) to form metal diazo complexes. Each of the dyes had a β-naphthoate bonded through a diazo linkage to an aniline ring, with varying functional groups on the ring, to form a tridentate ligand. A series of four pyridine compounds, 2-aminopyridine, 2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine, are the starting materials used to synthesize the new diazo dyes. The synthesis of these diazo compounds are reported and the metal, copper or zinc, complexes are prepared by addition of the metal chloride. The metal complex solutions and pure dyes are analyzed utilizing mass spectrometry, IR, UV-VIS, and NMR to determine the point of attachment of the metal to the ligand.