2015. 56, 5 – UDC 541.6:547.13:546.49 X-RAY STRUCTURE OF AN AMIDE-APPENDED CHLOROMERCURATED DERIVATIVE OF 2-PHENYLQUINOLINE C.-Y. Lin, W. Henderson, B.K. Nicholson Department of Chemistry, School of Science, University of Waikato, Hamilton, New Zealand E-mail: w.henderson@waikato.ac.nz Received February, 03, 2014 Reaction of the morpholine amide derivative of 2-phenyl-4-quinolinecarboxylic acid with mercury(II) acetate and lithium chloride results in chloromercuration at the ortho position on the phenyl ring; the complex was characterised by ESI mass spectrometry and an X-ray structure determination. <...> INTRODUCTION Organomercury compounds have found to be versatile reagents for the synthesis of a wide range of cycloaurated gold(III) complexes through transmetallation reactions [ 1 ]. <...> The transmetallation synthesis of cycloaurated gold complexes has been applied to a wide range of systems, including substituted pyridines, azobenzenes, oxazolines, and N,N-dimethylbenzylamines among others [ 1, 2 ]. <...> One of the precursors that has been orthomercurated and converted to a cycloaurated gold complex is the methyl ester of 2-phenyl-4-quinolinecarboxylic acid 1 [ 3 ]. <...> To date, only the methyl ester of 2-phenyl-4-quinolinecarboxylic acid has been converted (via orthomercurated precursor 2) into cycloaurated gold(III) complex 3. <...> In this paper, the feasibility of orthomercurating amide derivatives is exemplified by the synthesis and structural characterization of a mercurated morpholine derivative of 2-phenyl-4-quinolinecarboxylic acid 1. <...> Elemental microanalyses were from the Campbell Microanalytical Laboratory, University of Otago. 2-Phenyl-4-quinolinecarboxylic acid (Aldrich), mercury(II) acetate (BDH), lithium chloride (BDH), morpholine (Aldrich), and thionyl chloride (Riedel de Hдen) were used as supplied. <...> The following reaction was carried out using a Schlenk line with a supply of dry nitrogen gas. 2-Phenyl-4-quinolinecarboxylic acid 1a (3.28 g, 13.2 mmol) was refluxed in thionyl chloride (5 ml, excess) for 1 h. <...> All non-hydrogen atoms were treated anisotropically and hydrogen atoms were included with a riding model with d(C—H) 0.95 Е, Uiso = = 1.2Ueq(C) for aromatic hydrogen atoms. <...> RESULTS AND DISCUSSION 2-Phenyl-4-quinolinecarboxylic acid 1 was converted into its morpholine amide derivative 4 by a two-step procedure involving conversion to the acid chloride, followed by reaction with excess morpholine, as summarised <...>