The synthesis and characterization of some novel 5-chloro-2-(substituted alkoxy)-N-phenylbenzamide derivatives

• Published in: Journal of the Serbian Chemical Society Vol. 74; no. 8-9; pp. 847 - 855
• Main Authors: Ienaşcu, Ioana, Lupea, Alfa, Popescu, Iuliana, Pădure, Mirabela, Zamfir, Alina
• Format: Journal Article
• Language: English
• Published: Serbian Chemical Society 2009
• Subjects: 5-chloro-2-(substituted alkoxy)-n-phenylbenzamide derivatives; ethyl esters; hydrazides; hydrazones; o-substituted salicylanilides
• ISSN: 0352-5139; 1820-7421
• DOI: 10.2298/JSC0909847I

To obtain biologically active compounds, the synthesis of some new derivatives with an o-hydroxybenzamide structure was performed. The ethyl esters 4-6 were obtained by the reaction of 5-chloro-2-hydroxy-N-phenylbenzamide and chloro-substituted acid ethyl esters 1-3 in ethyl methyl ketone. The obtained ethyl esters were condensed with hydrazine yielding the hydrazides 7-8. The hydrazones 11-14 were obtained by the reaction of the hydrazides and the chloro-substituted benzaldehydes 9-10. All the newly synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, MS and elemental analyses. U cilju dobijanja bioloski aktivnih jedinjenja izvrsena je sinteza nekih novih deri- vata o-hidroksibenzamida. Etil-estri su dobijeni reakcijom N-fenil-2-hidroksi-5-hloro-benzamida i hloro-supstituisanih etil-estara 1-3 u etil-metil-ketonu. Dobijeni etil-estri kondenzovani su sa hidrazinom gradeci hidrazide 7 i 8. Hidrazoni 11-14 su zatim dobijeni reakcijom hidrazida sa hloro-supstituisanim benzaldehidima 9 i 10. Nova jedinjenja su okarakterisana pomocu FTIR, 1H-NMR, 13C-NMR, MS i elementalnom analizom.