Research in the field of chemistry remains inevitable for the synthesis and manipulation of different drugs and their derivatives. A particular NSAID diclofenac is one of the most widely used drug worldwide. It contains aryl-halo core group in its structure. Altering that core structure with the amide bond formation and thereby assessing its cytotoxic characteristics is the main objective of this study. In order to carry out this task 2-[2-(2,6-dichloroanilino)phenyl]acetate was taken as our starting material which was converted into 2-[2-(2,6-dichloroanilino)phenyl]acetic acid in the first step. After the production of respective carboxylic acid, it was then subjected to amide bond formation by treating it with various substituted anilines using DCC as coupling agent and HOBt as additive in the presence of THF which led to the synthesis of ten different aryl-halo amide derivatives labelled as 4a-j with percentage yields of 82, 84, 81, 82, 80, 83, 81, 79, 83 and 82 respectively. These aryl-halo amide analogues were evaluated for their cytotoxic properties using L929 fibroblast cell line via MTT Assay. The synthesized compounds (4a-j) were shown to have inhibitory concentrations (IC₅₀) of 5.2, 5.3, 5.1, 5.7, 5.0, 5.4, 5.3, 5.9, 5.5, and 5.6 in mM/ml respectively.  Among the compounds assessed 4h was found to be least toxic with an inhibitory concentration (IC₅₀) of 5.9 mM/ml