This work presents the synthesis of hydroxy substituted N-benzimidazole amides using conventional reactions of organic chemistry and microwave-supported synthesis. Acyclic precursors 2, 3 and 4 were prepared in microwave-supported amination from 4-chlorine-3-nitrobenzonitrile 1 with corresponding amine. In second step of synthesis, acyclic compounds 5, 6 and 7 were prepared by reduction of compounds 2, 3 and 4 with SnCl2×2H2O. Main precursors 8, 9 and 10, 2-a,inosubstituted benzimidazoles were synthesized by cyclocondensation of compounds 5, 6 and 7 with BrCN. Methoxy substituted derivatives 13, 14 and 16 were prepared in condensation reaction of compounds 8, 9, 10 and 11 and 2,4-dimethoxybenzoyl-chloride with triethylamine. Targeted compounds 17, 18 and 19 were synthesized by removal of protecting groups of compounds 13, 14 and 16 in reaction with BBr3 on a low temperature, with successful removal of only one protecting group. In the second synthetic pathway for the synthesiy of dihydroxy substituted derivatives, precursor 21 was prepared by reaction of benzylation 2,4-dihydroxy benzoic acid 20 with benzyl-chloride, while precursor 22 obtained by debenzylation of carboxyl group of compound 21 with NaOH. Targeted product 24 was prepared in condensation reaction in the presence of triethylamine from compound 11 and compound 23, previously prepared from compound 22 by halogenation of carboxyl group using SOCl2. Structures of synthesized compounds were confirmed with 1H, 13C and 2D NMR spectroscopy. Antioxidative activity of prepared compounds was examined by using DPPH nad FRAP methods.