p-Nitroanilides of amino acids and peptides are widely used as the chromogenic substrates for the determination of the activity of proteolytic enzymes. However, the preparation of a p-nitroanilide is not easy, in part due to the low nucleophilicity of the amino group of p-nitroaniline. A facile preparation of p-nitroanilide analog by the solid-phase method was investigated. 5-Amino-2-nitrobenzoic acid (Anb^{5, 2}) was used instead of p-nitroaniline (pNA) for preparation of p-nitroanilide analogs. Anb^{5, 2} was introduced on a p-methylbenzhydrylamine resin without protection of the amino group of Anb^{5, 2} by the 2-(H-benzotriazol-1-yl)-1, 1, 3, 3-tetramethyluronium tetrafluoroborate (TBTU) method in the presence of p-dimethylaminopyridine. The coupling reaction of a N^α-, N^G-protected arginine with a Anb^{5, 2}-resin was difficult to achieve by common coupling methods (such as the carbodiimide and diphenylphosphoryl azide methods), but the phosphoryl chloride method was relatively successful. Synthetic benzoyl-Arg-Anb^{5, 2}-NH₂ and benzoyl-Arg-pNA were hydrolyzed by trypsin and the both reaction mixtures exhibited same spectroscopic characteristics. H-D-Val-Leu-Arg-Anb^{5, 2}-NH₂, an analog of human urine kallikrein substrate, was readily prepared by the solid-phase method. H-Arg-Anb^{5, 2}-OH and H-D-Val-Leu-Arg-Anb^{5, 2}-OH were also synthesized on a Wang resin by the solid-phase method. The aqueous solubility of these free-carboxyl materials was better than those of the corresponding amide analogs. 4-Amino-3-nitrobenzoic acid (Anb^{4, 3}) was also introduced on the p-methybenzhydrylamine resin, but the resulting H-Anb^{4, 3}-resin did not react with N^α-, N^G-protected arginine by any of the coupling methods.