Synthesis of azo derivatives of 4-aminosalicylic acid

For searching a better 4-aminosalicylic acid derivative with higher activity and less side effects against the inflammatory bowel disease, 4-aminosalicylic acid (4-ASA) was protected by benzyloxycarbonyl and acetyl, respectively. The resultant was hydrogenized to remove protective group of amino group, then the product was reacted with NaNO2 to give diazonium. salt, which was conjugated with salicylic acid, hydroxybenzene, N-salicyloyl glycine acid to get azo derivatives of 4-ASA. The azo derivatives were hydrolyzed under the alkaline condition to get the target products. All compounds were characterized by FT-IR, H-1 NMR, C-13 NMR spectra in details. New derivatives of 4-ASA were characterized. The synthetic route was reasonable and feasible. (C) 2007 Zheng Bao Zhao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.