5-(p-Dimethylaminophenyl)-2, 4-pentadienal as an Analytical Reagent

• Published in: Chemical & pharmaceutical bulletin Vol. 30; no. 7; p. 2467
• Main Authors: NAKATSUJI, SHINICHI, NAKANO, RIE, KAWANO, MIE, NAKASHIMA, KENICHIRO, AKIYAMA, SHUZO
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Science and Technology Agency 01-07-1982
• ISSN: 0009-2363; 1347-5223

5-(p-Dimethylaminophenyl)-2, 4-pentadienal (DAPDA) was conveniently prepared from p-dimethylaminobenzaldehyde by using readily available 4-(tert-butylthio)-3-buten-2-one as the chain lengthening agent. It has been shown that DAPDA is a useful reagent for detection and colorimetric determination of many pharmaceuticals (e.g., ethyl p-aminobenzoate (EAB), procaine hydrochloride, sulfisoxazole, sulfamethoxazole, sodium p-aminosalicylate, etc.) containing primary aromatic amino groups. This method is based on the reaction of these amines with DAPDA in the presence of trichloroacetic acid in methanol to form protonated Schiff bases which can be determined spectrophotometrically in the neighborhood of 630 nm. The limit of detection of these aromatic amines was in the range of 0.05-1.0μg/ml in each case. Lambert-Beer's law holds over 0.2-10μg/ml. The results were comparable to those obtained by hitherto reported methods. The method was successfully applied to commercial preparations of primary aromatic amines.