総合感冒剤中の主成分の定量法に関する研究(第5報) : 1,2-ナフトキノン-4-スルホン酸カリウムによるスルピリンおよび第2級アミンの呈色反応機構について

概要

論文の詳細を見る
A mechanism of color reaction of sulpyrine and secondary amines by potassium 1,2-naphthoquinone-4-sulfonate has been studied. Reaction products of potassium 1,2-naphthoquinone-4-sulfonate with sulpyrine, 4-methylaminoantipyrine, 4-aminoantipyrine, N-methylaniline, and N-methylbenzylamine were isolated by extraction with chloroform, followed by alumina chromatography, and recrystallization. Structures of these color reaction products were investigated by elementary and N-methyl analysis, nuclear magnetic resonance spectra, and visible absorption spectra. On the basis of these data, reaction mechanism of coloration of sulpyrine was considered as the initial hydrolysis of sulpyrine to 4-methylaminoantipyrine, attack of potassium 1,2-naphthoquinone-4-sulfonate on nitrogen atom in the 4-position of 4-methylaminoantipyrine as an electrophilic reagent to form addition product of 1,2-naphthoquinone-4-sulfonate tentatively, and desulfonation to give N-methyl-N-(1,2-naphthoquino-4-yl)-4-aminoantipyrine as a pigment quantitatively. In the same way as sulpyrine, mechanism of color reaction of N-methylaniline by potassium 1.2-naphthoquinone-4-sulfonate was found to be the initial reaction of 1,2-naphthoquinone-4-sulfonate with N-methylaniline to form 4-(N-methylanilino)-1,2-naphthoquinone as the consequence of desulfonation. Coloration of other aromatic and aliphatic secondary amines was investigated, and secondary amines were found to react generally with potassium 1,2-naphthoquinone-4-sulfonate to form colored substances. Mechanisms of these colorations have been interpreted in terms of electronic theory.
公益社団法人日本薬学会の論文
1967-04-25

総合感冒剤中の主成分の定量法に関する研究(第5報) : 1,2-ナフトキノン-4-スルホン酸カリウムによるスルピリンおよび第2級アミンの呈色反応機構について

スポンサーリンク

概要

著者

関連論文

スポンサーリンク