Stability of Sulpyrine. V. Oxidation with Molecular Oxygen in the Solid State

概要

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The solid-state decomposition of sulpyrine was investigated at 80° under oxygen gas. The initial rate of decomposition depended on the water content. When the amount of water present was insufficient to dissolve all the sulpyrine, the rate was of zero-order and increased in proportion to the amount of water. On the other hand, in the presence of a larger amount of water, sulpyrine decomposed in an apparent first order reaction, but the rate was dependent on the amount of water. It is proposed as a mechanism that sulpyrine is hydrolyzed to 4-methylaminoantipyrine (MAA), and then MAA is further oxidized in the aqueous layer. The first order rate constant of decomposition of MAA estimated in saturated solution of sulpyrine in the presence of solid phase was in good agreement with that estimated in sulpyrine solution of lower concentration. As reaction products, aminopyrine (Am), 4-aminoantipyrine (AA), 4-formylaminoantipyrine (FAA) and 4-formylmethylaminoantipyrine (FMAA) were identified. It is proposed that Am and AA may be formed from MAA by methyl rearrangement, while FAA and FMAA may be formed from MAA and Am, respectively, by oxidation of the methyl to a formyl group via intermediates.
社団法人日本薬学会の論文
1979-10-25