Decomposition of Adrenaline and its Analogs by some Mineral Acids. II

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Bibliographic Information

Other Title
  • アドレナリン及びその類縁化合物の酸分解について (第2報)
  • Adnamineの構造研究 その1
  • Studies on the Structure of Adnamine. (1)

Description

Methyladnamine methosulfate (II) was submitted to the Hofmann degradation and crystals (VI) of m.p. 230°, C20H20O4, were obtained. Its catalytic reduction afforded a dihydro compound (VII), m.p. 177°, C20H22O4, possessing four methoxyl groups. The gas evolved during the Hofmann degradation was proved to be trimethylamine by its derivation to chloroaurate. Ozonolysis of (VI) formed formaldehyde which was established as formaldimedone. The infrared absorption spectrum of (VI) exhibited a maximum (in Nujol) at 11.45μ (=C=CH2), which indicates that the amino is present as the terminal group in the side chain. Oxidation of (II) or (VI) with chromium trioxide in glacial acetic acid afforded 2, 3, 6, 7-tetramethoxyanthraquinone (VIII) which was also obtained on oxidation with alkaline potassium permanganate. Since the oxidation of (II) gave 4, 5, 4′, 5′-tetramethoxybenzophenone-2, 2′-dicarboxylic acid (IX), m.p. 245-260°, (II) must be 5-dimethylaminomethyl-2, 3, 6, 7-tetramethoxydibenzo [a, e]-cycloheptatriene methosulfate.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 78 (4), 402-406, 1958

    The Pharmaceutical Society of Japan

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