Adrenochrome誘導体の研究 (第3報)

Adrenochrome類縁化合物の合成 その2 o-Benzoquinone型化合物の合成

抄録

3, 4-Dibenzyloxyaniline was methylated with dimethyl sulfate and sodium hydroxide to N-trimethyl-3, 4-dibenzyloxyanilinium hydrogen carbonate (II), whose pyrolysis afforded N-dimethyl-3, 4-dibenzyloxyaniline (III), and the debenzylation of (III) with subsequent oxidation finally gave o-benzoquinone type compounds (VI) and (VII). (VI) was extremely sparingly soluble in water that its hemostatic activity was not examined.
On the other hand, methylation of 3, 4-dibenzyloxyaniline with formaldehyde and formic acid afforded needle crystals (XI) of m.p. 120-122°, which formed a monomethiodide and evolved formaldehyde on heating with acetic anhydride that (XI) was considered to be a kind of Tröger's base, discovered by Tröger. Its analytical values agreed well with those of the Tröger's base.