Studies on Adrenochrome Derivatives. VI. Solubilization of Adrenochrome Monosemicarbazone and its Derivatives. (2).Synthesis and Structure of Sodium 1-Methyl-5-semicarbazono-6-oxo-2, 3, 5, 6-tetrahydroindole 3-Sulfonate

Abstract

In order to obtain water-soluble compound of adrenochrome monosemicarbazone (XI), reaction of (XI) and sodium hydrogen sulfite was carried out and a compound fairly well soluble in water was obtained. Its solubility is 15 mg./cc. at 0°, being about 50 times that of (XI). Detailed examinations of this substance indicated it to be sodium 1-methyl-5-semicarbazono-6-oxo-2, 3, 5, 6-tetrahydroindole 3-sulfonate (III). (III) converts to 1-methyl-5-semicarbazono-6-oxo-2, 3, 5, 6-tetrahydroindole 3-sulfonic acid (IV) and forms metal salts with barium, copper, silver, and other metals. Catalytic reduction of (III) affords 1 -methyl-5-semicarbazido-6-hydroxyindole (XII). 1-Methyl-4-hydroxy-6-semicarbazono-7-oxo-1, 2, 3, 4, 6, 7-hexahydroquinoline also reacted with sodium hydrogen sulfite to form water-soluble sodium 1-methyl-6-semicarbazono-7-oxo-1, 2, -3, 4, 6, 7-hexahydroquinoline 4-sulfonate (X).