Adrenochrome monosemicarbazone is sparingly soluble in water (0.3 mg./cc. at 0°), that there is some difficulty in preparing highly concentrated solutions. Urea is generally used as the solubilization agent but this substance was found to be ineffective in this case. β-Hydroxyethylurea, introduced with the soluble hydroxyethyl group, was also ineffective. However, adrenochrome 4-β-hydroxyethylsemicarbazone was found to be 3.5 times more soluble than the ordinary monosemicarbazone. 4-β-Hydroxyethylsemicarbazones were prepared of three compounds of 5, 6-dioxo-2, 3, 5, 6-tetrahydroindole type
5α) and two compounds of 6, 7-dioxo-1, 2, 3, 4, 6, 7-hexahydroquinoline type
1) and they were all found to be far more easily soluble than the monosemicarbazones. 4-β-Hydroxyethylsemicarbazide was prepared by heating acetone semicarbazone and monoethanolamine at 180° to form acetone 4-β-hydroxyethylsemicarbazone and its hydrolysis with mineral acid.
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