Some aspects of the Zimmermann reaction

Abstract

The structure of 3[beta]-hydroxy-17-oxoandrost-5-en-16[xi]-yl-2,4-dinitrobenzene was assigned to a yellow crystalline compound isolated by acidifying the reaction mixture obtained from denydroepiandrosterone, m-dinitroben-zene and alkali. The yellow compound was converted by alkali into a violet product formulated as its para-quinonoid aci-form. The yields of the quinonoid compound were determined in the analytical Zimmermann test carried out under different conditions. Replacement of alkali by quaternary-ammonium hydroxides gave rise to higher yields of the quinonoid compound and lower reagent blanks. The analytical test was accordingly modified and adapted to the accurate determination of 0.5 [mu]g. or more of 17-oxo steroids.