DEGRADATION OF JERVINE TO tion was basified with ammonia and extracted with 250 cc. of ether in three successive portions. The washed ether solution deposited a sparingly soluble base while it was being evaporated. The colorless prisms, after washing with ether and then with methanol melted sharply at 246" in an evacuated tube. In an open tube this base, which is evidently 2,3dihydroxy-9,lO-demethoxy-6 -methyltetrahydroprotoberberine, melted with decomposition a t 200-210°.Anal. Calcd. for CzoH2304hT: N, 4.10. Found: N, 4.27.The crystalline base was dissolved in hot methanol (sparingly soluble) and the rapidly cooled solution treated with an ethereal solution of diazomethane. The brisk evolution of nitrogen ceased after several hours and the non-phenolic base, which was readily isolated from the reaction mixture, crystallized from methanol in the characteristic stout prisms of a!-corydaline. Either alone or in admixture with an authentic specimen it melted sharply a t 135".Oxidation of Thalictricavine.-A small amount of the base was dissolved in very dilute hydrochloric acid and the solution then treated with aqueous sodium carbonate until the turbidity was just permanent. An excess of aqueous potassium permanganate was added. After 5 to 6 hr. the excess reagent was destroyed with sulfur dioxide and the acidified mixture then extracted with ether. The residue from the ether extract was dissolved in a small volume of water, the solution filtered to remove a turbidity, treated with excess ethylamine, and evaporated to dryness. The residue thus obtained was sublimed in DUCUO and the crystalline sublimate washed with ether-hexane, and then recrystallized from dilute methanol. The colorless fine needles thus obtained melted at 168-169' either alone or in admixture with an authentic specimen (m.p. 170') of the Y-ethylimide of hydrastic acid.The degradation of jervine by means of acetic anhydride and zinc chloride to a nitrogen-free substance is described. Evi-The structure of jervine is discussed in dence is presented, on the basis of which structure I11 is assigned to this substance. the light of this and other available evidence and found to be most satisfactorily expressed by formula 11.
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