19151 Isomerism of the Hydeojuglons 193 



semicarbazone of i^-hydkojuglone 

 CioHgO.: K NH. CO. NHg 



Warm alcoholic solutions of y8-liydrojiiglone (3g in 65cc) 

 and of semicarbazine (1.5g in 35cc) are mixed and a bottle is 

 filled to the stopper with the solution and closed. After four 

 days dark yellow hard globular crystals, weighing 3.8g, have 

 crystallized out. They are washed with alcohol and recrystal- 

 lized from much boiling benzene. Only one half of the product 

 could be brought into solution, an insoluble amorphous substance 

 remaining behind. The semicarbazone forms beautiful feather 

 like groups of needles or sharply truncated prisms of pale yel- 

 low color which melt at 197-8° with decomposition. The com- 

 pound is easily soluble in hot acetic acid, difficulty soluble in 

 alcohol and in benzene, insoluble in ether and in ligroin. 



0.1460g Substance gave 0.3062g COo and 0.0650g H.O 

 0.1307g Substance gave 21.4cc N" at 18° and 7l3mm 

 Calculated for CnHjiOgls's: C, 56.65; H, 4.72; N, 18.03 

 Found ^ C, 57.19; H, 4.98; E", 17.86 



PHENYLSEMICARBAZONE OF j8-HYDROJUGLONE 



CioHgO.: K NH. CO. NHCgHs 



We mixed cold saturated solutions of ^-hydrojuglone (Ig) 

 and phenylsemicarbazine (l.lg) in absolute alcohol. The re- 

 action product began to separate within a half an hour and 

 the separation was complete in 24 hours. The phenylsemicar- 

 bazone formed a pulpy mass of bright yellow needles in star 

 shaped groups. The yield amounted to 1.7g. By recrystalli- 

 zation from considerable boiling acetone (350cc required by 

 Ig) or from xylene long thin needles were obtained which car- 

 bonized at 243° without melting. 



0.1687g Substance gave 0.4090g Coo and 0.0744g HoO 

 0.1046g 12.9cc N, dry, at 25° and 721mm 



Calculated for C17H15O3N3: C, 66.03; H, 4.85; ^, 13.59 



C, 66.12; H, 4.90; N", 13.40 



The phenylsemicarbazone is insoluble in ether, in alcohol 



