ON A NEW a, 8 DIHYDROQUINOXALINE 



By John B. Ekeley 



The author, in conjunction with R. J. Wells/ has shown that, when 

 orthophenylenediamine reacts with acetone or with mesityloxide in 

 the presence of dry hydrochloric acid gas, a condensation takes place 

 with the formation of a new dihydroquinoxaline. The substance 

 was interesting in that it was the first member to be isolated of a theo- 

 retically possible series of dihydroquinoxalines having two imido groups. 

 It therefore ought to be possible to produce other members of the series 

 by using other diamines. Numerous trials with orthotoluylenedia- 

 mine (1:3:4) and with para-ethoxy-orthophenylenediamine have been 

 barren of results, and from these no base up to the present has been 

 isolated. In the case of orthoxylylenediamine (1:3:4:5), however, 

 the reaction takes place with almost the same ease as in the case of 

 orthophenylenediamine, and the base formed shows similar proper- 

 ties. It is a di-acid base, yields characteristic salts, and without doubt 

 is another member of the series. 



Ten grams of orthoxylylenediamine^ were dissolved in an excess 

 of mesityloxide, cooled, and a stream of dry hydrochloric acid gas 

 passed through the solution. In a short time the hydrochloric acid 

 salt of the base was precipitated. This was pressed out on a porous 

 plate, dissolved in water, filtered, and treated with a strong solution 

 of potassium hydroxide. The straw-colored precipitate of the new 

 base was filtered off, pressed out on a porous plate, and recrystallized 

 from dilute acetone. It yields straw-colored needles, extremely soluble 

 in most organic solvents and in acids. Melting point, 82°-83°. 



CARBON AND HYDROGEN DETERMINATION 



.2931 grm. substance yielded .8356 grm. CO3 and .2475 grm. HjO. 

 Ci^H.oN, , C = 77 . 75% Found, 77 . 77% Calc. 

 H= 9.41 " 9.26 



' This journal. Vol. II, No. 2, p. 123, and Berichte der Deulchen Chem. Ges., 38, 2259. 

 ' The diamine may be obtained with a splendid yield by the reduction of orthonitrometaxylidine with 

 2anc dust and sodium hydroxide by the method of Hiasberg. 



139 



