154 PROCEEDINGS OF THE AMERICAN ACADEMY. 



I. 0.1089 gram of the substance gave by combustion 0.2085 gram of 

 carbonic dioxide and 0.0715 gram of water. 



II. 0.1147 gram of the substance gave by the method of Carius 0.0931 

 gram of argentic chloride. 



III. 0.1216 gram of the substance gave 0.09G9 gram of argentic 

 chloride. 



Calculated for Found. 



C6CI2C5II11NHONH3C5H11O2. I. n. III. 



Carbon 52.60 52.22 



Hydrogen 7.19 7.29 



Chlorine 19.45 20.06 19.71 



These results show that the substance is the isoamylamine salt of the 

 dichlorisoamylamidoxyquinone. The formation of such a body from the 

 oxide can be explained by the following reactions.* In the first place, 

 the addition of one molecule of isoamylamine to the atom of oxygen 

 forming CGCl20CH30H(C5HiiNH)(OCOCeH5).30CH3 ; next, the re- 

 placement of the methoxy group by an isoamylamido group, and the 

 addition of a molecule of isoamylamine to the hydroxyl giving a complex 

 substance, which must have had this formula : — 



C6Cl2(C5HnNH)(OHNH2C5Hn)C5HnNH(OCOC6H5)20CH3. 

 This would finally be decomposed by the removal of beuzisoamyla- 

 mide and benzoic methylester leaving the body analyzed 



CeCLCsHnNHOHCsHiiNHoOs. 

 That the methoxy group can be replaced by the isoamylamido radi- 

 cal and the substituted acetal sajDonified to the quinone under these 

 conditions will be proved by some experiments described later in this 

 paper. 



Properties of the Isoamylamine Salt of Dichlorisoamylamidoxyquinone, 

 C6Cl2(C5HnNH)(ONH2C5Hn)02. — This substance, when crystallized 

 from a mixture of benzol and methyl alcohol, appears in purplish 

 red needles, which, when examined with the microscope, are seen to 

 be long, very slender spindle-shaped plates or flattened needles of a 

 pale purple color. When heated it decomposes into the free phenol 

 melting at its usual temperature, 188°, and isoamylamine, which could 

 be seen coating the upper parts of the melting tube, and was recog- 



* These reactions are arranged in the order which we think will be most easily 

 understood. We do not mean to imply that they took place in this order ; in fact, 

 our work on the yellow product seems to indicate that they did not. 



