214 PROCEEDINGS OF THE AMERICAN ACADEMY 



XIV. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY 

 OF HARVARD COLLEGE. 



ON CERTAIN DERIVATIVES OF PYROMUCAMIDE. 



By Charles E. Saunders. 



Presented by Henry B. Hill, November 9, 1892. 



This investigation was undertaken at the suggestion of Professor 

 H. B. Hill, in the hope of obtaining from pyromucamide or its deriv- 

 atives, through Hofmann's * reaction, an amine having the nitrogen 

 atom directly united to a carbon atom of the furfuran ring, no such 

 amine being at present known. Since preliminary experiments 

 with pyromucamide had shown that the reaction was complicated 

 by products formed through the action of the bromine upon the 

 furfuran group, 08-dibrompyromucamide was chosen as better 

 adapted to the purpose, since the corresponding acid is unaffected 

 by bromine. In this case, however, the product proved to be the 

 nitrile of the acid, instead of the amine, with one less carbon atom. 

 The behavior of pyromucamide with dry bromine was next studied, 

 and a stable tetrabromide isolated, and at the same time the action 

 of bromine in aqueous solution upon pyromucamide was examined 

 in order to find an explanation of certain striking color reactions 

 which had previously been observed in this Laboratory. 



The Action of Bromine and Potassium Hydroxide on 

 /38-Dibro mpyromuca m ide . 



Bromine alone has no marked action on /3S-dibrompyromucamide, 

 the amide dissolving quietly in the bromine. On evaporating, the 

 amide can be recovered unchanged, though the removal of the last 

 portions of bromine at ordinary temperatures occupies considerable 

 time, indicating perhaps the production of an unstable tetrabro- 



* Berichte der deutsch. chera. Gesellsch., XIV 2725; XV. 407, 752, 762; 

 XVII. 1406, 1923 ; XVIII. 2734. 



