30 PROCEEDINGS OF THE AMERICAN ACADEMY. 



Action of Aniline. 



If aniline is added to a solution of the a-bronicrotonolactone in 

 dilute alcohol, the bromine is gradually displaced at ordinary tempera- 

 tures, and the corresponding phenylamidocrotonolactone is formed. 

 The somewhat dark-colored crystalline mass, which separates after 

 the lapse of twenty-four hours, may be purified by recrystallization 

 from glacial acetic acid, and afterward from alcohol. The a-chlor- 

 lactone which was described by Hill and L. L. Jackson,* and of 

 which we shall speak later, also reacts as readily with aniline, and 

 naturally gives the same product. The same body may furthermore 

 be made, although with more difficulty, by the reduction of the 

 a-phenylarnido-/3-bromcrotonolactone. The elimination of the bromine 

 takes place so slowly in acid solution that we have found it more ad- 

 vantageous to employ sodium amalgam with dilute alcohol, and to 

 allow the reduction to proceed in alkaline solution at ordinary temper- 

 atures. Although more or less decomposition of the phenylamido- 

 bromcrotonolactone takes place, as the strong odor of phenylisocyanide 

 which is developed shows, a satisfactory product is obtained in this 

 way. The finely powdered a-phenylamido-/3-bromcrotonolactone is 

 suspended in 50 times its weight of about GO per cent alcohol, and an 

 excess of sodium amalgam containing 2 per cent of metallic sodium is 

 added. The substituted lactone gradually goes into solution, and we 

 usually have found the reduction complete at the end of four or five 

 hours. The clear solution is then acidified with acetic acid, the alco- 

 hol driven off upon the water bath, and the crystalline product which 

 separates recrystallized from glacial acetic acid. Occasionally we 

 have found it necessary to treat the product a second time with sodium 

 amalgam in order to remove the last traces of bromine. 



I. 0.1991 grm. substance gave 0.4996 grm. C0 2 and 0.09G2 grm. 

 H„0. 

 II. 0.2114 grm. substance gave 14.9 c.c. of moist nitrogen at 21°. 3 

 and under a pressure of 754 mm. 



* These Proceedings, XXIV. 353. 



