190 M. Otto on Benzoic and Hippuric Acids. 



the next higher homologous alcohol. Thus the conversion of 

 cyanide of ethyle into propylamine is expressed as follows : — 



€ 3 H 5 N + 4H =G 3 H 9 N or €3 ^1-N. 



The general method was as follows :■ — A large three-necked 

 AYoulfe, provided with a funnel tube and a gas- delivery tube, was 

 about three-fourths filled with granulated zinc ; water added, as 

 well as sulphuric acid mixed with the nitrile. The liquid poured 

 off from the mixture was distilled, and the distillate, which con- 

 tained much undecomposed nitrile, again acted on by acid and 

 zinc. From the solution of sulphate of zinc by far the greater 

 part was separated by crystallization, and nearly all the rest was 

 precipitated by alcohol. The last traces of zinc were separated 

 by means of sulphuretted hydrogen, after adding acetate of soda. 

 The filtrate from the sulphide of zinc was decomposed by caustic 

 soda, and the base which distilled over collected in hydrochloric 

 acid, and thus converted into the hydrochlorate. 



By this method, slightly modified in certain cases, Mendius 

 transformed hydrocyanic acid, G H N, into methylamine, G H 5 N ; 

 cyanide of methyle or acetonitrile, € 2 H 3 N, into ethylamine, 

 € 2 H 7 N; cyanide of butyle or butyronitrile, € 5 H 7 N, into amyl- 

 amine, C 5 H n N. He also effected the transformation of benzoni- 

 trile, G 7 H 5 N, into a new base of the composition G 7 H 9 N. 



Otto has investigated* some of the derivatives of benzoic and 

 hippuric acids. When hippuric acid is mixed with hydrochloric 

 acid and chlorate of potash added, products are obtained the 

 quantity of chlorine in which depends partly on the quantity of 

 chlorate of potash, and partly on the temperature of the opera- 

 tion. The product of the reaction is an oily liquid consisting 

 of bichlor- and monochlor-hippuric acid, which are easily sepa- 

 rated by recrystallization from hot water, the latter being much 

 the more soluble body. 



Mono chlor hippuric acid, G 9 H 8 CI NO 3 , is a viscous yellowish 

 mass, which reddens blue litmus ; insoluble in cold, it is soluble 

 in boiling water, and the solution on cooling becomes milky. 

 The salts of the alkalies do not crystallize ; the silver, lead, and 

 calcium salts crystallize well. 



Bichlorhippuric acid, G 9 H 7 CI 2 NO 3 , can be obtained in a soft 

 granular crystalline mass when allowed to stand for some time 

 under water. The potassium, sodium, calcium, barium, silver, 

 and lead salts all crystallize. 



The ether is obtained by dissolving bichlorhippuric acid in 

 absolute alcohol, saturating with hydrochloric acid, and digest - 



* Liebig's Annalen, May 1862. 



