146 



OXYPHEXYLISOAMYLURETHANE. 



0-aminophonol was prepared by the reduction of the nitrophenol. Two 

 grams of this were suspended in ether and the calcuhited amount (2 mol.) of 

 chlorcarbonicisoamj'lether slowly added. The hydrochloride of one molecule 

 of the aminophenol precipitated. After filtering, the ether solution was 

 evaporated, leaving about two grams of a solid. It crystallized from ligroin 

 in white needles melting at 68.5°-69.o°. It is insoluble in cold water and 

 acids, but is sparingly soluble in hot water and very soluble in cliloroforni, 

 benzol, alcohol and ether. It is also quite soluble in dilute alkalis and from 

 this solution is precipitated by acids thus showing its acid character. 



The same substance was also produced l)y the reduction, with tin and 

 acids, of o-nitroi)henylisoamylcarbonate made by Ransom's method (loc. 

 cit.). The melting point was the same, and a mixture of the two had the 

 same melting point as either. 



Another sample of the nitroisoamylcarbonate was reduced, but as soon 

 as the action was complete the product was thrown into a concentrated (1:1) 

 sohition of potassium hydroxide kept cold in a freezing mixture. This solu- 

 tion was cpiickly extracted with ether and the ether solution dried with solid 

 potassium hydroxide. When dry the ether solution was saturated with dry 

 hj'drochloric acid gas. A voluminous white |)iccipitate separated wliicli was 

 filtered out and Cjuickly dried on a porous plate in a desiccator. The melting 

 point was 133°-134° and the substance was cpiite soluble in cold water and 

 acids, but alkalis precipitated an oil from the mixture. A small amount of 

 this was dissolved in warm water and allowed to stand. Soon an oil sei)arated 

 which was extracted with ether. On evaporating the ether a solid remained 

 which was soluble in alkalis and h:id all tlie jjroperties of the urethane de- 

 scribed above. Kvidently the .substance melting at 133'^ was the liydrochlor- 

 ide of o-aminophenylisoamylcarbonate wliich changed to the >n-ethane on 

 being warmed with water. In the dry condition tlic liydrocliloride is 

 moderately stable. 



BENZOYL 0-OXYPHENYUSO.\.MYLXUETHAXE. 



One and five-tenths grams of the oxv-phenylisoamylurethane were dis- 

 solved in a slight excess of a 10 per cent, solution of potassium hydroxide, 

 and to this was added 0.8 grams (one mol.) of benzoyl chloride. Slowly a 

 brown oil sejjarated which solidified in an ice box. .\fter extracting with 

 ether and recrystallizing several times from dilute alcohol wliite needle shai)e(l 



