146 



OXYPHENYLISOAMYLURETHANE. 



( )-ainiii()i)lieiu)l was i)repared by the reduction of the nitroplieiiol. 'I'wo 

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

 chlorcarbonicisoamylether slowly added. The hydrochloride of one molecule 

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

 ev^aporated, leaving about two grams of a solid. It crystallized from ligroin 

 in white needles melting at 68.5°-69.5°. It is insoluble in cold water and 

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

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

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



The same substance was also produced by the reduction, with tin and 

 acids, of o-nitrophenylisoamylcarbonate 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) 

 solution of potassium hydro.xide kept cold in a freezing mixture. This solu- 

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

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

 hydrochloric acid gas. A voluminous white precipitate separated which was 

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

 point was 133°-134° and the substance was quite 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 separated 

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

 which was soluble in alkalis and had all the properties of the uicthanc de- 

 scribed above. Evidently the substance melting at 133° was the hydrochlor- 

 ide of o-aminophenylisoamylcarbonate which changed to the urethane on 

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

 moderately stabl(>. 



BENZOYL O-OXYPHENYLISO.VMYLURETHANE. 



One and five-tenths grams of the o\yph(>nylisoaniylurethane were dis- 

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

 and to this was added O.S grams (one mol.) of l)enzoyl chloride. Slowly a 

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

 ct hcc and rcci-yst alii zing scxci'al times from dihite alcoliol white needle sliajx'd 



