Antiseptic Action and Chemical Constitution. 



345 



m- 



P- 



a- 



o- Acetyl aminoquinoline 



103° 

 161° 

 138° 

 178° 



By boiling each of the above with a little cone, hydrochloric acid and 

 concentrating the solution, the pure hydrochlorides crystallised with a brown 

 or yellow colour and were filtered and washed with alcohol. 



The hydrochloride of the ra-compound dissolves in water or alcohol with a 

 bright green fluorescence. All the hydrochlorides combine with potassium 

 cyanate and form orange, crystalline carbamido derivatives. 



The methochlorides were obtained from each of the acetyl derivatives by 

 dissolving the substance in three to four times its weight of freshly distilled 

 nitrobenzene and heating the solution to 150°. Kather more than the calculated 

 quantity of dimethyl sulphate was then added and after a minute the mixture 

 was removed from the bath. A portion of the methosulphate crystallised and 

 the remainder was precipitated by adding ether. After standing for a time 

 the nitrobenzene was removed as far as possible by washing with ether by 

 decantation and then evaporating the ether by a current of air. A few cubic 

 centimetres of cone, hydrochloric acid were added and the mixture boiled for 

 \ hour. The solution was concentrated on the water-bath. The o- and a- 

 compounds separated on cooling in brown crystalline crusts, the m- and ^-com- 

 pounds were crystallised from the hydrochloric acid solution by the addition 

 of alcohol and separated in bright yellow needles. The methochloride of the 

 meta-compound dissolves in water with a green fluorescence like the hydro- 

 chloride. The other three hydrochlorides and methochlorides exhibit no 

 fluorescence. 



[14.13] S.Hydroxyquinoline methopicrate and methochloride. — These sub- 

 stances were prepared from the sulphate of the base (Chinosol) as follows : — 



The base was separated from a solution of the sulphate by adding ammonia, 

 filtering and washing with water. It was then dried and heated for an hour 

 with one part of fused sodium acetate and four parts of acetic anhydride. 

 On adding water and a little ammonia until alkaline, the acetyl derivative 

 crystallised in long colourless needles, m.p. 75-7° after recrystallisation from 

 dilute alcohol. The substance was then dissolved in a little toluene and an 

 equal weight of methyl sulphate and boiled for an hour when the yellow 

 crystalline methosulphate separated. The toluene was decanted and the dry 

 residue boiled with cone, hydrochloric acid. In this way a reddish solution 

 was obtained from which the methochloride did not crystallise nor was the 

 base precipitated by ammonia. One portion was, therefore, evaporated to 

 dryness and formed a greenish-yellow solid which is very soluble in water and 



