Antiseptic Action and Chemical Constitution. 349 



for 5 minutes. The cold fused mass was extracted with alcohol, poured into 

 water, and the colourless precipitate filtered. The yield is nearly theoretical, 

 and the product melted at 157°. 



II I I I 



y\/ \/\/ 



Diamino dinaphthyl. Dinaphfchylimine. 



\ 



Acridine Derivatives: [30] Acridine Methochloride. — Acridine base was 

 precipitated from pure acridine hydrochloride by the addition of ammonia, 

 filtered and dried : 1*5 grms. was dissolved in 7 grms. of nitrobenzene, heated to 

 150°, and 1*7 grms. of methyl sulphate added, and, after 1 minute, cooled. 

 Yellow prisms of the methosulphate separated and were filtered and washed 

 free from nitrobenzene with ether. The methosulphate is soluble in water, 

 and from the solution the methoxide was precipitated with ammonia and 

 crystallised from alcohol in which it is much less soluble than acridine. It 

 crystallises in colourless plates, m.p. 140°. It dissolves readily in hydro- 

 chloric acid and the methochloride crystallises on concentration. It may be 

 re-crystallised from alcohol and ether. It is very soluble in water, to which 

 it imparts a green fluorescence. 



[32.] 9-Phenylacridine methochloride.- — 9-Phenylacridine was prepared by 

 the method of Bernthsen*. 50 grms. of benzoic acid and 70 grms. of diphenyl- 

 amine gave 35 grms. of phenylacridine, m.p. 183°. To convert it into the 

 methochloride the above method was adopted. The methosulphate does not 

 separate on cooling, but on adding ether a brown oil was precipitated, which 

 soon solidified. The ether solution was decanted and the methosulphate 

 washed with ether. Concentrated hydrochloric acid was then added and the 

 mixture boiled gently for a short time, when, on cooling, the methochloride 

 separated in green leaflets, which readily dissolve in water with a yellow 

 colour. 



[33.] S.Q.Dimethylacridine was prepared according to Ullmann's method.f 

 It crystallises from dilute alcohol in yellow needles, m.p. 171°, which fluoresce 

 in solution with a blue colour. 



The action of ethyl iodide on acriflavine in ethyl alcohol was examined with 

 the object of obtaining the tetraethyl derivative. The mixture heated to 

 100° for 6 hours in a sealed tube gave a red crystalline product, which 

 appeared to be a periodide. Its antiseptic action was inferior to that of 

 acriflavine and it was not further investigated. It is recorded in the Table as 

 acriflavine +C2H5I. 



* ' Annalen,' vol. 224, p. 13 (1884). 

 + 'Ber.,' vol. 36, p. 1017 (1903). 



