Antiseptic Action and Chemical Constitution. 353 



colour. It was filtered and cooled. The methochloride separates in brown, 

 glistening plates, which dissolve in water but are less soluble in dilute hydro- 

 chloric acid. It dissolves in alcohol with green fluorescence. 



[67.] 2.7 '.Dihydroxy-3. 6. dimethyl acridine. — The compound was obtained 

 from tetramethyl diamino ditolylmethane, by the method of Ullmann and 

 Fitzenkam* 



It was converted into the diacetyl derivative by boiling with acetic anhydride 

 and fused sodium acetate. 



[68.] 2.7. Dihydroxy-3. 6. dimethyl acridine methochloride. — The acetyl deriva- 

 tive was dissolved in toluene and to the solution an excess of methyl sulphate 

 was added and the mixture boiled. On standing, orange needles separated and 

 were filtered and washed with toluene. On heating the substance with cone, 

 hydrochloric acid on the water-bath, it first dissolved and then suddenly 

 formed a pasty mass of clusters of lemon yellow needles of the methochloride. 

 The crystals were filtered and washed with cold water and then with alcohol. 

 In the latter it dissolves slightly with green fluorescence. It dissolves to 

 some extent also in hot water with a yellow colour, and is readily soluble in 

 ammonia and sodium hydroxide solutions. 



[50.] 2 .7 '.Diamino- -3.6. dimethyl-9. phenyl acridine (Benzoflavine) was prepared 

 according to the method of Meyer and Gross.f It was purified by pre- 

 cipitating the base with ammonia, dissolving the filtered, washed and well- 

 pressed base in glacial acetic acid, adding cone, hydrochloric acid and diluting 

 until a permanent turbidity was formed. The hydrochloride separates in red 

 crystals. 



[51.] 2.7. Diamino-3.6.dimethyl.9-phenyl acridine methochloride was obtained 

 by the method employed in the case of acridine yellow by heating the dry 

 base with acetic anhydride and methylating the acetyl derivative with methyl 

 sulphate. On hydrolysis of the methosulphate with hydrochloric acid the 

 methochloride separates in bright red needles. In the absence of hydro- 

 chloric acid, it dissolves in water and on cooling gelatinises. 



[52.] 2.7. Tetramethyl diamino-acridine (Acridine orange) was obtained by 

 the method of BehringerJ and Ullmann and Marie. § Tetramethyl-diamino 



CH 



* ' Ber.,' vol. 38, p. 3787 (1905). 

 t ' Ber.,' vol. 32, p. 2356 (1899). 



} ' J. prakt. Chem.,' vol. 54, p. 240 (1896). 

 § ' Ber.,' vol. 34, p. 4307 (1901). 



VOL. XCIIL- 



•B. 



2 c 



