358 Mr. C. H. Browning and others. Relationships between 



Phenazine Derivatives. 



[69-71.] Phenazine was prepared by the method of Kehrmann and Havas* 

 by heating a mixture of o-amino- and o-nitro-diphenylamine with fused 

 sodium acetate. It melts at 170° — 171°. The methosulphate and metho- 

 chloride were obtained in the same manner as the corresponding acridine 

 compounds. The phenazine was dissolved in five times its weight of nitro- 

 benzene, heated to 120°, and freshly distilled methyl sulphate equal in weight 

 to the phenazine was added, the mixture stirred and kept for 5 minutes at 

 100°-110° and cooled. The methosulphate separates; ether was added to 

 complete the precipitation and the product filtered and washed. It forms 

 greenish yellow prisms. The methochloride was prepared by first separating 

 the base with ammonia and evaporating the red solution, taking up with 

 alcohol to remove ammonium sulphate and then evaporating to dryness. The 

 methochloride was prepared by dissolving the base in hydrochloric acid and 

 concentrating the solution. It forms greenish crystals. 



[72.] 2.Aminophcnazine was prepared by (A) the method described by 

 Wohl and Lange,f from o-nitraniline and aniline-hydrochloride in presence 

 of fused zinc chloride. The amino-phenazine was separated from the 

 product by sublimation and crystallises in brilliant red needles melting at 

 283°, which after crystallisation melt at 288°. The acetyl derivative was 

 obtained by heating for a short time with an equal weight of fused sodium 

 acetate, and twelve to fifteen times its weight of acetic anhydride. When 

 poured into water and neutralised with ammonia it formed a buff-coloured 

 crystalline powder. The dry acetyl derivative was dissolved in ten times its 

 weight of nitrobenzene heated to 120° and methyl sulphate, equal in weight 

 to the acetyl derivative, added and the mixture cooled slowly. Ether 

 precipitates the methosulphate, which was filtered and washed with ether. 

 It was then boiled with water to remove nitrobenzene and filtered. About 

 an equal volume of cone, hydrochloric acid was added and evaporated to 

 dryness. The methochloride, which is very soluble, was dissolved in alcohol, 

 filtered and evaporated. It forms a red, crystalline residue which dissolves 

 in water and alcohol with a bright magenta colour. 



(B) A second process for preparing aminophenazine is to pass dry 

 ammonia into an alcoholic solution of phenazine methyl sulphate according 

 to the method of Kehrmann and Havas.J The products in the two cases 

 appeared to be identical and to have identical bactericidal properties. 



[74.] 2.'i.Diaminophenazine was prepared by the method of Ullmann 



* 1 Ber.,' vol. 46, p. 341 (1913). 

 t 'Ber.,' vol. 43, p. 2186 (1910). 

 % 'Ber.,' vol. 46, p. 431 (1913). 



