Antiseptic Action and Chemical Constitution. 



359 



and Mauther,* and converted into the acetyl derivative.! It was recrystal- 

 lised from nitrobenzene and forms a light brown micro-crystalline powder 

 which turns brown at 206° and melts about 270°. The latter was dissolved 

 in ten times its weight of nitrobenzene at 150°, and 1 mol. of methyl 

 sulphate added. The methosulphate, which was precipitated, was washed with 

 ether and the product boiled with cone, hydrochloric acid and evaporated on 

 the water-bath. The methochloride crystallised in black needles which were 

 filtered and dried. 



[76.] 2.Dimethylamino-7.aminophenazine methochloride. — The compound 

 was prepared according to the method described by Karrer,j from a 

 mixture of para- and meta-dimethyl phenylene diamine by oxidation 

 with potassium dichromate. The phenazine salt was precipitated by zinc 

 and sodium chloride and the base separated from the solution in hydro- 

 chloric acid by sodium hydroxide. It was purified by redissolving in acetic 

 acid and precipitating with ammonia. It forms a blue-black powder slightly 

 soluble in alcohol with a deep violet colour, and readily soluble in dilute 

 acids giving a violet solution and forming the hydrochloride 



N 



(ch 3 ) 5 n! x/ ! V/ Mnh 2 -hoi. 



N 



/\ 



CH 3 CI 



[77.] 2.Dimethylamino-7.amino-6.methylphenazine hydrochloride (Tohtylene 

 red). — The substance was obtained by following the directions of Witt.§ It 

 was purified by crystallisation from alcohol. The base was obtained by 

 precipitation with sodium hydroxide, and was washed, dried and acetylated in 

 the usual way. The acetyl derivative crystallises in brown plates. The 

 rnethiodide was obtained in microscopic black crystals which dissolve in water 

 and alcohol with a deep violet colour, by heating the acetyl derivative with 

 methyl iodide in a sealed tube for several hours to 100°. 



[84.] 2.Dimethylamino-7-amino-§.methylphenazine methochloride. — The 

 above acetyl derivative was dissolved in five times its weight of nitrobenzene 

 heated to 160°, and rather more than the calculated weight of methyl sulphate 

 added. After a minute or two the mixture was cooled and the resulting 

 black precipitate washed with ether and dried. The product was then 

 hydrolysed with cone, hydrochloric acid, when the liquid became deep 



* ' Ber.,' vol. 35, p. 4302 (1902). 



t Fischer and Hepp, 4 Ber.,' vol. 22, p. 358 (1889). 



\ 'Ber.,' vol. 49, p. 1643 (1916) ; vol. 50, p. 420 (1917). 



§ ' Ber.,' vol. 12, p. 921 (1879). 



