Antiseptic Action and Chemical Constitution. 355 



saturated solution of potassium nitrate, the methonitrate crystallised on 

 standing in red needles. They were filtered, washed with a little water, and 

 dried. On grinding; with ammonia solution the methoxide was obtained as a 

 sticky red mass with green iridescence which dissolves in hydrochloric acid 

 forming the methochloride as a hygroscopic mass which could not be prepared 

 in the crystalline state. 



[58.] 2. Amino - S.methylnaphthacridine was prepared according to the 

 directions of Ullmann and Naef.* The base, after re-crystallisation from 

 xylene, melts at 244°. It was acetylated, as described, and the acetyl 

 derivative melted at 320°-321°. 



[59.] I.Amino - 3.methylnaj)hthacridine methochloride. — - 6 grm. of the 

 acetyl derivative was dissolved in 2 c.c. of nitrobenzene heated to 160°, and 

 0'3 grm. of dimethyl sulphate added when the mixture crystallised to a semi- 

 solid mass, which was filtered and washed with ether. The product, after 

 boiling with cone, hydrochloric acid, became dark red, and on concentrating 

 the solution on the water-bath and cooling the methochloride crystallised in 

 long; red needles. 



CH 



N 



CH 3 CI 



[60.] 2. Amino - S.methyl - 9 .phenylnaphthacridine. — The substance was 

 prepared by adding 5 grms. of tetramino-ditolylphenyl methane (Meyer and 

 Gross),f to 8 grms. of /3-naphthol at 150° and heating for an hour to 180°-200°- 

 The sticky product was dissolved in 10 c.c. of glacial acetic acid, diluted with 

 an equal volume of water, and poured into 10 grm. of caustic soda in 50 c.c. 

 of water. The yellow precipitate was filtered and washed with dilute caustic 

 soda solution and hot water to remove the naphthol, and the product 

 crystallised from alcohol. The undissolved portion was filtered off. It 

 crystallises from nitrobenzene and also from benzene in yellowish brown 

 needles, m.p. 264°-265°. The alcoholic nitrate was heated to boiling, water 

 added till turbid, and allowed to cool. The crystalline product was re- 

 crystallised from benzene from which it separates in yellow needles, m.p. 

 269°-27l° 



* ' Ber.,' vol. 33, pp. 915, 2473 (1900). 

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



2 C 2 



