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



The compound of m.p. 264°-265° on analysis 



2026 grm. gave 14'3 c.c. moist N at 14° and 725 mm. N = 8'37 per 

 cent. 



01960 grm. gave 137 c.c. moist N at 16° and 753 mm. 1ST = 8-24 per 



cent. Calculated for C^H^IS^ ; N = 8-4 per cent. 



The compound has therefore the formula : 



C r ,H 5 /\ 

 I 



c 



CH 3 1 ^ 



It was converted into the methosulphate by dissolving in eight times the 

 weight of nitrobenzene at 130° and adding half the weight of methylsulphate. 

 The crystalline product was filtered and washed with ether. 



[62. 63.] 2.Dimethylaminonaphthacridine and mMho chloride. — 



CH | | 



(CH 3 ) 2 N X/X/X/ 



It was prepared by the method of Ullmann and Marie,* by fusing tetra- 

 methyldiaminodiphenyl methane with /3-naphthol at 110°-120°, and raising the 

 temperature gradually to 180°-200°. The product was extracted with warm 

 alcohol which dissolves the naphthacridine compound, but leaves the hydra- 

 cridine. The hydracridine compound was suspended in boiling alcohol, 

 acidified with a few drops of hydrochloric acid and ferric chloride added until 

 the precipitation of the naphthacridine hydrochloride was complete. The 

 precipitate was filtered, dissolved in water, and re-precipitated with cone, 

 hydrochloric acid. It was filtered and dried in vacuo over caustic soda. The 

 base was precipitated from the dissolved hydrochloride with ammonia, and 

 after re-crystallisation from benzene melted at 185°. It was dissolved in 

 boiling xylene and the calculated amount of methyl sulphate added. The 

 precipitated methosulphate was washed with ether and dried ; on dissolving 

 it in water and adding sodium chloride solution the methochloride was 

 precipitated, filtered, and dried. To remove the sodium chloride the metho- 

 chloride was dissolved in alcohol, filtered, and evaporated to dryness. The 

 naphthacridine base was obtained from the first alcoholic filtrate by adding a 



* ' Ber.,' vol. 34, p. 4318 (1901). 



