r 105 



'-V^' 



^,;ij\,i.«Un InatfJuf/J 



MAR" 5 1921 



IX. 



SOME PEEIVATIVES OF NITEOTOLUIDINE 



(4-nitro-2-amiclo-l-methyl-benzene). ^ " """ —■ -"- 



By a. G. G. LEOKAED, A.R.C.Sc.I., B.Sc, Ph.D. ; 



AND 



AGNES BllOWNE, A.R.C.Sc.I., B.Sc. 



Keail Ju.vK 'i-J. Puljlislied Augl'.st 10, 1920. 



The nitTO-oi-tho-toluidine CsH;, (NHo) Me (NO,) [NH, : Me : NOj -1:2:5] 

 used for the following preparations wa.s obtained by nitration of o-toluidine 

 in excess of sulphuric acid (N51ting and Stoecklin, Ber. 24, 566). Three lots 

 of 100 grams of the base gave an average yield of 83 grams of nitro-toluidine, 

 m. pt. 107" C. 



Nitro-methyl-phenyla-M-^-Naphthol, CeHaMe . NO, . N, . CioHe OH 



(2.) (5.) (1,1.) (2.) 



5 grams nitro-ortho-toluidine were dissolved in 75 c.e. warm sulphuric acid 

 ( 10'/,), and the solution rapidly cooled to 0" C, whereby the sulphate was 

 precipitated in a fine state of division. A cold solution of 2-27 gram sodium 

 nitrate was added slowly, the diazo solution quickly filtered and added with 

 constant stirring to a cold solution of 474 grams of /3-naphthol in 500 c.c. 

 of a o^/o solution of sodium hydroxide. During the mixing of the liquids a 

 bright red precipitate separated. Stirring was continued for an hour, when 

 the whole was heated to 80° C. on the water bath, cooled, filtered, and the 

 precipitate washed with water. Yield, 9*5 grams. 



The product 'thus obtained was bright red, and melted with decomposition 

 at 204° G. It is insoluble in water, hydrochloric acid, and sodium hydroxide ; 

 it dissolves in benzene, ether, and alcohol, and crystallizes from its solution 

 in alcohol in long red needles. 



When applied to the fibre in the same way as p-nitrauiline red, it dyes 

 cotton a deep orange colour. 



Analysis :• — 



(1) '2997 gram gave 3o-6 c.c. moist nitrogen at 17° C. and 785 mm. 



7 N = 13-42. 



/o 



(2) '3008 gram gave 34"4 c.c. moist nitrogen at 18° C. and 765 mm. 



%N = 1:3-30. ■ 



CnH.sOsFs-requiTes I3'-€8. 



BCTENT. PROC. li.D.S,, VOL. XVI., .Mi. IX. N 



