Nitro-, arylazo-, and amino-glyoxalines / by Robert George Fargher and Frank Lee Pyman.

  • Fargher, Robert George.
Date:
[1919?]
Catalogue details

Licence: In copyright

Credit: Nitro-, arylazo-, and amino-glyoxalines / by Robert George Fargher and Frank Lee Pyman. Source: Wellcome Collection.

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    Found, in substance dried at 110°, C = 34 6; H = 3'2; N = 24*6i C5H504N3 (171*1) requires C = 35T; H = 3*0; N = 24*6 per cent. It is soluble in aqueous alkalis, but not appreciably more soluble in dilute acids than in water. An aqueous solution, acidified with sulphuric acid, decolorises cold aqueous permanganate instantly. When treated with hydrochloric acid and sodium nitrite and poured into a solution of j8-naphthol in aqueous sodium hydroxide, it gives a reddish-brown colour. With sodium diazobenzene-_p- sulphonate in aqueous sodium carbonate, it gives a reddish-brown colour. It does not give any characteristic colour with sodium nitroprusside and sodium hydroxide. Action of Water at 170°.—After a preliminary experiment, in which it wTas found that the product contained ammonium carbonate, T33 grams of the acid and 30 c.c. of water were heated in a sealed tube for twelve hours at 170°, when a dark brown deposit formed. After adding alkali and distilling into standard acid, 0*157 gram of ammonia was found, whereas 0*132 gram repre¬ sents the liberation of one molecular proportion. From the resi¬ due of the distillation, small quantities of a crystalline picrate were isolated, but in insufficient amount for characterisation. Action of Boiling Aniline.—0*9 Gram of the acid was boiled with 10 c.c. of aniline for six hours under a reflux condenser, in which a small quantity of ammonium carbonate collected. The product was distilled with steam to remove aniline, and left a pale brown, aqueous liquor containing some resinous matter. The liquor was cooled, filtered, and mixed with cold saturated aqueous picric acid, when 1*0 gram of a crystalline picrate, melting at about 215°, was obtained. After crystallising this from water twice, it gave 0*4 gram of 2-aminoglyoxaline picrate, melting at 234° (corr.), the pure substance melting at 236°, and a mixture of the two at 234° in the same bath. From the picrate, the hydro¬ chloride and stannichloride were prepared, and identified as the salts of 2-aminoglyoxaline previously described. & The Wellcome Chemical Research Laboratories, London, E.C.h [Received, February 1th, 1919.]