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.

    38/44 (page 254)
    with A, and gave 4*7 grams of aniline, together with 3-8 grams of a brown, gummy, hydrochloride. This was a mixture from which only very small quantities of crystalline compounds were isolated by various methods of treatment. The hydrochloride, C9H]0ON2,HC1, crystallises from water in colourless, transparent, rectangular tablets, which melt and effervesce at 308° (corr.) after sintering and darkening earlier. It is readily soluble in hot, less so in cold water, giving a solution which is strongly acid to litmus. Found, in air-dried salt, loss at 110° = 1*7. Found, in salt dried at 110°: 0 = 54*8, 54*8, 55*0; II = 5*9, 5*0, 5*2; N = 13*5 ; 01 = 17*2. C9H10ON2,HC1 (198-6) requires 0 = 54*4; H = 5*6; N = 14’l; Cl = 17*8 per cent. The corresponding base is obtained by adding ammonia to a con¬ centrated aqueous solution of' the hydrochloride. It crystallises from water in brilliant, elongated prisms, which are anhydrous and melt at 185° (corr.). Found: C=66*6, 66-1 ; H = 6*2, 6*1; K=17*8, 17*2. C9H]0ON2 (162*1) requires C = 66'6; H = 6*2; N = 17*3 per cent. The base is more readily soluble in dilute aqueous sodium hydr¬ oxide than in water. With silver nitrate it yields a white pre¬ cipitate, which dissolves on the addition of ammonia; on boiling this solution, no reduction fakes place. The base does not reduce Fehling’s solution on boiling. It is stable towards cold aqueous acid potassium permanganate, but slowly reduces cold alkaline permanganate, giving a green solution. It gives no coloration with sodium diazobenzene-p- sulphonate in aqueous sodium carbonate. When dissolved in hydrochloric acid and mixed with sodium nitrite, it fails to couple with /3-naphthol in aqueous sodium hydroxide. The hydrochloride is recovered slightly charred, but otherwise unchanged, after the action of concentrated hydrochloric acid at 170° for two and a-half hours. The quantity of this compound available was insufficient for the determination of its constitution, and we are consequently unable to offer any suggestion as to how one of the carbon atoms of the starting material has been eliminated. It is perhaps worth record¬ ing that the formula C9H10ON2 is that of a phenyldihydro- glyoxalone.