The abnormal behaviour of glyoxaline-carboxlic esters and anilides towards diazonium salts / by Robert George Fargher and Frank Lee Pyman.

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

Licence: Public Domain Mark

Credit: The abnormal behaviour of glyoxaline-carboxlic esters and anilides towards diazonium salts / by Robert George Fargher and Frank Lee Pyman. Source: Wellcome Collection.

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    mineral acids, the corresponding methyl ester is insoluble even in excess (Frankel and Spiro, loc. cit.). Experimental. The esters described in this communication were prepared by boiling the acids with absolute alcohol saturated with hydrogen chloride. After removing the excess of alcohol and adding cold saturated aqueous potassium carbonate, the esters of the 2-alkyl- glyoxaline-4-carboxylic acids separated in a crystalline state. The other esters were extracted from the solutions by means of chloro¬ form, and crystallised either as base or as hydrogen oxalate. Ethyl 2-methylglyoxaline-^-carhoxylate crystallises from ethyl acetate in clusters of fine, shimmering needles, which melt at 156° (corr.) and are anhydrous. It is sparingly soluble in water, but readily so in alcohol or ethyl acetate. Found: C = 54*3; H = 6-7; N = 17*9. C7H10O2N2 (154T) requires C = 54'5; II = 6*5; N = 18'2 per cent. The ester gives no coloration with sodium diazobenzene- 7>-sulphonale in sodium carbonate solution. 2-Ethylylyoxaline A-carboxylic Acid and, its Derivatives. 2-Ethylylyoxaline-4:-carboxy anilide is prepared from 2-etliyl- glyoxaline-4:5-dicarboxylic acid in a yield amounting to 45 per cent, of the theoretical by the general method described in a previous communication (this vol., p. 217). It is readily soluble in alcohol but very sparingly so even in boiling water, from which it crystallises in clusters of fine needles; these are anhydrous and melt at 193° (corr.), sintering from 190°. It gives no coloration with sodium diazobenzene-p-sulphonate in sodium carbonate solution. Found: C = 66*6; H = 5-8; N = 19’2. CjoHjgONs (215-2) requires C = 66’9; H = 5'6; N = 19’5 per cent. 2-Ethyl(jlyoxahne-A-carboxylic acid is obtained in good yield by the hydrolysis of the corresponding anilide by dilute hydrochloric acid at 130°. It is readily soluble in hot water, but sparingly so in cold, and crystallises from the former in well-defined, pris¬ matic needles which contain two molecules of water of crystallisa¬ tion. After drying at 110°, it melts at 252° (corr.), sintering from 248°. It gives an immediate blood-red coloration with sodium diazobenzene-77-sulphonate in sodium carbonate solution. Found, in air-dried acid: loss at 110° = 20-7. CcH802N2,2H20 requires 20*5 per cent.
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