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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    In acid dried at 110°, C = 51*3; H = 5*7; N = 19*9. C6H802N2 (140’1) requires C = 51'4; H = 5*8; N = 20*0 per cent. The 'picrate crystallises from water in large, prismatic needles containing one and a-lialf molecules of water of crystallisation. After drying at 60° in a vacuum, it sinters above 170° and forms a turbid liquid, which becomes clear at about 195°. Found, in air-dried salt, H20 = 6'9. C6H802N2,C6H307N3,1JH20 requires 6'8 per cent. In dried salt, N = 18'7. ‘C6H802N2,CcH307N3 (369-2) requires N = 19-0 per cent. Ethyl 2-ethylglyoxaline-A-carboxylate crystallises from ethyl acetate, in which it is readily soluble, in prismatic needles which melt at 129° (corr.), and are anhydrous. It is readily soluble in alcohol, but sparingly so in water. It gives no coloration with sodium diazobenzene-p-sulphonate in sodium carbonate solution. Found: 0 = 56*8; 11 = 7-2; N = 16’5. C8IT1202N2 (168'2) requires C = 57’l; TI = 7• 2 ; N = 16‘6 per cent. 2-PhenylglyoxalineA-carboxylic Acid and its Derivatives. 2-Phenylglyoxaline-^-carboxyanilide is prepared by the action of boiling aniline on 2-phenylglyoxaline-4:5-dicarboxylic acid in a yield amounting to 74 per cent, of the theoretical. As it is prac¬ tically insoluble in boiling water, it is left behind after the steam distillation somewhat contaminated by resinous impurities, which are readily removed by grinding and washing with ice-cold alcohol. It is sparingly soluble in alcohol or the other usual organic solvents, and separates from alcohol in minute, glistening needles, which melt at 263° (corr.) and are anhydrous. It gives no coloration with sodium diazobenzene-p-sulphonate in sodium carbonate solution. Found: C = 72'6; H = 5*3; N = 15*9. Ci6Hi3ON3 (263'2) requires C = 73-0; H = 5-0; N = 16'0 per cent. 2-Phenylglyoxaline-‘i-carboxylic acid is obtained in good yield by the hydrolysis of the corresponding anilide, which, however, is much more stable towards acid hydrolysis than the 2-alkyl derivatives. At 130° the reaction proceeds very slowly, but at 145—150° the reaction is ‘complete after eight to nine hours’ heating. The acid separates from boiling water, in which it is fairly readily soluble, in fan-shaped clusters of minute needles containing one and a-half molecules of water of crystallisation. After drying at 110°, it melts and effervesces at 239° (yorr.). The acid gives an immediate