o- and p-Toluenazoglyoxalines / by Frank Lee Pyman and Leonard Allan Ravald.

  • Pyman, Frank Lee.
Date:
[1920?]
Catalogue details

Licence: In copyright

Credit: o- and p-Toluenazoglyoxalines / by Frank Lee Pyman and Leonard Allan Ravald. Source: Wellcome Collection.

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    CLVL—o- and p» Toiueneazoglyoxalines. By Frank Lee Pyman and Leonard Allan Ravald. In continuation of previous work on arylazoglyoxalines (Fargher and Pyman, T., 1919, 115, 217), the interaction of o- and p-toluenediazonium chlorides and glyoxaline has been studied. The methods employed and the products obtained are generally similar to those described in the previous communication. o-Toluenediazonium chloride combines with glyoxaline in aqueous sodium carbonate, giving 2-o-tolueneazoglyoxaline (I) in poor yield, a considerable amount of bis-o-tolueneazo-o-cresol being produced as a by-product. On replacing the sodium carbonate by sodium hydroxide, the yield was very little better, but the by¬ products were ot different character, whilst when sodium hydrogen carbonate was used in the place of sodium carbonate, bis-o-toluene- azo-o-cresol was again produced, but no tolueneazoglyoxaline. ' o ~ Tolueneazoglyoxaline resembles 2 - benzeneazoglyoxaline closely m physical and chemical properties. On reduction with stannous chloride, it gives 2 -diaminoA-m-tolylglyoxaline (II). CH-NR X 11 r>c*^:N< CH—1ST* OH \ SH.\ CH-NH OH. \ i C- ■N >cah5 (!) (II.) The combination of £?-toluenediazonium chloride with glyoxaline in aqueous sodium carbonate leads to the formation of 2-p-toluene- azoglyoxahne (III) in good yield, together with a small amount