Triazines and related products. Part V. The structure of some red N-alkyl-1,2,3-benzotriazines

Alkylation of 4-arylamino-1,2,3-benzotriazines with alkyl iodides in ethanol affords the N-2 alkyl iodides which on basification yield the deep-red anhydro-2-alkyl-4-arylamino-1,2,3-benzotriazinium hydroxides. In contrast alkylation in sodium ethoxide solution affords isomeric products substituted at N-2 and N-3. The site of alkylation of the N-2 substituted series has been confirmed by reduction studies; hydrazine in ethanol containing Raney nickel efficiently degrades the triazine ring. The chemical and spectroscopic properties of the red triazines have been investigated.