NOTE ON THE REACTION OF d-GLUCOSAMINE WITH o-PHENYLENEDIAMINE

In extending the benzimidazole method for the identification of aldoses (1,2) and hexuronic acids (3) to other members of the sugar series, we have attempted to prepare the benzimidazole derivative of d-glucosamine.Condensation of d-glucosaminic acid prepared by the method of Pringsheim and Ruschmann (4) with o-phenylenediamine under a variety of conditions failed to yield a crystalline product.The direct oxidative condensation of d-glucosamine hydrochloride with o-phenylenediamine in the presence of cupric acetate ( 5) yielded a crystalline quinoxaline and not a benzimidazole.The quinoxaline was originally obtained by Griess and Harrow (6).Ohle ( 7), who prepared it by condensing d-fructose with o-phenylenediamine, showed that it is 3-(Darabo-tetrahydroxybutyl)quinoxaline.EXPERIMENTAL