Y. Hashimoto, M. Degawa
Apr 30, 1975
Citations
0
Influential Citations
4
Citations
Journal
Gan
Abstract
As in the cases of other carcinogenic aromatic amines,1-7) O-ester(s) of N-hydroxy-4-(methylamino)azobenzene has been estimated as an ultimate carcinogen(s) in the neoplastic process induced by the potent hepatocarcinogen, 4-(dimethylamino)azobenzene.5,8) For this study, N-hydroxy-4(methylamino) azobenzene (I) is a basic compound, but its synthesis has been unsuccessful because of its unstability. This communication deals with the synthesis of I and its 4'-methoxycarbonyl derivative (II) by alkaline hydrolysis of the corresponding N-benzoyloxy compounds in the presence of an antioxidant, ascorbic acid, and with the synthesis of acetates (III and IV) of I and II. Reactivity of these synthetic products to several amino acids is also described. N-Benzoyloxy-4-(methylamino) azobenzene8) (V) and its 4'-methoxycarbonyl derivative (VI) were synthesized from the corresponding 4-methylaminoazo dyes by the method described by Poirier et al.8) A solution of 20ml of 5N KOH containing 50mg ascorbic acid was added to 200mg of V or VI dissolved in 80ml ethanol. The reaction mixture, which colored bluish, was kept for 5min at room temperature, neutralized with 1N HCl solution, and then extracted twice with 100ml ethyl acetate. Organic phase was washed with NaHCO3 solution and then with water, dried over anhydrous Na2SO4, and evaporated to dryness at