LXI.—The dinitrotoluidines

Oscar Lisle Brady, James Nelson Edmund Day, William Joseph Woodgate Rolt
1922 Journal of the Chemical Society Transactions  
DURING: the course of earlier investigations on the synthesis of 2 : 3 : 6-trinitrotoluene (Brady and Taylor, T., 1920, 117, 876) and of 3 : 4-dinitrotoluene (Brady and Williams, ibid., p. 1137), a marked difference was observed in the behaviour of some of the dinitrotoluidines on diazotisation and on oxidation with monopersulphuric acid, depending, apparently, on the relative positions of the groups. This seemed to offer an opportunity for the study of the effect of the position and number of
more » ... tion and number of other substituents on the reactivity, apart from mobility, of the amino-group in the benzene ring. The present paper is an account of preliminary preparative work. Sixteen dinitrotoluidines should exist ; of these, eleven have been described, and two others have been prepared by other workers, although their results have not yet been published. Three, therefore, remained, namely, 2 : 5dinitro-m-toluidine, 4 : 5-dinitro-m-toluidine, and 5 : 6-dinitro-mtoluidine. An attempt has been made; to prepare these three
doi:10.1039/ct9222100526 fatcat:edyr2ncudnb2pnm543lknyihwa