This product, known technically as cresidine, was first obtained by Hofmann and Miller [Ber., 14, 573 (1881)]. Before the present work, however, only two substitution products had been obtained from it, viz., the 6-nitro and the 6-chloro derivatives. In this work a monobrom derivative has been prepared and its structure established. It readily forms a quaternary ammonium iodide, therefore the bromine atom does not occupy position 2, adjacent to the amino group, as this would hinder the formation of such a salt. 3-5-Dibrom-4-methoxytoluene was synthesized and found to be different from the dibrom derivative obtained from the compound in question by replacement of the amino group by bromine. This leaves the structure of the monobrom derivative as 3-amino- 4-methoxy-6-bromotoluene. The new bromine compound was characterized by the preparation of the following derivatives: 3-acetylamino-4-methoxy-6-bromotoluene, 3-benzoylamino-4-methoxy-6-bromotoluene (3-acetylamino-4-methoxy-6-bromobenzoic acid.)
Proceedings of the Iowa Academy of Science
©1929 Iowa Academy of Science, Inc.
Raiford, L. Chas. and Grosz, Oliver
"Derivatives of 3-Amino-4-Methoxytoluene,"
Proceedings of the Iowa Academy of Science, 36(1), 268-268.
Available at: https://scholarworks.uni.edu/pias/vol36/iss1/58