Steric effects on mesomerism: XIII. Preparation of 2,6‐dimethyl‐4‐nitroaniline
- 1 January 1954
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 73 (10) , 809-818
- https://doi.org/10.1002/recl.19540731004
Abstract
Nitration of 2,6‐dimethyl‐(p‐toluenesulpho) anilide or 2,6‐dimethyl‐benzenesulphoanilide in aqueous acetic acid, followed by deacylation, gives 2,6‐dimethyl‐4‐nitroaniline in yields of 80‐90%. These and other procedures are discussed.The rate of deacylation of 2,6‐dimethyl‐4‐nitroacetanilide in sodium methoxide solution is in agreement with the considerable steric inhibition of mesomerism to be expected.Keywords
This publication has 17 references indexed in Scilit:
- Preparation of 4‐nitro‐2,6‐xylidineRecueil des Travaux Chimiques des Pays-Bas, 1954
- An Interpretation of Meta Orientation in the Alkylation of Toluene. The Relative Reactivity and Isomer Distribution in the Chloromethylation and Mercuration of Benzene and Toluene1,2Journal of the American Chemical Society, 1953
- 160. The kinetics of aromatic halogen substitution. Part IX. Relative reactivities of monosubstituted benzenesJournal of the Chemical Society, 1953
- The Action of Acetic Anhydride on Benzalaniline. A ReinvestigationJournal of the American Chemical Society, 1951
- IDENTIFICATION OF AMINES. IV. METHANESULFONAMIDESJournal of the American Chemical Society, 1929
- CL.—The basic character of the acetoxylidides and its influence on the course of their substitutionJournal of the Chemical Society, 1927
- CXLVI.—The influence of nitro-groups on the reactivity of substituents in the benzene nucleus. Part VII. Reactions of 2 : 5- and 4 : 5-dinitro-m-xylenesJournal of the Chemical Society, Transactions, 1923
- Zur Kenntniss der Nitro‐ und Amido‐Derivate der XyloleEuropean Journal of Inorganic Chemistry, 1902
- Ueber Nitro‐ und Brom‐Derivate der XylidineEuropean Journal of Inorganic Chemistry, 1901
- Ueber die Nitrirung einiger aromatischer AmineEuropean Journal of Inorganic Chemistry, 1891