22545-31-9Relevant academic research and scientific papers
The Rearragement of Aromatic Nitro Compounds. Part 1. The Reactions of Nitroanilines in Aqueous Sulphuric Acid
Murphy, J. Timothy,Ridd, John H.
, p. 1767 - 1772 (2007/10/02)
A number of substituted 2-nitroanilines rearange in concentrated sulphuric acid at 110 deg C to yield products that appear to be derived from 1,3-migration of the 2-nitro-group.For 2,3-dinitroaniline, the rate of reaction is almost independent of acidity over the range 83-97percent sulphuric acid and the solvent isotope effect k(H2SO4)/k(D2SO4) is 1.3-1.9.Methyl and t-butyl groups, when present as additional substituents in 2,3-dinitroaniline, have only a small effect on the reaction rate but 3-methyl-2-nitroaniline reacts much more slowly than 2,3-dinitroaniline.These results are discussed in terms of a rate-determining migration of the 2-nitro group following protonation at the 2-position.
