The general procedure for the synthesis of 2,6-dimethyl-4-nitroaniline from N-(2,6-dimethyl-4-nitrophenyl)-4-methylbenzenesulfonamide is as follows: N-(2,6-dimethyl-4-nitrophenyl)-4-methylbenzenesulfonamide (3.2 g, 10.0 mmol) was dissolved in 32 mL of concentrated sulfuric acid and the reaction was heated for 1 hr at 50 °C. After completion of the reaction, the mixture was slowly poured into an ice-water mixture. The precipitate precipitated was collected by filtration and washed with cold water. The crude product was purified by recrystallization from ethyl acetate to give 2,6-dimethyl-4-nitroaniline (1.0 g, 53% yield) in yellow crystalline form. Thin layer chromatography (TLC) Rf value was 0.34 (unfolding agent: hexane/ethyl acetate, 5/1, v/v). Melting point: 164-165°C. 1H NMR (DMSO-d6, 400MHz) δ 7.79 (s, 2H), 6.16 (s, 2H), 2.16 (s, 6H). Mass spectrum (ESI) m/z: 166.8 [M+H]+, 188.8 [M+Na]+.
