Uses
2,4-Dimethyl-6-nitroaniline is used as a reagent in the synthetic preparation of 1,2-bis-substituted benzimidazoles as nonnucleoside HIV-1 reverse transcriptase inhibitors.
Synthesis
General procedure for the synthesis of 2-nitro-4,6-dimethylaniline from 2,4-dimethylaniline: 2,4-dimethylaniline (8.0 g, 66.0 mmol) was dissolved in acetic anhydride (50 mL) and concentrated nitric acid (5 mL) was added slowly and dropwise at 0 °C. The reaction mixture was stirred at 0 °C for 30 min and then diluted with ice water (200 mL). Subsequently, concentrated hydrochloric acid (10 mL) was added dropwise to the mixture and the resulting mixture was stirred under reflux conditions for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The residue was diluted with aqueous ammonium hydroxide and the resulting orange solid was filtered and dried to give 2-nitro-4,6-dimethylaniline (10.6 g, 97% yield).
References
[1] Patent: WO2009/25478, 2009, A1. Location in patent: Page/Page column 33; 52-53
[2] Patent: US2010/197673, 2010, A1. Location in patent: Page/Page column 15
[3] Patent: KR101511771, 2015, B1. Location in patent: Paragraph 0406; 0407
[4] Tetrahedron Asymmetry, 2003, vol. 14, # 10, p. 1267 - 1273
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 21, p. 8743 - 8749
