Chemical Properties
Off-white solid
Uses
2,6-Dimethylaniline degradation by Fenton process has been studied in depth for the purpose of learning more about the reactions involved in the oxidation of 2,6-dimethylaniline under various reaction conditions. Using a previously developed gas chromatographic-mass spectrometric assay, hemoglobin adducts of 2,6-dimethylaniline were detected covalently bound to rat hemoglobin after administration of either 2,6-dimethylaniline or lidocaine.
Synthesis
N-hydroxy-2,6-dimethoxybenzamide (1a) (0.237 g, 1.2 mmol) was used as a raw material and it was mixed with K2CO3 (0.166 g, 1.2 mmol) and DMSO (0.5 mL). Acetic anhydride (1.1 mL, 0.012 mmol) was added to the mixture and the reaction system was heated to 50°C. After stirring the reaction at this temperature for 10 min, the reaction mixture was cooled to 0°C and subsequently treated with 2M HCl (~2 mL). After the mixture was transformed into a clarified solution, it was neutralized by the addition of 2M NaOH (ca. 2 mL) and subsequently extracted with ether (Et2O, 15 mL x 3). The organic layers were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ether, 1:1) to afford the target product 2,6-dimethoxyaniline (2a) (0.171 g, 93% yield) as a white crystalline solid.
References
[1] Chemical Communications, 2009, # 17, p. 2281 - 2283
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 9046 - 9054
[3] Tetrahedron Letters, 2015, vol. 56, # 5, p. 710 - 712
