Synthesis
Step 3: Synthesis of 2-nitro-3-(trifluoromethyl)aniline; N-(2-nitro-3-(trifluoromethyl)phenyl)acetamide (0.9 g, 3.6 mmol) was dissolved in ethanol (23 mL), followed by addition of 20% aqueous sodium hydroxide solution (4.5 mL). The reaction mixture was heated to reflux for 1 hour. Upon completion of the reaction, it was cooled to room temperature and the solvent was removed by evaporation. The residue was diluted with water (50 mL) and extracted with ethyl acetate (2 x 25 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to dryness to give 2-nitro-3-(trifluoromethyl)aniline as a yellow solid (0.67 g, 95.54% yield).1H NMR (300 MHz, DMSO-d6): δ (ppm) = 7.4-7.3 (m, 1H), 7.3 (d, J = 12Hz, 1H), 7.4-6.8 (m, 1H), 5.00 (pp. 1H), 5.00 (bs, 2H).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 2, p. 526 - 530
[2] Patent: WO2010/115736, 2010, A2. Location in patent: Page/Page column 101
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 23, p. 190
[4] Bulletin de la Classe des Sciences, Academie Royale de Belgique, 1927, vol. <5> 13, p. 349
[5] Chem. Zentralbl., 1927, vol. 98, # II, p. 1817
