[Synthesis]
The general procedure for the synthesis of (2-amino-5-(trifluoromethyl)phenyl)methanol from 2-amino-5-trifluoromethylbenzoic acid was carried out as follows: firstly, compound 24a was prepared from compound 22b according to the literature method, which was followed by the synthesis of the target product 28b. The yield of this step was 84% and the product was a yellow amorphous solid. The main absorption peaks were located at 3389, 2918, 1461, 1274, 1122 cm-1 as detected by infrared spectroscopy (IR, KBr). nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300 MHz, CDCl3) showed δ-values: 1.26-1.34 (1H, m), 2.09 (1H, dt, J = 5.1, 12.6 Hz), 2.27 ( 1H, dt, J = 2.4, 12.0 Hz), 2.39-2.50 (1H, m), 2.43 (3H, s), 2.89 (1H, d, J = 6.3 Hz), 2.96-2.99 (2H, m), 3.08 (1H, d, J = 17.7 Hz), 3.27 (1H, d, J = 17.7 Hz), 3.49 (1H, d, J = 17.4 Hz), 1H, d, J = 17.7 Hz), 3.49 (1H, d, J = 17.4 Hz), 3.09 (1H, dt, J = 5.1, 12.6 Hz) d, J = 17.4 Hz), 3.69 (1H, d, J = 17.7 Hz), 6.68 (1H, dd, J = 2.1, 8.3 Hz), 7.01 (2H, d, J = 8.3 Hz), 7.04 (1H, d, J = 2.1 Hz), 7.28 (1H, d, J = 8.3 Hz), 7.58 (1H, s), 7.63 ( 1H, s), where two protons (OH) were not observed. The nuclear magnetic resonance carbon spectrum (13C NMR, 75 MHz, CDCl3) showed δ-values: 23.9, 35.8, 36.1, 38.8, 40.3, 42.9, 45.4, 61.5, 69.3, 113.1, 115.2, 123.78 (q, J = 270.5 Hz), 123.79 (q, J = 3.1 Hz), 124.5 (q, J = 4.3 Hz), 125.7, 126.8, 127.0 (q, J = 32.3 Hz), 127.7, 129.0, 129.9, 136.6, 140.4, 145.9, 155.4, 160.0. High-resolution mass spectrometry (HRMS, ESI) showed that the calculated values of [M + H]+ were C25H24F3N2O2, 441.1790; the measured value was 441.1775. |