HCID 58964594, compound → HCID 24284802, compound

Participants

Reaction Steps

To a 1 L pressure vessel was added crude 2-Benzyloxy-N-(3-trifluoromethyl-phenyl)-acetamide (˜10 g) and methanol (400 mL). The solution was purged with N2. 10% Pd/C (1.1 g) was added. The vessel was placed under H2 atmosphere at 50 psi for 2.5 h. LC/MS analysis shows only partial hydrogenolysis of the benzyl ether, so Pd(OH)2H2O (2 g) was added and the vessel is placed again under H2 atmosphere at 50 psi for 2.5 h. The reaction mixture was filtered through a pad of Celite and concentrated to give a brown oil. The crude material was purified via flash chromatography (1:1 EtOAc/Hexanes) to give 2-hydroxy-N-(3-trifluoromethyl-phenyl)-acetamide as a white solid (5.27 g, 84% yield, two steps). LC/MSD (HP Series 1100 MSD) Expected MW: 219.05, Observed M+H, 220.0, Retention time: 1.22. 1H-NMR, DMSO-d6, Varian 400 MHz δ 10.07 (s, 1H), 8.22 (s, 1H), 7.97 (dd, 1H), 7.55 (t, 1H), 7.41 (m, 1H), 5.76 (t, 1H), 4.03 (d, 2H) ppm.

Provenance & Evidence