3-Hydroxyanthranilic Acid → HCID 67424503, compound

Participants

Reaction Steps

2-amino-3-hydroxybenzoic acid (2 g, 13 mmol) was dissolved in 20 ml of DMF and at 0° C. EDCI (2.7 g, 1.2 equiv.), hydroxybenzotriazole (1.9 g, 1.2 equiv.) and 4-trifluoromethylbenzylamine (2 ml, 1.2 equiv.) were added. The mixture was stirred at rt for 20 hours. The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from EtOAc/ether gave 3.5 g of a beige solid. Yield=86% 1HNMR (DMSO, 200 MHz) δ 4.49 (2H, d, J=5.6 Hz), 6.00 (2H, bs), 6.41 (1H, t, J=8 Hz), 6.76 (1H, d, J=7.6 Hz), 7.11 (1H, d, J=8.2 Hz), 7.51 (2H, d, J=8 Hz), 7.69 (2H, d, J=8 Hz), 8.81 (1H, bt), 9.58 (1H, bs); [M+1] 311.1 (C15H13F3N2O2 requires 310.27).

Provenance & Evidence