Hydrochloric Acid → HCID 9816112, compound

Participants

Reaction Steps

4,6-Dichloro-3-hydroxy-5-methyl-2nitrobenzoic acid (69 mg, 0.26 mmol) was dissolved in HOAc (10 mL), 10% Pd/C (10 mg) and concentrated HCl (33μ, 0.39 mmol) were added. Hydrogenation at room temperature and at atmospheric pressure for 2 h gave a slurry to which methanol (5 mL) was added and the catalyst was filtered off. Evaporation of the solvent, co-evaporation with toluene (10 mL) followed by vacuum-drying over KOH gave 63 mg of a crude product. Purification by flash column chromatography (SiO2), EtOAc-HOAc 45:1) yielded 55 mg of the title compound. Mp: 192° C. (dec); 1H NMR (DMSO-d6): δ 2.27 (s, 3H); 13C NMR (DMSO-d6): δ 167.43, 139.25, 136.01, 122.90, 121.26, 120.37, 116.89, 16.96; MS (EI, 70 eV): m/z (rel.int.) 237/235 (M+, 45/79), 219/217 (37/64), 191/189 (60/100).

Provenance & Evidence