Sodium Hydroxide → HCID 68632314, compound

Participants

Reaction Steps

To a mixture of methyl 3-(3,5-dichloro-4-(4-methoxybenzyloxy)phenyl)-1H-pyrazole-5-carboxylate (0.75 g, 1.85 mmol) in a mixture of THF (10 mL) and methanol (10 mL) was added 15% w/v solution of sodium hydroxide (5 mL). The mixture was stirred at room temperature for 30 minutes followed by heating at reflux for 2 h. After this time the flask was cooled to room temperature and solvent was removed in vacuo. The residue was partitioned between ethyl acetate (20 mL) and water (100 mL). The aqueous layer was acidified to pH 1 (10 M HCl, 1.5 mL) and the precipitated solids dissolved in ethyl acetate (30 mL). The organic layer was washed with an aqueous solution of sodium chloride (65 mL) and dried (MgSO4). The solution was concentrated to give 0.69 g (96%) of the Compound C as a white solid. 1H NMR δ (ppm) (DMSO-d6): 3.81 (3H, s), 5.02 (2H, s), 7.00 (2H, d, J=8.24 Hz), 7.41 (1H, s), 7.48 (2H, d, J=8.24 Hz), 8.03 (2H, s), 14.09 (1H, br s). CO2H peak not observed.

Provenance & Evidence