Sodium Hydroxide → HCID 58374131, compound

Participants

Reaction Steps

To a solution of ethyl 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylate (1.2 g, 4.21 mmol) in EtOH (20 mL) was added a predissolved solution of sodium hydroxide (1.00 g, 25.1 mmol) in water (5.00 mL). The reaction mixture was stirred overnight at room temperature. The next day, the reaction mixture was concentrated in vacuo, acidified with dilute HCl, and extracted from 1 M HCl with EtOAc. Some product did extract but the aqueous layer remained yellow with desired product as well. The aqueous layer was brought to pH 5 using ammonium hydroxide and NH4Cl and extracted with EtOAc again which afforded additional product. The combined organic layers were dried over MgSO4, filtered, concentrated to give 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylic acid (140 mg, 0.544 mmol, 12.94% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.5 (1H, br s), 8.69 (1H, dd), 8.35 (s, 1H), 8.14 (1H, dt), 7.78 (1H, d), 7.67 (1H, dt).

Provenance & Evidence