Sodium Hydroxide → HCID 23667717, compound

Participants

Reaction Steps

Then, a solution of 2-aminonicotinic acid (3.0 g, 21.7 mmol) in N,N-dimethylformamide (30 mL) was cooled with an ice water, 1-hydroxybenzotriazole (3.51 g, 26 mmol), (3-dimethylaminopropyl)-ethyl-carbodiimide (4.04 g, 26 mmol) and a solution of the resulting 4-aminomethyl-phenol (3.0 g, 21.7 mmol) in N,N-dimethylformamide (20 mL) were added, and the solution was stirred for 18 hours at this temperature. The reaction solution was partitioned into brine, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was dissolved in ethyl acetate, filtration was carried out using NH silica gel, and the filtrate was concentrated. The residue was dissolved in methanol (90 mL), 1N sodium hydroxide (17.8 mL, 17.8 mmol) was added thereto, followed by stirring at room temperature for an hour and a half. The reaction solution was concentrated in vacuo, and the title compound (5.66 g) was obtained as a pale yellow solid.

Provenance & Evidence