Hydrochloric Acid → HCID 86688235, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl 5-aminoisophthalate (Aldrich, 3.28 g, 15.7 mmol) and triethyl amine (3.4 mL, 24.7 mmol) were dissolved in dry tetrahydrofuran (90 mL) under inert atmosphere and cooled to 0° C. for at least 30 min. A solution of palmitoyl chloride (5 mL, 16.5 mmol) in THF (25 mL) was then added slowly, dropwise. The reaction was then allowed to warm slowly to room temperature and stirred for at least 1 h before deionized water (10 mL) was added and the tetrahydrofuran was removed by rotary evaporation. The crude residue was then suspended in deionized water (50 mL), filtered, washed with deionized water, and dried to give a white solid. The crude solid was then dissolved in refluxing methanol (200 mL). Potassium hydroxide (˜85%, 5.76 g, 0.102 mol) and deionized water (50 mL) were then added. After 1 h, the reaction was cooled to room temperature to give a cloudy white suspension. 5M HCl (25 mL) was added until the pH of the slurry was acidic, and the solid was filtered, washed with deionized water, and dried in vacuo to give a white solid (6.45 g, 98%). The product was identified by 1H and 13C NMR spectroscopy and ESI-MS and was of satisfactory purity. The product was believed to be of the formula

Provenance & Evidence