Tetrahydrofuran → Benzamide

Participants

Reaction Steps

As shown in reaction scheme 2 above, after cooling a solution of 5-aminoquinoline represented by Formula 84 (439.93 mg, 3.05 mmol, purchased from TCI Co.) and triethylamine (0.95 mL, 6.78 mmol) in THF (10 mL) at 0° C. under a nitrogen atmosphere, a solution of 4-n-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 (1.04 g, 3.39 mmol) in THF (15 mL) was slowly added to the above cold solution. After agitating the prepared solution at the same temperature for 30 minutes, this solution was left at room temperature for 18 hours. After filtering and removing a precipitate generated during the reaction, the remaining solution was diluted with chloroform and washed with a potassium carbonate solution, followed by separation and drying with (anhydrous) sodium sulfate. A concentrate remaining after removing the solvent under reduced pressure was recrystallized using ethyl acetate and hexane, resulting in a benzamide compound represented by Formula 2 as a desired product (VVZ-001; 1.08 g, 77% yield).

Provenance & Evidence