Methyl 4-aminobenzoate → Methyl 4-{[4-(hexyloxy)benzoyl]amino}benzoate

Participants

Reaction Steps

To a solution of methyl 4-aminobenzoate (500 mg, 3.31 mmol) in anhydrous pyridine (10 mL) was added dropwise 4-(hexyloxy)benzoyl chloride (890 μL) at 0° C. After 5 min the temperature was allowed to warm up to rt. After 90 min aminomethyl resin (Polymers Laboratories PL-AMS, 1.93 mmol/g, 720 mg) was added and the resulting mixture was stirred overnight at rt. After filtration and rinsing the resin, water (125 mL) was added to the filtrate and a white solid precipated out. Filtration and washing with water gave a solid which was dried under vacuo at 60° C. overnight. The title compound (1073 mg) was obtained as a white solid (91%) in 99.7% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Provenance & Evidence