Pyridine → HCID 2676472, compound

Participants

Reaction Steps

To a solution of methyl 4-aminobenzoate (500 mg, 3.31 mmol) in anydrous pyridine (10 mL) was added dropwise 4-cyanobenzoyl chloride (660 mg, 4.0 mmol) at 0° C. After 5 min the temperature was allowed to warm up to rt. After 3 hrs aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 720 mg) was added and the resulting mixture was stirred overnight at rt. After rinsing the resin and filtration, water (25 mL) was added to the filtrate and a beige solid precipated out. Filtration and washing with water gave a solid which was dried under vacuo at 60° C. for 5 hrs. The title compound (774 mg) was obtained as a beige solid (83%) in 97.7% purity by HPLC (MaxPlot detection between 230 and 400 nm) 1H NMR (300 MHz, DMSO-d6) δ 10.68 (s, 1H), 8.45 (m, 1H), 8.12 (d, J=8.3 Hz, 2H), 8.05 (m, 3H), 7.71 (d, J=7.8 Hz, 1H), 7.52 (dd, J=7.9, 7.8 Hz, 1H), 3.86 (s, 3H).

Provenance & Evidence