Pyridine → HCID 22407031, compound

Participants

Reaction Steps

Preparation of N-[3-(9-Fluorenyl)propionyl]-4-aminosalicylic acid hydrate was performed as follows. 2-(9-Fluorenyl)propionic acid (1.0 g, 4.2 mmol) was refluxed in 5 ml of thionyl chloride for 1.5 hours and the excess thionyl chloride evaporated in vacuo. The residue was dissolved in 10 ml of methylene chloride and added dropwise to a suspension of 4-aminosalicylic acid (0.64, 4.2 mmol) and pyridine (0.65 ml 8.4 mmol) in 15 ml of methylene chloride. After 3 hours, the reaction was concentrated, taken into ethyl acetate, washed with 10% HCl, and the organic layer dried with magnesium sulfate and concentrated to a tan solid which was purified by reverse phase flash chromatography (C18) eluting with methanol/water 50/50 then 70/30 to give a white solid, mp 225°-228° C. FTIR (KBr) 1643, 1511, 1450, 1367, 1257, 1167, 879, 830, 740, 671 cm-1. 1H NMR (300 MHz, DMSO) δ 1.92 (t, 2H, J=7.5 Hz), 2.35 (m, 2H), 4.09 (t, 1H, J=5.0 Hz), 6.92 (dd, 1H, J=8.5 Hz), 7.24-7.39 (m, 8H), 7.61 (m, 2H), 7.86 (d, 2H, J=7.5 Hz) 9.94 (s, 1H) . Anal. calcd for C23H19NO4 0.25H2O: C, 73.09; H, 5.20; N, 3.71. Found: C, 73.19; H, 5.30; N, 3.80.

Provenance & Evidence