Oxalic Acid → (E)-3-Methoxystyryl-1-(2-pyridyl)-1H-benzimidazole oxalate

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Reaction Steps

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and 3-methoxycinnamoyl chloride (Amino, Y.; Kawada, K.; Toi, K.; Kumashiro, I.; Fukushima, K. Chem. Pharm. Bull., 1988, 36, 4426) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate/n-hexane yielded the titled compound. MW: 417.42; mp: 163.0-164.0° C.; 1H-NMR (DMSO) δ: 8.78 (1H, dd, J=4.9, 1.3 Hz), 8.19 (1H, td, J=7.9, 2.0 Hz), 7.87 (1H, d, J=15.8 Hz), 7.77-7.72 (2H, m), 7.67-7.61 (1H, m), 7.48-7.44 (1H, m), 7.36-7.24 (3H, m), 7.22-7.15 (3H, m), 6.96-6.92 (1H, m), 3.78 (3H, s).

Provenance & Evidence