Triethylamine → N-(Pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide

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Reaction Steps

3-Aminopyridine (0.424 g, 4.492 mmol), triethylamine (0.440 g, 4.342 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (0.735 g, 4.342 mmol) were added to a methylene chloride solution (200 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (1.120 g, 2.995 mmol) and the resulting solution was stirred at room temperature for 6 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to obtain the titled compound (0.710 g, 1.576 mmol, 53%).

Provenance & Evidence