Methanol → HCID 15597531, compound

Participants

Reaction Steps

With stirring, a mixture of 44.0 g of 3-hydroxyaniline, 60.0 g of 2-vinylpyridine, 140.0 ml of methyl alcohol and 5.0 ml of glacial acetic acid was maintained at reflux temperature for approximately twenty-four hours. The methyl alcohol was removed by distillation and a mixture of water and toluene was added to the resultant residue. Three layers resulted. Sufficient 5 percent aqueous sodium hydroxide was added to adjust the water layer to approximately pH 7.0. The bottom oil layer was separated and dried under reduced pressure to obtain a gummy solid which was triturated with hexane to obtain 69.0 g of N-[2-(2-pyridyl)ethyl]-3-hydroxyaniline (Formula V: R4 =R9 =H; R10 =OH), a pale tan solid which, after being exposed to air, turned into a taffy-like solid. The nuclear magnetic resonance spectrum was concordant with the assigned structure. The water layer was discarded. The toluene layer was washed first with water and then with saturated sodium chloride solution and evaporated to dryness under reduced pressure. The residue was recrystallized from a mixture of ispropanol and hexane to obtain 3.9 g of N-[2-(2-pyridyl)ethyl]-3-hydroxyaniline, a white solid which melted at 118° to 120° C. A significant infrared maximum appeared at 1195 cm-1 (N-C;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure.

Provenance & Evidence