N-butyl-2-hydroxybenzamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.0 g (65.7 mmol) of methyl salicylate and 33 ml of n-butylamine were dissolved in 100 ml of methanol, followed by heating at reflux for 8 hours while stirring. Methanol was distilled off under reduced pressure, and the residue was acidified by adding an aqueous 2 N hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed in turn with water and saturated sodium hydrogen carbonate, and then dried over anhydrous magnesium sulfate. The organic layer was filtered, and the filtrate was concentrated under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (eluant hexane/ethyl acetate=10/1 to 5/1) to obtain 10.0 g (yield: 79%) of salicylic acid n-butylamide as an oily substance. 1H—NMR spectrum data of salicylic acid n-butylamide are as follows. by heating at reflux for 8 hours Methanol was distilled off under reduced pressure by adding an aqueous 2 N hydrochloric acid followed by extraction with dichloromethane The organic layer was washed in turn with water and saturated sodium hydrogen carbonate dried over anhydrous magnesium sulfate The organic layer was filtered the filtrate was concentrated under reduced pressure the resulting residue was purified by silica gel column chromatography (eluant hexane/ethyl acetate=10/1 to 5/1)