Uses
7-Hydroxy-1-tetralone, its derivatives and related fluorescent chalcones have been used as pharmacological tools to study the human histamine H3 receptor. Also C7-Substituted α-Tetralone derivatives have been study as Inhibitors of Monoamine Oxidase.
Synthesis
Under nitrogen protection, 7-methoxy-3,4-dihydronaphthalen-1(2H)-one (25 g, 142 mmol) was slowly added to a suspension of anhydrous toluene (250 mL) containing aluminum trichloride (37.8 g, 283 mmol). The reaction mixture was heated with stirring at 110 °C for 1 hour and then cooled to room temperature. Subsequently, the mixture was further cooled to 0 °C (under ice bath conditions) and water (100 mL) was slowly added to quench the reaction. The organic material in the aqueous phase was extracted with ethyl acetate (100 mL x 3), the organic phases were combined and dried with anhydrous magnesium sulfate. After filtration to remove the desiccant, the filtrate was concentrated to dryness under reduced pressure. The crude product was ground with methanol to give 19.3 g of white solid in 90% yield. The product required further purification. Thin layer chromatography (TLC) analysis (unfolding agent ratio 3:7 ethyl acetate/hexane) showed a single spot with an Rf value of 0.26. The melting point of the product was measured to be 164-166 °C (literature value 165-167 °C).
References
[1] Journal of Medicinal Chemistry, 1998, vol. 41, # 7, p. 1068 - 1083
[2] Tetrahedron Letters, 1997, vol. 38, # 50, p. 8749 - 8752
[3] Tetrahedron Letters, 2014, vol. 55, # 3, p. 682 - 685
[4] Patent: US6248766, 2001, B1
[5] Patent: US2008/280991, 2008, A1. Location in patent: Page/Page column 37
