5-Methyl-8-hydroxyquinoline

Tiliquinol is a hydroxyquinoline.|Tiliquinol is an antiprotozoal agent that was used in combination with tibroquinol. The combination agent was withdrawn from the market because of hepatoxicity.

General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 °C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7−8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15percent ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.Following the procedure reported in and using 5- methyl-8-hydroxy-quinoline (3b, 1.0 mmol, 0.159 g synthetized according to J. H. Burckhalter , R. I. Leib J. Org. Chem. 1961, 26, 4078-4083), 4b has been obtained as a pale yellow solid in 99percent yield (0.30 g, 0.49 mmol), and with a purity higher than 95percent, as judged by 1H- MR analysis. Example 5Following the procedure reported in and using 5- chloro-8-hydroxy-quinoline (3c, 1.0 mmol , 0.18 g - Sigma Aldrich) , 4c has been obtained as a pale yellow solid in 96percent yield (0.31 g, 0.48 mmol), and with a purity higher than 95percent, as judged by ''H-NMR analysis.

Molecular Weight:159.18
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:159.068413911
Monoisotopic Mass:159.068413911
Topological Polar Surface Area:33.1
Heavy Atom Count:12
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes