2-Methyl-8-hydroxyquinoline → 2-Methyl-1,2,3,4-tetrahydroquinolin-8-ol

Participants

Reaction Steps

7.50 g (47.0 mmol) of 8-hydroxy-2-methylquinoline were hydrogenated in an autoclave in the presence of 0.75 g of PtO2 in 60 ml of methanol at 4 bar of H2 and a temperature of 50° C. for 24 h. The reaction solution was filtered, and the filtrate was concentrated to dryness. The residue of 2-methyl-8-hydroxy-1,2,3,4-tetrahydroquinoline obtained was dissolved in 60 ml of ethanol, 3.85 ml of 37% strength formaldehyde solution and 1.1 g of Pd/C (10% strength) were added, and the reaction mixture obtained was hydrogenated in an autoclave at 4 bar of H2 and a temperature of 50° C. again for 24 h. It was filtered, the filtrate was concentrated, and the residue was purified by chromatography on SiO2 (EA/n-heptane 1:4). 1.56 g of the title compound were obtained.

Provenance & Evidence