General procedure for the synthesis of 2-(2-hydroxymethyl)quinoline from ethyl 2-quinolineacetate: ethyl 2-quinolineacetate (8.6 g, 42.8 mmol) was dissolved in ether (400 mL) and cooled to -78 °C. At -78 °C, lithium aluminum hydride (1.63 g, 42.8 mmol) was added in batches. After maintaining -78 °C for 2 hours of stirring, the temperature was slowly increased to 0 °C and stirring was continued at 0 °C for 4 hours, followed by stirring at room temperature overnight. Upon completion of the reaction, the mixture was cooled to 0 °C and a small amount of methanol was added to quench unreacted lithium aluminum hydride, followed by sodium sulfate decahydrate (43 g). After stirring for 1 h at room temperature, the reaction mixture was filtered, the solid residue was washed with chloroform, and the filtrates were combined and concentrated. Purification by silica gel column chromatography (eluent ratio 2:1 ethyl acetate-hexane) afforded 0.46 g (53% yield) of 2-(2-hydroxymethyl)quinoline. The product was confirmed by 13C NMR (101 MHz, chloroform-D) with chemical shifts of δ 161.53, 147.23, 137.04, 130.01, 128.74, 127.79, 127.03, 126.39, 122.09, 61.60, 39.52 ppm; mass spectrometry (AP/CI) showed the molecular ion peak m/z 174.2 (M + H)+.
