Tetrahydrofuran → HCID 20340829, compound

Participants

Reaction Steps

27 g. of 4,6-dichloroquinoline-5-carboxylic acid, ethyl ester (0.1 mol.) are dissolved in 600 ml. of anhydrous tetrahydrofuran. Nitrogen is passed through the flask and while stirring and cooling to 0°, 2.4 g. of lithium aluminum hydride are added a bit at a time in order to keep the reaction temperature at 0° to +5°. Stirring is continued for an additional five hours. Then 2.5 ml. of water, 2.0 ml. of aqueous sodium hydroxide (20%) and again 9 ml. of water are added. The precipitated inorganic salts are filtered off and the solvent is removed by a rotary evaporator. The resulting oil is dissolved in a small quantity of benzene and kept in the refrigerator. The crystallized 4,6-dichloroquinoline-3-methanol is filtered off and recrystallized from ethyl acetate; yield: 12.5 g. (55%); m.p 182°.

Provenance & Evidence