Quinoline-5-carboxylic acid → (Quinolin-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of quinoline-5-carboxylic acid (500 mg, 2.83 mmol) in THF (10 mL) was added slowly LiAlH4 (1.0 M, THF) solution at 0° C. The resulting residue was heated to 70° C. for 3 h and stirred at room temperature for 16 h. The reaction mixture was cooled to 0° C. and quenched with water (1 mL) and 10% NaOH (1.5 mL) solution. The reaction mixture was stirred for 1 h. The solution was filtered through a pad of celite and rinsed with THF. The filtrate was concentrated and the resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 218 mg of quinolin-5-yl-methanol (48%).

Provenance & Evidence