Citric Acid → 2-(2-Quinolylmethoxy)-5-pyridylmethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-quinolylmethoxy)nicotinic acid (4.38 g, 1.56 mmol), prepared as in step 3, and triethylamine (0.228 ml, 1.64 mmol) in THF (80 ml) at -10° C. to -5° C. was added dropwise a solution of ethyl chloroformate (1.57 ml, 1.64 mmol) in THF (5 ml), and the reaction mixture was stirred at 0° C. for 1 hour. Precipitated triethylamine hydrochloride was filtered and washed with THF. The combined filtrate and washings were placed in an addition funnel and added dropwise to a mixture of sodium borohydride (1.50g, 3.91 mmol) in water (20 ml) at 0° C. When the bubbling ceased, the mixture was allowed to warm to room temperature and stir for 2 hours. 10% Citric acid added to bring the mixture to pH 3 and the aqueous layer was extracted with ethyl acetate. The organic extract was washed with 1N NaOH, water, and brine, and dried over MgSO4. The solvent was removed in vacuo and the residue treated with ethyl acetate-hexane to precipitate the product, 3.44 g of 6-(2-quinolylmethoxy)pyrid-3-ylmethanol.

Provenance & Evidence