1-Propanol → 6-Aminoquinoline-5-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-amino-5-quinolinecarbonitrile (0.99 g, 5.9 mmol, prepared as described in Chem. Pharm. Bull., 1985, 33, 13260-1366) in 1-propanol (50 mL) was treated with 10 mL concentrated NaOH and heated to 100° C. for 18 hours. The mixture was concentrated, diluted with water, and washed twice with diethyl ether. The aqueous phase was acidified to pH 5 with 1M HCl and extracted with ethyl acetate in a continuous extractor. The organic extracts were dried (MgSO4), filtered, and concentrated to provide the desired product (0.55 g). MS (DCI) m/e 206 (M+NH4)+.

Provenance & Evidence