Quinoline → 2-Amino-4-hydroxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

4-Amino-5-cyano-2-hydroxybenzoic acid (2.1 g, 11.79 mmol) is added to a quinoline solution already heated to 160° C. (12 ml) and the reaction solution is stirred at 180° C. for a further hour. After cooling, it is diluted with about 50 ml of a 1N sodium hydroxide solution. The mixture is extracted with dichloromethane. Subsequently, the aqueous phase is adjusted to pH 6.5 with hydrochloric acid and extracted with ethyl acetate and methanol (as a solubilizer). The combined organic phases are dried over sodium sulphate. The desired product is obtained after concentrating the solvents in 76% yield (1.2 g).

Provenance & Evidence