Sodium Hydroxide → 4-(5-Hydroxypyridin-3-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.9 g (9.02 mM) of 4-(5-methoxy-3-pyridinyl)benzonitrile and 6.39 g (54.2 mM) of pyridinium hydrochloride is heated at 160° C. for 5 hours. After cooling and the addition of water, the pH is adjusted to 5 with concentrated sodium hydroxide solution. The mixture is extracted with ethyl acetate and the extract is dried over magnesium sulfate and concentrated under reduced pressure. The evaporation residue is purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate 92/8; v/v, then dichloromethane/methanol 9/1; v/v) to give the expected product in the form of a beige solid with a yield of 76%.

Provenance & Evidence