Potassium Hydroxide → 5-{[(4-Fluorophenyl)methyl]amino}pyridine-2-carboxylic acid

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Reaction Steps

0.245 g of 5-(p-fluorobenzylamino)-pyridine-2-carboxamide are dissolved in 2.5 ml of warm n-propanol, the solution is combined with 2.5 ml of 20% aqueous potassium hydroxide and the mixture is heated on a steam bath for 16 hours. It is diluted with water and most of the n-propanol removed with a stream of nitrogen. The hot solution is filtered and the pH of the filtrate adjusted to 4 with hydrochloric acid. The precipitate formed is collected, redissolved in aqueous sodium bicarbonate, the solution filtered and reacidified with hydrochloric acid to pH=4. The solid formed is collected and air-dried, to yield the 5-(p-fluorobenzylamino)-pyridine-2-carboxylic acid melting at 196°-198°.

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