Sodium borohydride → HCID 53773077, compound

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Reaction Steps

The solution of 18.6 g of 5-(m-fluorobenzylideneamino)-pyridine-2-carboxylic acid methyl ester in 50 ml of hot dimethylformamide is added all at once to the solution of 5.0 g of sodium borohydride in 230 ml of methanol at -20° while stirring. The mixture warms to approximately 0° and after one hour the mixture is warmed to 35° for 10-15 minutes. It is cooled, one-half of the methanol is distilled off and the cold concentrate is conbined with 2 ml of acetic acid and the solution of 9 ml of 12 N hydrochloric acid in 70 ml of ice water. The clear solution, (pH=6) is cooled and stirred while additional ice and water is added to cause the solution to become faintly cloudy. The precipitate is collected and recrystallized from aqueous methanol, to yield the 5-(m-fluorobenzylamino)-pyridine-2-carboxylic acid methyl ester melting at 89°-92°.

Provenance & Evidence