2-Bromopyridine → 2-(6-Dimethylaminohexyloxy)-3-picolinoylpyridine

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Reaction Steps

To a solution of 3.5 g of 2-bromopyridine in 20 ml of anhydrous ether is added dropwise 16.9 ml of n-butyllithium at -50° C. to -70° C., and the mixture is stirred for 30 minutes. To the mixture is added dropwise a solution of 4.9 g of 3-cyano-2-(6-dimethylaminohexyloxy)pyridine in 5 ml of anhydrous ether at -50° C. to -60° C. The mixture is stirred for 1 hour. Under ice-cooling, water and ethyl acetate are added thereto. After the ethyl acetate layer is dried over anhydrous magnesium sulfate, the solvent is distilled off. A dilute hydrochloric acid is added to the residue, and stirred at 40° C. for 10 minutes. After the completion of the reaction, the reaction mixture is rendered alkaline with 4N sodium hydroxide and extracted with toluene After the extract is washed with water and dried over anhydrous magnesium sulfate, the solvent is distilled off. The residue is converted into the fumarate in ethanol, and the fumarate is recrystallized from ethanol to give 2-(6-dimethylaminohexyloxy)-3-picolinoylpyridine 3/2 fumarate, m.p. 132°-134° C. (Decomposition)

Provenance & Evidence