Sodium Chloride → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carbonitrile

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Reaction Steps

6.5 g (0.217 mol) of 80% strength sodium hydride in white oil are suspended in 170 ml of tetrahydrofuran and a solution of 15.3 g (0.1 mol) of 6-chloro-pyridine-3-acetonitrile in 60 ml of tetrahydrofuran is added dropwise. The mixture is stirred until completion of gas evolution, cooled and a solution of 14.3 g (0.1 mol) of 1-bromo-2-chloro-ethane in 15 ml of tetrahydrofuran are added dropwise at 5°-20° C. The mixture is stirred for 2 hours at room temperature, poured into concentrated sodium chloride solution and extracted using ether. The crude product, freed from solvent, is taken up in ethyl acetate and filtered through a bed of 200 g of silica gel. 14.3 g of a brownish, semi-crystalline material are thus obtained, which is purified by bulb tube distillation. 5.8 g (32.5% of theory) of an oil, which solidifies on cooling, are distilled at an apparatus temperature of 130°-140° C. and 0.08 mbar.

Provenance & Evidence