Thionyl Chloride → 2-Chloro-5-methyl-3-nitropyridine

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Reaction Steps

5 g of 2-hydroxy-5-methyl-3-nitropyridine are dissolved in 32 cm3 of thionyl chloride to which 2 cm3 of N,N-dimethylformamide have been added. The mixture is then brought to reflux for 2 hours. After removing the solvent under partial vacuum, the product is distributed between distilled water (30 cm3) and chloroform (3×100 cm3). The chloroform fractions are combined, dried over MgSO4, filtered and then concentrated under vacuum. The residue is recrystallized from ethanol/water. Yd.: 60-65%

Provenance & Evidence