Hydrochloric Acid → 3,4-Dichloro-2-methylpyridine

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Reaction Steps

Sodium nitrite (36 g) was added in portions to a stirred solution of 4 -amino-3 -chloro-2 -picoline (24.85 g) in conc. hydrochloric acid (750 ml) cooled to 0°-5°. After 1 hour at 0°-5 ° and a further 2 hours at room temperature the mixture was basified (NaOH), allowing the temperature to rise to ca. 50°, and extracted with ether. After drying (K2CO3 ), the extract was evaporated to dryness to give 3,4 -dichloro-2 -picoline (26.5 g) as a low melting solid.

Provenance & Evidence