Dimethylamine → N,N-Dimethyl-2,6-pyridinediamine

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Reaction Steps

To ethanol (140 ml) saturated with dimethylamine gas at ice bath temperature is added 6-bromomethyl-2-phthalimido-pyridine (13.6 gm, 43 mmol). After stirring for 2 hours, the solution is concentrated to half volume to remove any excess dimethylamine. Hydrazine hydrate (2.4 ml) is added and refluxed for 2 hours. The reaction is cooled, filtered to remove precipitated byproduct and evaporated to dryness. The residue is dissolved in chloroform, washed with water, dried over anhydrous sodium sulfate, filtered and evaporated to give 3.8 gm of 6-dimethylamino-2-amino pyridine as an oil.

Provenance & Evidence