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5-Ethyl-2-methylpyridine

5-Ethyl-2-methylpyridine is an organic compound with the formula (C<sub>2</sub>H<sub>5</sub>)(CH<sub>3</sub>)C<sub>5</sub>H<sub>3</sub>N. One of several isomeric pyridines with this formula, this derivative is of interest because it is efficiently prepared from simple reagents and it is a convenient precursor to nicotinic acid, a form of vitamin B<sub>3</sub>. 5-Ethyl-2-methylpyridine is a colorless liquid.

Synthesis and reactions

5-Ethyl-2-methylpyridine is produced by condensation of paraldehyde (a derivative of acetaldehyde) and ammonia:

4CH<sub>3</sub>CHO + NH<sub>3</sub> → (C<sub>2</sub>H<sub>5</sub>)(CH<sub>3</sub>)C<sub>5</sub>H<sub>3</sub>N + 4H<sub>2</sub>O

The conversion is an example of a structurally complex compound efficiently made from simple precursors. Under related conditions, the condensation of acetaldehyde and ammonia delivers 2-picoline.

Oxidation of 5-ethyl-2-methylpyridine with nitric acid gives nicotinic acid via the decarboxylation of 2,5-pyridinedicarboxylic acid.

Toxicity

Like most alkylpyridines, the of 5-ethyl-2-methylpyridine is modest, being 368 mg/kg (oral, rat).

References