2,6-Diacetylpyridine
chemical compound
2,6-Diacetylpyridine is an organic compound with the formula C5H3N(C(O)CH3)2. It is a white solid that is soluble in organic solvents. It is a disubstituted pyridine. It is a precursor to ligands in coordination chemistry.
Synthesis
The synthesis of 2,6-diacetylpyridine begins with oxidation of the methyl groups in 2,6-lutidine to form dipicolinic acid. This process has been well established with potassium permanganate and selenium dioxide. The diketone can be formed from the diester of picolinic acid groups through a Claisen condensation. The resulting adduct can be decarboxylated to give diacetylpyridine.
Treating 2,6-pyridinedicarbonitrile with methylmagnesium bromide provides an alternative synthesis for the diketone.
Precursor to Schiff base ligands
Diacetylpyridine is a popular starting material for ligands in coordination chemistry, often via template reactions.
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