2-Acetyl-6-methoxypyridine 97

Application

2-Methoxy-6-acetylpyridine exhibits relatively high chemical reactivity. The methoxy group in its structure can decompose under strong acidic conditions to yield the corresponding pyridinone compounds. The ketone carbonyl unit in its structure can also undergo bromination with brominating agents such as NBS, introducing a bromine atom onto the methyl group. Furthermore, because both the nitrogen atom and the carbonyl oxygen atom in pyridine contain lone pairs of electrons, this substance can coordinate with various metal ions, thus having certain applications in the field of fundamental research in organometallic chemistry.

Synthesis

GENERAL METHODS: A mixture of 2-methoxypyridine (1c, 0.216 mg, 2 mmol) and acetyl chloride (2a, 0.157 mg, 2 mmol) was mixed with CTAB/CTAC (0.001 mol) in 1,2-dichloroethane. The resulting reaction mixture was heated in a controlled microwave synthesizer (Biotage Initiator+ SP Wave model, 0.200 W, 2.45 GHz, with an additional 60 W at steady state) for 5 min under reaction conditions of 100 °C and 2 bar pressure. Upon completion of the reaction, the target product 2-acetyl-6-methoxypyridine (3o) was isolated by column chromatography using ethyl acetate-petroleum ether as eluent for purification on silica gel.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 26, p. 3431 - 3436