Uses
4-Benzyloxy-2(1
H)-pyridone may be used for the synthesis of novel 2-pyridone derivatives. It may be used for the alkylation of the pyridine nitrogen under mild and anhydrous conditions, via reaction with
n-Bu
4I and KOBu-
t.
General Description
N-alkylation of 4-benzyloxy-2(1
H)-pyridone with the corresponding benzyl halides has been reported.
Synthesis
General procedure for the synthesis of 4-benzyloxy-2(1H)-pyridinone from 4-benzyloxypyridine-N-oxide: 4-benzyloxypyridine-N-oxide (24.8 g, 123 mmol) was subjected to acetic anhydride (150 mL) and heated to reflux for 1.5 hours. Upon completion of the reaction, the reaction system was cooled to room temperature and subsequently concentrated under reduced pressure. The concentrated residue was dissolved in a solvent mixture of ethyl acetate (150 mL) and methanol (10 mL) and stirred at 60 °C for 2 hours. After the system was cooled to room temperature, the precipitated solid was collected by filtration to afford the crude 4-benzyloxy-2(1H)-pyridinone (8.84 g). Further concentration of the filtrate gave additional crude 4-benzyloxy-2(1H)-pyridinone (4.17 g). The two crude products were combined and purified by recrystallization using a solvent mixture of methanol and ethyl acetate to finally obtain the pure 4-benzyloxy-2(1H)-pyridinone (12.1 g, 49% yield).
References
[1] Patent: EP1741703, 2007, A1. Location in patent: Page/Page column 62-63
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 20, p. 5851 - 5856
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5310 - 5314
