2(1H)-Pyridinone, 5-acetyl- (9CI) Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

Pale yellow

Safety Information

HS Code 

2933399990

2(1H)-Pyridinone, 5-acetyl- (9CI) Usage And Synthesis

Synthesis

1. 2-Methoxy-5-acetylpyridine (1.51 g, 10 mmol) was mixed with 6 N hydrochloric acid solution and reacted at 100 °C for 5 hours. 2. After completion of the reaction, the reaction mixture was neutralized with sodium hydroxide solution to pH 7, followed by multiple extractions with dichloromethane. 3. The organic layers were combined, dried with anhydrous sodium sulfate, concentrated under reduced pressure and the residue was recrystallized by ethyl acetate to afford 5-acetyl-2(1H)-pyridinone as a white solid (1.06 g, 78% yield). 4. The above product (685.7 mg, 5 mmol) was mixed with iodobenzene (0.84 mL, 7.5 mmol), cuprous iodide (95 mg, 0.5 mmol), and potassium carbonate (691 mg, 5 mmol) in N,N-dimethylformamide (5 mL), and reacted at 135 °C overnight. 5. At the end of the reaction, the reaction mixture was diluted with 10% ammonia solution (15 mL) and extracted with ethyl acetate. 6. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 7. Purification by column chromatography (eluent: 10% ethyl acetate/dichloromethane) afforded 5-acetyl-2(1H)-pyridinone as a white solid (407 mg, 38% yield). 8. The 1H NMR spectrum of the product was consistent with the structure of target compound 16.

References

[1] Patent: WO2006/122154, 2006, A2. Location in patent: Page/Page column 64
[2] Patent: US2014/94456, 2014, A1. Location in patent: Paragraph 0558; 0560
[3] Patent: WO2015/153683, 2015, A1. Location in patent: Paragraph 0314

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