Hydrochloric Acid → 5-Acetyl-1-methylpyridin-2(1H)-one

Temperature

80 °C

5-Bromo-1-methyl-2(1H)-pyridone (150 g) was dissolved in DMF (1500 ml). To the solution were added 1,3-bis(diphenylphosphino)propane (21.7 g), n-butyl vinyl ether (400 g), and 3M aq. potassium carbonate (262.5 ml) and Pd(OAc)2 (10.2 g). The mixture was heated at 80° C. and stirred for 3 hours at the same temperature. The reaction mixture was cooled to 25-30° C. and poured to 1N HCl (1485 ml). The mixture was stirred for 2 hours at 30-40° C. The solution was extracted with EtOAc (1500 ml, three times). The aqueous layer was extracted with CH2Cl2 (1000 ml, three times). The collected organic solution was dried over MgSO4. Evaporation of solvent gave solidly residue, which was pulverized with IPA (150 ml) and IPE (1500 ml). The suspension was stood in the refrigerator overnight. The precipitate was collected by filtration, dried in vacuo, to give 5-acetyl-1-methyl-2(1H)-pyridone as white powder (128 g).

1. temperatureThe reaction mixture was cooled to 25-30° C.
2. stirringThe mixture was stirred for 2 hours at 30-40° C
3. extractionThe solution was extracted with EtOAc (1500 ml, three times)
4. extractionThe aqueous layer was extracted with CH2Cl2 (1000 ml, three times)
5. dry with materialThe collected organic solution was dried over MgSO4
6. customEvaporation of solvent
7. customgave solidly residue, which
8. customwas stood in the refrigerator overnight
9. filtrationThe precipitate was collected by filtration
10. customdried in vacuo

ORD record

ord-87529497ce7b420e808431642cf03e87

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07407961B2