Hydrochloric Acid → HCID 69102719, compound

Temperature

92.5 °C

5-Bromo-1-isopropyl-2(1H)-pyridone (50 g) was dissolved in n-butyl vinyl ether (250 ml). To the solution were added 1,3-bis(diphenylphosphino)propane (6.3 g) and powdered K2CO3 (38.2 g) and Pd(OAc)2 (1.56 g) at 25° C. The mixture was heated at 90-95° C. with stirring for 8 hours. The reaction mixture was cooled to 25-30° C. To the cooled mixture was added CHCl3 (125 ml). The precipitated salt was removed by filtration and washed with CHCl3 (125 ml). Evaporation of solvent in the filtrate in vacuo gave oily residue. The residue was dissolved in CHCl3 (125 ml). To the solution was added 1N HCl (125 ml). The reaction mixture was stirred at 25-30° C. for 1 hour. The organic layer was separated. The aqueous layer was extracted with CHCl3 (100 ml). The combined organic layer was washed with 10% aq. NaHCO3 (50 ml) and dried over MgSO4 (25 g) and silica gel (25 g). MgSO4 and silica gel were removed by filtration and washed with CHCl3. Evaporation of solvent in the filtrate in vacuo gave oily residue, which was crystallized from n-hexane (500 ml). The crystal was collected by filtration and dried in vacuo at 40° C., to give 5-acetyl-1-isopropyl-2(1H)-pyridone (32.35 g).

1. temperatureThe reaction mixture was cooled to 25-30° C
2. customThe precipitated salt was removed by filtration
3. washwashed with CHCl3 (125 ml)
4. customEvaporation of solvent in the filtrate in vacuo
5. customgave oily residue
6. stirringThe reaction mixture was stirred at 25-30° C. for 1 hour
7. customThe organic layer was separated
8. extractionThe aqueous layer was extracted with CHCl3 (100 ml)
9. washThe combined organic layer was washed with 10% aq. NaHCO3 (50 ml)
10. dry with materialdried over MgSO4 (25 g) and silica gel (25 g)
11. customMgSO4 and silica gel were removed by filtration
12. washwashed with CHCl3
13. customEvaporation of solvent in the filtrate in vacuo
14. customgave oily residue, which
15. customwas crystallized from n-hexane (500 ml)
16. filtrationThe crystal was collected by filtration
17. customdried in vacuo at 40° C.

ORD record

ord-b68a6de8c83a4f799c979a7f3f476aaf

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07407961B2