Toluene → 6-Fluoro-3,4-dihydro-3-oxo-2-pyrazinecarbonitrile

In a mixture of 30 mL of acetonitrile and 20 mL of water was dissolved 1.0 g of 6-fluoro-3-(4-methoxyphenoxy)-2-pyrazinecarbonitrile. After adding 11.2 g of diammonium cerium nitrate, the mixture was heated under reflux for 3 hours. The reaction mixture was returned to room temperature, a mixture consisting of 50 mL of toluene, 50 mL of water and 10 mL of 5% aqueous solution of sodium thiosulfate was added to the reaction mixture, and the aqueous layer was separated. Ethyl acetate (50 mL) was added to the aqueous layer thus obtained, and the organic layer was separated. The organic layer thus obtained was washed with saturated aqueous solution of sodium chloride, treated with active charcoal, and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Thus, 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile was obtained as a yellow-colored solid product.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 3 hours
3. customwas returned to room temperature
4. additionwas added to the reaction mixture
5. customthe aqueous layer was separated
6. additionEthyl acetate (50 mL) was added to the aqueous layer
7. customthus obtained
8. customthe organic layer was separated
9. customThe organic layer thus obtained
10. washwas washed with saturated aqueous solution of sodium chloride
11. additiontreated with active charcoal
12. dry with materialdried on anhydrous magnesium sulfate
13. customthe solvent was removed under reduced pressure

ORD record

ord-2224242be89a4dbd8bc7592b9daac680

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800629B2