Water → 2-(3,5-Dichloro-6-methyl-2-oxopyrazin-1(2H)-yl)acetic acid

Ruthenium trichloride hydrate (114 mg, 0.547 mmol) was added to a stirred mixture of 1-allyl-3,5-dichloro-6-methylpyrazinone (5.45 g, 24.98 mmol) and sodium periodate (21.82 g, 0.102 mol) in water (75 ml), acetonitrile (50 ml) and carbon tetrachloride (50 ml). After 3 h the reaction mixture was extracted with methylene chloride (4 times) and the combined extracts were dried (Na2SO4) and evaporated in vacuo to a syrup. The 1H NMR (CDCl3) of this material showed it to be a 1:1 mixture of the acid and the aldehyde. The crude mixture was dissolved in acetone (50 ml) and Jones Reagent (2.7M) was added until the reaction remained orange. The reaction was then extracted into ethyl acetate which was then washed with brine, dried (Na2SO4) and evaporated in vacuo to give the title compound as a tan solid:

1. extractionAfter 3 h the reaction mixture was extracted with methylene chloride (4 times)
2. dry with materialthe combined extracts were dried (Na2SO4)
3. customevaporated in vacuo to a syrup
4. additiona 1:1 mixture of the acid
5. dissolutionThe crude mixture was dissolved in acetone (50 ml)
6. additionJones Reagent (2.7M) was added until the reaction
7. extractionThe reaction was then extracted into ethyl acetate which
8. washwas then washed with brine
9. dry with materialdried (Na2SO4)
10. customevaporated in vacuo

ORD record

ord-1d300d35deb84947a9980005988578bf

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866573