Methanol → 4-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acid

HRID 2241374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241374
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][N:11]=[C:10](C#N)[C:9]2=[O:16])=[CH:4][CH:3]=1.[OH:17]S(O)(=O)=O.[CH3:22][OH:23]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:22]([OH:17])=[O:23])[C:9]2=[O:16])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 673472474-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carbonitrile

Produkt 1

HCID 673494894-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carboxylic acidAusbeute 69 %

Versuchsvorschrift

A mixture of 4-(4-fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carbonitrile (0.42 g, 1.95 mmol) and H2SO4 (4.16 mL, 78.1 mmol) was stirred at ambient temperature for 17 hours. Then the reaction mixture (amide intermediate) was added to MeOH (50 mL), and then the reaction was heated at 70° C. for 2.5 hours. The reaction mixture was quenched with ice-water and treated with aqueous 2N NaOH solution at 0° C. The mixture was acidified with aqueous 1N HCl, extracted with EtOAc, dried over MgSO4, and concentrated to afford 0.315 g of the desired product (69% for 3-step process in one pot reaction), which was rinsed with Et2O.

Aufarbeitung

  1. temperaturethe reaction was heated at 70° C. for 2.5 hours
  2. customThe reaction mixture was quenched with ice-water
  3. additiontreated with aqueous 2N NaOH solution at 0° C
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-86ef637025c3405483ed85b97ebcbf8c
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723330B2

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