Acetonitrile → Methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 2370817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2370817
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N+:3]=1[O-:12].CC#N.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:19].C([O-])(O)=O.[Na+]>CO>[OH:12][N:3]1[C:2](=[O:19])[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4]1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 21885872methyl 6-chloronicotinate N-oxide

Produkt 1

HCID 21885934Methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a 250 mL round bottom flask containing 2-chloro-5-(methoxycarbonyl)pyridine 1-oxide (2.45 g, 13.06 mmol) was added MeCN (10 mL). The resulting mixture was stirred at 23° C. for 5 min. At this time, trifluoroacetic anhydride (20 mL) was added and the reaction was stirred 1 h. Solid NaHCO3 (25 g) was added to the flask followed by MeOH (100 mL). The solid was filtered away and the filtrate was concentrated and subjected to silica gel chromatography (80 g ISCO column, 0-5% MeOH in CHCl3) to give methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate as a yellow solid.

Aufarbeitung

  1. stirringthe reaction was stirred 1 h
  2. filtrationThe solid was filtered away
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-12c59c2cd92e48579a3884bee115853e
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710043B2

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