Sulfuric Acid → 1-(4-Fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 2095806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095806
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[C:10]([C:17]#N)[C:9]2=[O:19])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:21].[OH-:25].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[C:10]([C:17]([OH:21])=[O:25])[C:9]2=[O:19])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 669688061-(4-Fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Produkt 1

HCID 669689221-(4-Fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 1-(4-fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile (604 mg, 2.35 mmol) and water (5 mL) was added conc. sulfuric acid (5 mL) at 0° C., and the mixture was stirred at 100° C. for 14 hr. After cooling to 0° C., the mixture was basified (pH 11) with 8N aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was acidified (pH 4) with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure to give the title compound (425 mg, 65%) as a pale-yellow solid.

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ea2fc65335a8478ca34d273fd34ecce2
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445509B2

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