Acetic Acid → 1-Ethyl-3-cyano-5,6-dimethyl-2-pyridone

HRID 416568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 416568
[Na].[CH3:2][CH:3]([C:6](=O)[CH3:7])[CH:4]=O.[CH2:9]([NH:11][C:12](=[O:16])[CH2:13][C:14]#[N:15])[CH3:10].C(O)(=O)C.N1CCCCC1>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:9]([N:11]1[C:6]([CH3:7])=[C:3]([CH3:4])[CH:2]=[C:13]([C:14]#[N:15])[C:12]1=[O:16])[CH3:10]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 2703622-Cyano-N-ethylacetamideHCID 87079555CID 87079555

Produkt 1

HCID 222664831-Ethyl-3-cyano-5,6-dimethyl-2-pyridoneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

To a suspension of 2-methyl-3-oxobutanal sodium salt (3.18 g) and N-ethylcyanoacetamide (3-0003-02) (2.243 g) in DMF (20 mL) were added acetic acid (1.49 mL) and piperidine (0.40 mL) at room temperature, and the reaction mixture was refluxed with stirring in an oil bath at 135° C. for 5 h. The reaction mixture was dissolved in chloroform and water, extracted three times with chloroform, dried over magnesium sulfate, and evaporated under reduced pressure. The obtained crystal residue (4.07 g) was washed three times with n-hexane (1 mL) to give 1-ethyl-3-cyano-5,6-dimethyl-2-pyridone (3-003-03) (3.38 g, 96%) as a brown crystal.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed
  2. extractionwater, extracted three times with chloroform
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. washThe obtained crystal residue (4.07 g) was washed three times with n-hexane (1 mL)

Quellen und Nachweise

ORD-Eintrag
ord-2fa80b6da10a4e92ae41425fc35c60f0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088924B2

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