Acetic Acid → 5-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1572

Reaktionsgleichung

Reaktionsgleichung von HRID 1572
C[O-].[Na+].[C:4]([CH2:6][C:7]([NH2:9])=[O:8])#[N:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[CH:20]N(C)C)[CH:18]=O)=[CH:13][CH:12]=1.C(O)(=O)C>CO.O>[C:4]([C:6]1[C:7](=[O:8])[NH:9][CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)[CH:20]=1)#[N:5]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 34489722-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehydeHCID 10942334Sodium Methoxide

Produkt 1

HCID 27639105-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone.

Aufarbeitung

  1. temperaturethe resulting suspension was refluxed overnight
  2. customDuring this time a yellow solid was formed
  3. filtrationThe resulting yellow orange solid was filtered off
  4. washwashed several times with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-506fcc7b31c241b1b92a78d6c6e2a5ef
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726176

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