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

HRID 2118

Reaktionsgleichung

Reaktionsgleichung von HRID 2118
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.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>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 7898CyanoacetamideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 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 add (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. additionwas added
  4. filtrationThe resulting yellow orange solid was filtered off
  5. washwashed several times with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3a2c011f1b3e4de5a080b95b7446e37f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728698

Verknüpfte Notizen

Wird geladen…