Cyanoacetamide → 1,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile

HRID 1980333

Reaktionsgleichung

Reaktionsgleichung von HRID 1980333
CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:5](=O)[CH3:6].[C:15]([CH2:17][C:18]([NH2:20])=[O:19])#[N:16].C[O-].[Na+].C(OCC)(=O)C>CO.O>[C:15]([C:17]1[C:18](=[O:19])[NH:20][C:5]([CH3:6])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]=1)#[N:16]

Komponenten

7

Edukt 4

HCID 7898CyanoacetamideHCID 8857Ethyl AcetateHCID 14883693-Buten-2-one, 4-(dimethylamino)-3-phenyl-HCID 10942334Sodium Methoxide

Produkt 1

HCID 202311,2-Dihydro-6-methyl-2-oxo-5-phenyl-3-pyridinecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-dimethylamino-3-phenyl-3-butene-2-one (14.1 grams) and cyanoacetamide (5.9 grams) in 100 ml methanol was added to sodium methoxide (7.9 grams) in 100 ml methanol. The mixture was refluxed for 18 hours and then the crude reaction was stripped and the residue dissolved in a small amount of hot water. Acidification to pH 6-7 gave a gum-like solid which was collected by filtration. Further acidification to a lower pH gave only an oil. Trituration of the gum with ethyl acetate and chilling resulted in an off-white solid which was identified by NMR as the desired product, yield 2.8 grams, m.p. 280°-290° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 18 hours
  2. customthe crude reaction
  3. customAcidification to pH 6-7 gave a gum-like solid which
  4. filtrationwas collected by filtration
  5. customFurther acidification to a lower pH gave only an oil
  6. customresulted in an off-white solid which

Quellen und Nachweise

ORD-Eintrag
ord-3dbe249ec74b4f19be4cd54366c3d2af
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04508722

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