Cyanoacetamide → 5-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1032991

Reaktionsgleichung

Reaktionsgleichung von HRID 1032991
[CH2:1]([CH:3]([C:6](=O)[CH3:7])[CH:4]=O)[CH3:2].[Na].[C:10]([CH2:12][C:13]([NH2:15])=[O:14])#[N:11].C([O-])(=O)C.[NH2+]1CCCCC1>O.C(O)(=O)C>[C:10]([C:12]1[C:13](=[O:14])[NH:15][C:1]([CH3:2])=[C:3]([CH2:6][CH3:7])[CH:4]=1)#[N:11]

Komponenten

7

Edukt 4

HCID 7898CyanoacetamideHCID 3014295Piperidinium acetateHCID 5360545SodiumHCID 152284102-Ethyl-3-oxobutanal

Produkt 1

HCID 102411095-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

According to the method described in J.Heterocyclic Chem., 24, 351 (1987), a mixture of 2-ethyl-3-oxobutanal, sodium salt (37.5 g, 0.275 mmol), cyanoacetamide (25.2 g, 0.30 mol), aqueous piperidinium acetate (22 mL) [prepared from glacial acetic acid (4.2 mL), water (10 mL) and piperidine (7.2 mL)] in water (775 ml) was refluxed for four hours. Glacial acetic acid (30 ml) was added cautiously (much foaming) as the product precipitated. Upon cooling to room temperature, the product was collected by filtration, washed with cold water and air dried to yield 22.3 g (50%), m.p. 237°-240° C.

Aufarbeitung

  1. temperaturewas refluxed for four hours
  2. customprecipitated
  3. filtrationthe product was collected by filtration
  4. washwashed with cold water and air
  5. customdried
  6. customto yield 22.3 g (50%), m.p. 237°-240° C.

Quellen und Nachweise

ORD-Eintrag
ord-e5332a0361704a359350e8b844c198cc
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05308854

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