Ethyl cyanoacetate → 3,5-Bis-ethoxycarbonyl-6-methyl-2-pyridone

HRID 542529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542529
C([O:3]C(=O)CC#N)C.[CH2:9]([O:11][CH:12]=[CH:13][C:14](=O)[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:10].[K+].[Br-].[NH:24]1[CH:29]=[CH:28]C=C[C:25]1=[O:30]>CC[O-].[Na+]>[CH2:9]([O:11][C:12]([C:13]1[C:25](=[O:30])[NH:24][C:29]([CH3:28])=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:14]=1)=[O:3])[CH3:10]

Komponenten

6

Edukt 4

HCID 7764Ethyl cyanoacetateHCID 88712-PyridoneHCID 253877Potassium BromideHCID 54463595Ethyl ethoxymethyleneacetoacetate

Produkt 1

HCID 7544503,5-Bis-ethoxycarbonyl-6-methyl-2-pyridoneAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2723922Sodium ethoxideLösungsmittel

Versuchsvorschrift

Ethylcyanoacetate (2.26 g, 0.02 mol) was added to a NaOEt solution (prepared from 0.46 g of sodium metal in 50 ml EtOH), followed by compound 1 (3.72 g, 0.02 mol). The solution was refluxed for 12 hours. Shiny, light-yellow crystals precipitated out after 18 hours of standing at room temperature. After decolorizing with Nuchar activated carbon, white crystals of 3,5-bis-ethoxycarbonyl-6-methyl-2-pyridone were obtained: 1.45 g, 29% yield; mp=195°-197° C.; NMR (DMSO-d6) δ 1.1-1.5 (t, 6H), 2.6 (s, 3H), 4.1-4.5 (q, 4H), 8.6 (s, 1H), 12.6 (NH); IR (KBr) 1660 cm-1 (C=O of pyridone), 1700 cm-1 and 1720 cm-1 (C=O of ester).

Aufarbeitung

  1. temperatureThe solution was refluxed for 12 hours
  2. customShiny, light-yellow crystals precipitated out after 18 hours
  3. customof standing at room temperature
  4. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-f2363df77e4d41088fee19103f79a913
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657919

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