Reaktion #50559

Reaktionsgleichung

cyanoacetamide

sodium hydride

Ethylacetoacetate

dimethylformamide dimethyl acetal

→

3-cyano-1,2-dihydro-6-methyl-2-oxo-5-pyridinecarboxylic acid ethyl ester

Ausbeute 45.6%

Lösungsmittel

acetic acid

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe resulting reddish oil was concentrated on the rotary evaporator
2. 2
   Einengenthe concentrate
3. 3
   workup.DISSOLUTIONthen dissolved in THF (10 ml)
4. 4
   TemperaturThe reaction mixture was heated
5. 5
   Einengenconcentrated on the rotary evaporator
6. 6
   SonstigeThe residue was triturated with a 50:50 CH2Cl12 -H2O mixture
7. 7
   Sonstigecollected
8. 8
   Sonstigerecrystallized (EtOAC)

Vorschrift

Ethylacetoacetate (6.5 g, 0.050 mole) and dimethylformamide dimethyl acetal (7.14 g, 0.060 mole) were stirred together under argon overnight. The resulting reddish oil was concentrated on the rotary evaporator and the concentrate then dissolved in THF (10 ml) and quickly added to a suspension of cyanoacetamide (4.20 g, 0.050 mole) and sodium hydride in THF (175 ml). The reaction mixture was heated and stirred overnight at 50° C. The reaction mixture was neutralized to pH 6 with acetic acid and concentrated on the rotary evaporator. The residue was triturated with a 50:50 CH2Cl12 -H2O mixture collected and recrystallized (EtOAC) giving 4.7 g of 3-cyano-1,2-dihydro-6-methyl-2-oxo-5-pyridinecarboxylic acid ethyl ester m.pt. 208°-210° C.

Quelle