Реакция #50559

Уравнение реакции

cyanoacetamide

sodium hydride

Ethylacetoacetate

dimethylformamide dimethyl acetal

→

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

Выход 45.6%

Растворители

acetic acid

THF

Условия реакции

Обработка

1. 1
   КонцентрированиеThe resulting reddish oil was concentrated on the rotary evaporator
2. 2
   Концентрированиеthe concentrate
3. 3
   workup.DISSOLUTIONthen dissolved in THF (10 ml)
4. 4
   ТемператураThe reaction mixture was heated
5. 5
   Концентрированиеconcentrated on the rotary evaporator
6. 6
   ДругоеThe residue was triturated with a 50:50 CH2Cl12 -H2O mixture
7. 7
   Другоеcollected
8. 8
   Другоеrecrystallized (EtOAC)

Методика

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.

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