반응 #50559

반응 방정식

cyanoacetamide

sodium hydride

Ethylacetoacetate

dimethylformamide dimethyl acetal

→

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

수율 45.6%

용매

acetic acid

THF

반응 조건

후처리

1. 1
   농축The resulting reddish oil was concentrated on the rotary evaporator
2. 2
   농축the concentrate
3. 3
   workup.DISSOLUTIONthen dissolved in THF (10 ml)
4. 4
   온도The reaction mixture was heated
5. 5
   농축concentrated on the rotary evaporator
6. 6
   기타The residue was triturated with a 50:50 CH2Cl12 -H2O mixture
7. 7
   기타collected
8. 8
   기타recrystallized (EtOAC)

실험 절차

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.

출처