反応 #50559

反応方程式

cyanoacetamide

sodium hydride

Ethylacetoacetate

dimethylformamide dimethyl acetal

→

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

収率 45.6%

溶媒

acetic acid

THF

反応条件

後処理

1. 1
   濃縮The resulting reddish oil was concentrated on the rotary evaporator
2. 2
   濃縮the concentrate
3. 3
   workup.DISSOLUTIONthen dissolved in THF (10 ml)
4. 4
   温度The reaction mixture was heated
5. 5
   濃縮concentrated on the rotary evaporator
6. 6
   その他The residue was triturated with a 50:50 CH2Cl12 -H2O mixture
7. 7
   その他collected
8. 8
   その他recrystallized (EtOAC)

実験手順

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.

出典