تفاعل #50559

معادلة التفاعل

cyanoacetamide

sodium hydride

Ethylacetoacetate

dimethylformamide dimethyl acetal

→

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

المردود 45.6%

المذيبات

acetic acid

THF

ظروف التفاعل

المعالجة

1. 1
   تركيزThe resulting reddish oil was concentrated on the rotary evaporator
2. 2
   تركيزthe concentrate
3. 3
   workup.DISSOLUTIONthen dissolved in THF (10 ml)
4. 4
   درجة الحرارةThe reaction mixture was heated
5. 5
   تركيزconcentrated on the rotary evaporator
6. 6
   أخرىThe residue was triturated with a 50:50 CH2Cl12 -H2O mixture
7. 7
   أخرىcollected
8. 8
   أخرىrecrystallized (EtOAC)

الإجراء التجريبي

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.

المصدر