METHYL 2,4-DIOXO-4-PYRIDIN-3-YLBUTANOATE synthesis
- Product Name:METHYL 2,4-DIOXO-4-PYRIDIN-3-YLBUTANOATE
- CAS Number:23424-36-4
- Molecular formula:C10H9NO4
- Molecular Weight:207.18
Yield:23424-36-4 66.6%
Reaction Conditions:
with sodium methylate;sodium in methanol;diethyl ether; for 1 h;Cooling with ice;
Steps:
Methyl 2,4-dioxo-4-(pyridin-3- or 4-yl)butanoates (2a,b)
A solution of 3- or 4-acetylpyridine (1a,b) (10 mmole,1.21 g, 1.1 mL) and diethyl oxalate (10 mmole, 1.46 g, 1.5mL) in diethyl ether was added slowly to a cold stirred solutionof freshly prepared sodium methoxide (12 mmole, 0.28g sodium metal in 6 mL of 99.9% methanol in an ice bath).The reaction mixture was stirred for 1 h during which thesodium salt of the product was precipitated. The solid wasfiltered, washed with methanol/diethyl ether and dried. Thesodium salt was dissolved in water. The solution was acidifiedby adding 10% acetic acid to pH 3-4 and cooled to 0°Cin an ice-bath for 30 minutes. The obtained precipitate wasfiltered, washed with water, dried and crystallized from ethanol
References:
El-Hawash, Soad A.M.;Soliman, Raafat;Youssef, Amal M.;Ragab, Hanan M.A.;Elzahhar, Perihan A.S.;El-Ashmawey, Ibrahim M.;Wahab, Abeer E. Abdel;Shaat, Iman A. [Medicinal Chemistry,2014,vol. 10,# 3,p. 318 - 338]
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