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98589-58-3

2,4-DIOXO-4-PYRIDIN-4-YLBUTANOIC ACID synthesis

3synthesis methods
-

Yield:-

Reaction Conditions:

with hydrogenchloride in ethanol at 70;Temperature;

Steps:

2,4-Dioxo-4-(pyridin-4-yl)butanoic Acid (7)

A mixture of methyl 2,4-dioxo-4-(pyridin-4-yl)butanoate(2b) (1 mmol, 0.207 g) and 2 N hydrochloric acid (6 mL) inethanol (5 mL) was heated at 70 °C for 3-4 h or stirred atroom temperature for 48 h. The reaction mixture was evaporatedto dryness under reduced pressure and the residuewashed with ethanol, dried and crystallized from ethanol.Yield: 73%, mp: 187-189 °C. IR (cm-1): 3350 (OH), 1714(C=O acid), 1598-1500 (C=N and C=C). 1H-NMR ( ppm):3.6-5.6 (br. s, 2H, HO-C=CH-CO, overlapped with DMSOsignal-D2O exchangeable); 8.07 (m, 2H, pyridyl-C3,5-H);8.91 (m, 2H, pyridyl-C2,6-H). MS (m/z): 193 (M+, 1.29), 78(100). Anal. Calcd. for C9H7NO4 (193.16): C, 55.96; H, 3.65;N, 7.25. Found: C, 55.63; H, 4.02; N, 7.54.

References:

Elzahhara, Perihan A.S.;Solimana, Raafat;El-Hawash, Soad A.M.;Ragaba, Hanan M.A.;Youssefa, Amal M.;Wahab, Abeer E. Abdel [Medicinal Chemistry,2015,vol. 11,# 4,p. 407 - 414]

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