ethyl 6-hydroxy-2,4-diMethylnicotinate synthesis

4synthesis methods

Product Name:ethyl 6-hydroxy-2,4-diMethylnicotinate
CAS Number:36853-14-2
Molecular formula:C10H13NO3
Molecular Weight:195.22

41867-20-3
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36853-14-2
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Yield: 29%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;toluene at 115;

Steps:

1
(E) -Ethyl 3-aminobut-2-enoate (2.53 g, 19.6 mmol) in toluene (15 mL) was charged with 4N HCl (10 mL, 40 mmol) in dioxane. The mixture was stirred at 115°C overnight. The solution was cooled and the solid was filtered off washing with toluene. The filtrate was concentrated and the residue was purified by silica gel column chromatography (5% MeOH/EtOAc) to afford ethyl 2, 4-dimethyl-6-oxo-l, 6-dihydropyridine-3- carboxylate (1.11 g, 29%) as a white solid: ¹H NMR (400 MHz, CDCl₃) δ 1.37 (t, J = 6.8 Hz, 3H)/ 2.29 (s, 3H), 2.47 (s, 3H), 4.33 (q, J = 7.6, 14.4 Hz, 2H), 6.25 (s, IH); m/z (APCI pos) 196.1 (100%) (M+H) .

References:

TAKEDA PHARMACEUTICAL COMPANY LIMITED WO2008/11131, 2008, A2 Location in patent:Page/Page column 251-252