3-(4-Methoxy-pyridin-3-yl)-propionic acid synthesis
- Product Name:3-(4-Methoxy-pyridin-3-yl)-propionic acid
- CAS Number:1171923-11-7
- Molecular formula:C9H11NO3
- Molecular Weight:181.19
1528736-55-1
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Yield:1171923-11-7 100%
Reaction Conditions:
with potassium hydroxide in methanol at 60; for 16 h;Inert atmosphere;
Steps:
3-(4-Methoxypyridin-3-yl)propionic acid (S10)
A mixture of methyl 3-(4-methoxypyridin-3-yl)propionate (212 mg, 1.09 mmol) in methanolic KOH (1.0 M, 5.5 mL, 5.5 mmol, 5 equiv) was warmed to 60 °C for 16 h. The solvent was removed and the residue was diluted with water (10 mL). The aqueous layer was washed with EtOAc (2 × 15 mL) and acidified (pH ca. 3) with 10% HCl. The aqueous phase was evaporated completely and the residue was triturated with acetone (10 mL). The solvent was decanted and evaporated to provided 196 mg (100%) of product as a tan solid: 1H NMR (DMSO-d6) δ 12.02 (broad s, 1H), 8.75 (d, 1H), 8.6 (s, 1H), 7.6 (d, 1H), 4.08 (s, 3H), 2.87 (t, 2H), 2.71 (t, 2H).
References:
Williams, John D.;Khan, Atiyya R.;Cardinale, Steven C.;Butler, Michelle M.;Bowlin, Terry L.;Peet, Norton P. [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 1,p. 419 - 434] Location in patent:supporting information
82257-15-6
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620-08-6
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