5-(furan-3-yl)pyridine-3-carboxylic acid synthesis

Yield:-

Reaction Conditions:

Stage #1: Methyl 5-(3-Furyl)nicotinatewith water;sodium hydroxide in methanol at 20; for 2.83333 h;
Stage #2: with citric acid in water at 20;

Steps:

23b

Reference Example 23b; A 4 mol/L aqueous solution of sodium hydroxide (2.0 mL) was added to a methanol (10 mL) solution of methyl 5-(furan-3-yl)pyridine-3-carboxylate (0.54 g) at room temperature, followed by stirring at the same temperature for 2 hours and 50 minutes. A 10% aqueous solution of citric acid (8 mL) was added to the reaction mixture at room temperature, and the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.33 g of 5-(furan-3-yl)pyridine-3-carboxylic acid as a light yellow solid.¹H-NMR (DMSO-d₆) δ: 7.13-7.17 m), 7.80-7.84 (1H, m), 8.41-8.48 (2H, m), 8.92-8.96 (1H, m), 9.05-9.11 (1H, m).

References:

US2011/275797,2011,A1 Location in patent:Page/Page column 52-53