Uses
2-Methoxy-5-pyridinecarboxylic Acid is used in the synthesis of caudatin derivatives as anti-hepatitis B virus agents. In addition it can be used the synthesize potent, selective GSK-3 inhibitors for the use in the treatment of various ailments.
Synthesis
General procedure for the synthesis of 6-methoxynicotinic acid from methyl 6-methoxynicotinate: sodium hydroxide (0.36 g, 9.0 mmol) was dissolved in a solvent mixture of methanol (5 mL) and water (5 mL). To this solution was added methyl 6-methoxynicotinate (1.00 g, 5.98 mmol), followed by stirring the reaction mixture at 70 °C for 90 minutes. After completion of the reaction, the solution was cooled to room temperature and diluted with 1N sodium hydroxide solution (25 mL). The diluted solution was extracted with ethyl acetate and the aqueous layer was isolated. The aqueous layer was acidified to pH 1 with hydrochloric acid and subsequently extracted three times with ethyl acetate. All organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 6-methoxynicotinic acid as a white solid (0.849 g, 92% yield). Mass spectrometry analysis (APCI positive ion mode) showed m/z 154.1 (100%) (M + H).
References
[1] Patent: WO2008/11131, 2008, A2. Location in patent: Page/Page column 138-139
[2] Patent: EP1621537, 2006, A1. Location in patent: Page/Page column 42
[3] Patent: EP1762568, 2007, A1. Location in patent: Page/Page column 40-41
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 227 - 234
[5] Patent: US2003/100576, 2003, A1
