ChemicalBook CAS DataBase List 6-Methoxynicotinic acid

6-Methoxynicotinic acid synthesis

13synthesis methods

Product Name:6-Methoxynicotinic acid
CAS Number:66572-55-2
Molecular formula:C7H7NO3
Molecular Weight:153.14

26218-80-4

66572-55-2

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).

26218-80-4 Synthesis

26218-80-4
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66572-55-2
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Yield: 92%

Reaction Conditions:

with sodium hydroxide;water in methanol at 70; for 1.5 h;

Steps:

A2.1
NaOH (0.36 g, 9.0 mmol) was dissolved in MeOH (5 itiL)' and water (5 mL) . Methyl 6-methoxynicotinate (1.0Og, 5.98 mmol) was added and the mixture was stirred at 70⁰C for 90 minutes. The solution was cooled and diluted with IN NaOH (25 mL) . The solution was extracted with EtOAc and the separated aqueous layer was acidified to pH 1. The aqueous layer was extracted with EtOAc (3 times) and the combined organic layers were dried and concentrated to yield 6-methoxynicotinic acid as a white solid (0.849, 92%): m/z (APCI pos) 154.1 (100%) (M+H).

References:

TAKEDA PHARMACEUTICAL COMPANY LIMITED WO2008/11131, 2008, A2 Location in patent:Page/Page column 138-139