5-METHOXY-NICOTINIC ACID Chemical Properties

Melting point:

127-131°C

Boiling point:

330.9±22.0 °C(Predicted)

Density 

1.284±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

2.08±0.10(Predicted)

color 

Off-white to light grey

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

5-METHOXY-NICOTINIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-methoxynicotinic acid from methyl 5-methoxypyridine-3-carboxylate: 2 M aqueous NaOH solution (3 mL) was added to a mixed solution of THF (4 mL) and methanol (4 mL) containing methyl 5-methoxynicotinate (300 mg, 1.79 mmol). The reaction mixture was stirred at room temperature for 14 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was diluted with distilled water (20 mL) and the pH of the aqueous phase was subsequently adjusted to 6 with 2 M aqueous HCl. The aqueous phase was extracted with dichloromethane (20 mL x 3), the organic phases were combined and washed with saturated saline (10 mL x 2), dried over anhydrous sodium sulfate, and concentrated to give the title compound, 5-methoxynicotinic acid, as a white solid (230 mg, 84% yield).LC-MS analysis Results: retention time 0.36 min; m/z 154.1 [M+H]+.

References

[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3168 - 3185
[2] Patent: WO2016/34673, 2016, A1. Location in patent: Page/Page column 125-126