METHYL 2-HYDROXY-5-IODONICOTINATE Chemical Properties

Melting point:

199-201°

Boiling point:

362.2±42.0 °C(Predicted)

Density 

1.98±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

8.20±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

METHYL 2-HYDROXY-5-IODONICOTINATE Usage And Synthesis

Synthesis

The general procedure for the synthesis of methyl 5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylate from methyl 2-oxo-1,2-dihydro-3-pyridinecarboxylate was as follows: methyl 2-hydroxynicotinate (20 g) was dissolved in dichloromethane (500 mL) at room temperature, followed by the addition of N-iodosuccinimide (NIS, 38 g). The reaction mixture was heated to reflux for 16 hours. Upon completion of the reaction, the solvent was removed by evaporation. Ethyl acetate (200 mL) was added to the residue and heated under reflux conditions for 2 hours. The reaction mixture was cooled and the insoluble solid was collected by filtration to afford the target product methyl 2-hydroxy-5-iodonicotinate (30 g, 81% yield) as a white solid. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 3.97 (s, 3H), 8.33 (brs, 1H), 8.43 (d, J=2.4Hz, 1H).

References

[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2676 - 2688
[2] Patent: EP1477186, 2004, A1. Location in patent: Page/Page column 41
[3] Patent: EP1357111, 2003, A1. Location in patent: Page/Page column 59-60
[4] Patent: US2005/203081, 2005, A1. Location in patent: Page/Page column 13
[5] Patent: WO2008/76425, 2008, A1. Location in patent: Page/Page column 54

METHYL 2-HYDROXY-5-IODONICOTINATE(116387-40-7)Related Product Information

• 2-Hydroxy-5-iodo-3-methylpyridine
• METHYL 5-IODO-2-OXO-1-[4-(TRIFLUOROMETHYL)BENZYL]-1,2-DIHYDRO-3-PYRIDINECARBOXYLATE
• ALLYL IODIDE
• 5-IODONICOTINIC ACID
• 2-Hydroxy-5-iodopyridine
• (5-IODO-PYRIDIN-3-YL)-METHANOL
• 5-IODO-PYRIDINE-3-CARBALDEHYDE
• METHYL 2-HYDROXY-5-IODONICOTINATE