Methyl 5-hydroxynicotinate Chemical Properties

Melting point:

190 °C

Boiling point:

374.2±22.0 °C(Predicted)

Density 

1.287±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Heated, Sonicated), Methanol (Slightly, Sonicated)

pka

8.44±0.10(Predicted)

form 

Powder and Lumps

color 

Light beige

InChI

InChI=1S/C7H7NO3/c1-11-7(10)5-2-6(9)4-8-3-5/h2-4,9H,1H3

InChIKey

KJJSHOHQQHACLE-UHFFFAOYSA-N

SMILES

C1=NC=C(O)C=C1C(OC)=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-36/37/39-39-37/39

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HS Code 

29333990

Methyl 5-hydroxynicotinate Usage And Synthesis

Chemical Properties

Light beige powder and lumps

Uses

Methyl 5-Hydroxynicotinate is an intermediate used to prepare selective cyclooxygenase-2 inhibitors. It is also used to prepare imino sugars as inhibitors of liver glycogen phosphorylase.

Synthesis

Method A. Step A. Synthesis of methyl 5-hydroxynicotinate. 5-Hydroxynicotinic acid (833 g, 5.99 mol) was dissolved in methanol (6.7 L), and concentrated sulfuric acid (292 mL) was slowly added dropwise, with the rate of dropwise acceleration controlled to maintain the temperature of the reaction mixture at 30°C. After the dropwise addition, the reaction mixture was stirred under reflux conditions for 7 days. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure. Water (4 L) was added to the concentrate and the pH of the mixture was adjusted to 8 with sodium bicarbonate (NaHCO3), at which point a white solid precipitated. The mixture was stirred at room temperature for 1 h. The solid was collected by filtration and dried under vacuum at 60 °C for 3 days to afford the target product methyl 5-hydroxynicotinate (783 g, 85% yield) as a white solid. The product was characterized by 1H NMR (DMSO-d6, 400 MHz): δ 10.46 (s, 1H), 8.54 (s, 1H), 8.34-8.35 (d, J = 2.8 Hz, 1H), 7.59 (s, 1H), 3.85 (s, 3H).

References

[1] Patent: WO2015/164508, 2015, A1. Location in patent: Page/Page column 52
[2] Patent: WO2008/154563, 2008, A1. Location in patent: Page/Page column 91-92
[3] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 606 - 611
[4] Patent: WO2014/154727, 2014, A1. Location in patent: Page/Page column 43
[5] Patent: US2014/296239, 2014, A1. Location in patent: Paragraph 0114; 0115

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