5-(Methoxycarbonyl)pyridine-2-carboxylic acid Chemical Properties

Melting point:

187 °C

Boiling point:

347.9±27.0 °C(Predicted)

Density 

1.361±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Sparingly, Heated), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.21±0.10(Predicted)

color 

White to Off-White

Stability:

Hygroscopic

InChI

InChI=1S/C8H7NO4/c1-13-8(12)5-2-3-6(7(10)11)9-4-5/h2-4H,1H3,(H,10,11)

InChIKey

NTCKZTBRFXTYBD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

17874-79-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-22

HazardClass 

IRRITANT

HS Code 

29333990

5-(Methoxycarbonyl)pyridine-2-carboxylic acid Usage And Synthesis

Chemical Properties

Off-white powder

Uses

Compound has been shown to have insulin mimetic properties.

Synthesis

The general procedure for the synthesis of 5-(methoxycarbonyl)-2-pyridinecarboxylic acid from methyl 2,5-pyridinedicarboxylate was as follows: 5-methyl 2,5-pyridinedicarboxylate (28 g, 0.146 mol) was placed in a 500 mL three-necked, round-bottomed flask assembled with a condenser and a dropping funnel with methanol (260 mL). Sodium hydroxide (6.2 g, 0.155 mol) was added slowly with stirring and the addition process lasted for 3 hours and 30 minutes. Subsequently, the reaction mixture was heated to reflux condition to form a white suspension. Under reflux conditions, 2 M hydrochloric acid solution (121 mL) was added slowly and dropwise over a period of 1 h. The reaction solution gradually changed to yellow color. Upon completion of the reaction, the flask was transferred to an ice-water bath for cooling and the solid product precipitated at room temperature. The precipitate was collected by filtration and washed sequentially with a 2:1 methanol/water mixture (35 mL) and water (50 mL). The resulting solid product was dried overnight at room temperature to yield 19.68 g (75% yield) of the target compound. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300 MHz, DMSO-d6) data: δ 9.12 (m, 1H), 8.40 (dd, J = 2.1 Hz and 8.1 Hz, 1H), 8.12 (dd, J = 0.9 Hz and 8.4 Hz, 1H), 3.89 (s, 3H). Nuclear magnetic resonance carbon (13C NMR, 75.45 MHz, DMSO-d6) data: δ 165.9, 165.0, 152.1, 150.2, 138.8, 128.3, 125.0, 53.2.

References

[1] Tetrahedron Letters, 2005, vol. 46, # 6, p. 967 - 969
[2] Organic Letters, 2004, vol. 6, # 1, p. 3 - 5
[3] European Journal of Organic Chemistry, 2010, # 1, p. 174 - 182
[4] Patent: US2007/231300, 2007, A1. Location in patent: Page/Page column 14
[5] Patent: US2008/103192, 2008, A1. Location in patent: Page/Page column 14

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