5-(Methoxycarbonyl)pyridine-2-carboxylic acid

5-(Methoxycarbonyl)pyridine-2-carboxylic acid Property

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

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-22

HazardClass 

IRRITANT

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

5-(Methoxycarbonyl)pyridine-2-carboxylic acid Chemical Properties,Usage,Production

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