2-CHLOROQUINOLINE-4-CARBOXYLIC ACID Chemical Properties

Melting point:

244 °C

Boiling point:

368.7±22.0 °C(Predicted)

Density 

1.469±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.17±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C10H6ClNO2/c11-9-5-7(10(13)14)6-3-1-2-4-8(6)12-9/h1-5H,(H,13,14)

InChIKey

ICNCOMYUODLTAI-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C(C(O)=O)=CC=1Cl

CAS DataBase Reference

5467-57-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933491090

2-CHLOROQUINOLINE-4-CARBOXYLIC ACID Usage And Synthesis

Uses

2-Chloroquinoline-4-carboxylic Acid is an intermediate used to prepare dimethyl(naphthalenecarbonyl)aminobenzoic acids as potent and selective EP4 antagonists.

Synthesis

The general procedure for the synthesis of 2-chloroquinoline-4-carboxylic acid from 2-quinolone-4-carboxylic acid was as follows: 2-hydroxyquinoline-4-carboxylic acid (2.57 g, 13.6 mmol) was mixed with phosphorus oxytriphosphate (POCl3, 25 mL) and heated and refluxed for 24 hours. Upon completion of the reaction, the reaction mixture was quenched by slowly pouring it into crushed ice (300 g). The precipitated solid was separated by filtration, washed thoroughly with deionized water and dried under high vacuum to give 2.47 g of white solid product in 87% yield. The product was characterized by 1H NMR (CDCl3, 300 MHz) and LCMS: 1H NMR δ 8.67 (d, 1H, J = 8.4 Hz), 7.91 (d, 1H, J = 8.1 Hz), 7.83 (s, 1H), 7.67 (t, 1H, J = 7.2 Hz), 7.54 (t, 1H, J = 7.2 Hz); LCMS (m/ z): 208 ([M+H]+).

References

[1] Patent: WO2005/30774, 2005, A1. Location in patent: Page/Page column 23
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1837,1838
[3] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1938, vol. 125, p. 60,69

2-CHLOROQUINOLINE-4-CARBOXYLIC ACID(5467-57-2)Related Product Information

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