2-CHLORO-3-QUINOLINECARBOXYLIC ACID Chemical Properties

Melting point:

199-240 °C

Boiling point:

363.8±27.0 °C(Predicted)

Density 

1.469±0.06 g/cm3(Predicted)

storage temp. 

Store at room temperature

pka

2.06±0.30(Predicted)

form 

solid

color 

Grey

InChI

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

InChIKey

XFSORZYTTCOBFN-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

73776-25-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933491090

2-CHLORO-3-QUINOLINECARBOXYLIC ACID Usage And Synthesis

Uses

Useful quinolinecarboxylic acid for quinoline chemistry.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 32, p. 2178, 1989 DOI: 10.1021/jm00129a026
Journal of Heterocyclic Chemistry, 26, p. 1589, 1989

Synthesis

General procedure for the synthesis of 2-chloro-3-quinolinecarboxylic acid from 2-chloro-3-quinolinecarboxaldehyde: General method: a mixed solution of 2-chloro-3-quinolinecarboxaldehyde (0.5 mmol), tert-butylhydrogen peroxide (TBHP, 4.0 eq.), and dichloroethane (DCE, 2.0 mL) was placed under aerobic environment and heated at 80°C for 6 to 8 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Water was added to the reaction mixture and extracted with ethyl acetate (EtOAc). The organic phase was washed sequentially with water and saturated saline and subsequently dried over anhydrous sodium sulfate (Na2SO4). The organic solvent was removed by concentration under reduced pressure, and the resulting crude product was purified by column chromatography (eluent ratio: hexane:ethyl acetate=15:5) to afford the target product 2-chloro-3-quinolinecarboxylic acid.

References

[1] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1019 - 1022
[2] Green Chemistry, 2012, vol. 14, # 6, p. 1649 - 1656
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10329 - 10342
[4] Australian Journal of Chemistry, 2017, vol. 70, # 10, p. 1082 - 1092
[5] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1339 - 1340

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