6-chloroquinoline-8-carboxylic acid

6-chloroquinoline-8-carboxylic acid Property

Melting point:

220-222°C

Boiling point:

143 °C(Press: 12 Torr)

Density 

1.469±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetonitrile (Slightly), DMSO (Slightly)

form 

Solid

pka

-2.78±0.10(Predicted)

color 

Brown

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

6-chloroquinoline-8-carboxylic acid Chemical Properties,Usage,Production

Chemical Properties

Brown Solid

Uses

A 6-substituted 8-quinolinecarboxylic acid as antimicrobial and genotoxic agent.

Synthesis

General procedure for the synthesis of 6-chloroquinoline-8-carboxylic acid from glycerol and 2-amino-5-chlorobenzoic acid: 1.01 g of 2-amino-5-chlorobenzoic acid, 26.6 mg of iodine, and 0.76 g of glycerol were mixed, and the mixture was vigorously stirred. 0.44 mL of concentrated sulfuric acid was slowly added dropwise at 65 °C to 70 °C and the reaction was carried out for 30 minutes. Subsequently, the reaction temperature was raised to 140 °C and the reaction was continued for 6 hours. Upon completion of the reaction, 17 mL of water at 0 °C was added, the pH was adjusted to 6.5, the solid was collected by filtration and washed with cold water, and then dried. The dried residue was dissolved in chloroform and filtered to remove insoluble material. Activated carbon was added to the filtrate to adsorb impurities and the activated carbon was removed by filtration again. The solvent was removed by distillation and the resulting residue was recrystallized in a mixed solution of chloroform and ethyl acetate. The resulting crystals were washed with ethyl acetate and the solvent was again removed by distillation, resulting in 96.2 mg (7.9% yield) of the target product 6-chloroquinoline-8-carboxylic acid. The compound was subjected to NMR, mass spectrometry and melting point determination, confirming that its structure conforms to the general formula of 6-chloroquinoline-8-carboxylic acid.

References

[1] Patent: WO2008/59513, 2008, A2. Location in patent: Page/Page column 14
[2] Patent: US2009/171091, 2009, A1. Location in patent: Page/Page column 6
[3] Patent: JP2018/52866, 2018, A. Location in patent: Paragraph 0046