6-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID Chemical Properties

Melting point:

271 °C (decomp)

Boiling point:

436.9±45.0 °C(Predicted)

Density 

1.862±0.06 g/cm3(Predicted)

storage temp. 

Storage temp. 2-8°C

pka

0.59±0.30(Predicted)

form 

solid

Appearance

Off-white to gray Solid

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C10H6BrNO3/c11-5-1-2-8-6(3-5)9(13)7(4-12-8)10(14)15/h1-4H,(H,12,13)(H,14,15)

InChIKey

GIUZUAUCCUFVKW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

98948-95-9

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HS Code 

2933499090

6-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID Usage And Synthesis

Uses

It is used as a pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of 4-hydroxy-6-bromoquinoline-3-carboxylic acid from ethyl 6-bromo-4-hydroxy-3-quinolinecarboxylate was as follows: ethyl 6-bromo-4-hydroxy-3-quinolinecarboxylate (102.59 g, 337.7 mmol) was suspended in a 10% aqueous potassium hydroxide solution (689 mL) and heated and refluxed for 5 hours, and the reaction solution changed to light brown. After completion of the reaction, it was cooled to room temperature and filtered to remove undissolved solid particles. The filtrate was extracted with dichloromethane to remove neutral impurities. The aqueous layer was neutralized with 3.0 N hydrochloric acid to precipitate a white precipitate. The solid was collected by filtration and washed with water. After drying in air, 4-hydroxy-6-bromoquinoline-3-carboxylic acid was obtained as 91 g (98% yield) as a white solid.EI-HRMS m/e calculated value of C10H6BrNO3 (M+) 266.9531, measured value 266.9521.

References

[1] Patent: US2006/63805, 2006, A1. Location in patent: Page/Page column 9
[2] ChemMedChem, 2015, vol. 10, # 5, p. 836 - 849
[3] Patent: CN106432073, 2017, A. Location in patent: Paragraph 0061; 0062; 0067; 0068
[4] European Journal of Medicinal Chemistry, 2015, vol. 99, p. 36 - 50
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1995, vol. 31, # 2, p. 167 - 175

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