8-Hydroxy-6-quinolinecarboxylic acid

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8-Hydroxy-6-quinolinecarboxylic acid Basic information
Product Name:8-Hydroxy-6-quinolinecarboxylic acid
Synonyms:8-Hydroxy-6-quinolinecarboxylic acid;8-Hydroxyquinoline-6-carboxylic acid;6-Quinolinecarboxylic acid, 8-hydroxy-;1,4-Benzenedicarbonitrile,2,10-dibromo-;1H-Benzimidazole-1-carboxylicacid,2,3-dihydro-7-oxo-,ethylester;3-Oxetanol,6-ethynyl-;8-Hydroxy-6-quinolinecarboxylic aci;Moxifloxacin Impurity 231
CAS:90800-42-3
MF:C10H7NO3
MW:189.17
EINECS:
Product Categories:
Mol File:90800-42-3.mol
8-Hydroxy-6-quinolinecarboxylic acid Structure
8-Hydroxy-6-quinolinecarboxylic acid Chemical Properties
Melting point 284 °C(Solv: acetic acid (64-19-7))
Boiling point 431.7±35.0 °C(Predicted)
density 1.480±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka2.93±0.30(Predicted)
Safety Information
MSDS Information
8-Hydroxy-6-quinolinecarboxylic acid Usage And Synthesis
Synthesis
4-Amino-3-hydroxybenzoic acid

2374-03-0

Acrolein

107-02-8

8-Hydroxy-6-quinolinecarboxylic acid

90800-42-3

General procedure for the synthesis of 8-hydroxyquinoline-6-carboxylic acid from 4-amino-3-hydroxybenzoic acid and acrolein [stabilized]: acrolein (21.8 mL, 326 mmol) was added slowly and dropwise to an aqueous 12 N solution (50 mL) containing 4-amino-3-hydroxybenzoic acid (5.00 g, 33.0 mmol). The reaction mixture was heated to reflux for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. The resulting residue was purified by reversed-phase chromatography (elution gradient: water:CH3CN 100:0 to 50:50), resulting in the target product 8-hydroxyquinoline-6-carboxylic acid (561 mg, 9% yield). The product was analyzed by UPLC/MS (ES+) and showed m/z 190.04 [M+H]+.

References[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 2, p. 521 - 533
[2] Patent: WO2015/26792, 2015, A1. Location in patent: Paragraph 0421
8-Hydroxy-6-quinolinecarboxylic acid Preparation Products And Raw materials
Raw materials4-Amino-3-hydroxybenzoic acid-->Acrolein-->Hydrochloric acid-->Water
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