ChemicalBook CAS DataBase List 7-hydroxyquinoline-3-carboxylic acid

7-hydroxyquinoline-3-carboxylic acid synthesis

6synthesis methods

Product Name:7-hydroxyquinoline-3-carboxylic acid
CAS Number:659730-27-5
Molecular formula:C10H7NO3
Molecular Weight:189.17

71082-46-7 Synthesis

71082-46-7
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659730-27-5
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Yield: 90%

Reaction Conditions:

with hydrogen bromide in water at 105; for 88.5 h;

Steps:

E Step E. 7-Hydroxyquinoline-3-carboxylic acid
Step E.
7-Hydroxyquinoline-3-carboxylic acid.
Ethyl 7-methoxyquinoline-3-carboxylate (7.03 g, 30.4 mmol) was dissolved in HBr (48% aq., 150 mL) and was heated at 105° C. for 88.5 h.
The reaction was cooled to ambient temperature and the precipitate was collected by filtration to afford the title compound as a brown solid (5.2 g, 90%).
¹H NMR (400 MHz, DMSO-d₆) δ 12.05-11.67 (m, 1H), 9.49 (d, J=2.0 Hz, 1H), 9.43 (s, 1H), 8.39 (d, J=9.8 Hz, 1H), 7.55-7.51 (m, 2H).
[M+H]=190.2.

References:

Basinger, Jillian;Breitenbucher, James;Freestone, Graeme;Gupta, Varsha;Kaplan, Alan;Mak, Chi-Ching;Pratt, Benjamin;Santora, Vincent;Sengupta, Dipanjan;Valdez, Lino US2014/275548, 2014, A1 Location in patent:Paragraph 0363