ChemicalBook CAS DataBase List 4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID synthesis

10synthesis methods

Product Name:4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID
CAS Number:13721-01-2
Molecular formula:C10H7NO3
Molecular Weight:189.17

26892-90-0 Synthesis

4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

26892-90-0
120 suppliers
$10.00/1g

4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

13721-01-2
239 suppliers
$11.00/250mg

Yield:13721-01-2 92%

Reaction Conditions:

Stage #1:ethyl 4-hydroxy-3-quinolinecarboxylate with sodium hydroxide;water for 2 h;Heating / reflux;
Stage #2: with hydrogenchloride in water; pH=4

Steps:

4-Oxo-1,4-dihydroquinoline-3-carboxylic acid
4-Oxo-1,4-dihydroquinoline-3-carboxylic acid 4-Hydroxyquinoline-3-carboxylic acid ethyl ester (15 g, 69 mmol) was suspended in sodium hydroxide solution (2N, 150 mL) and stirred for 2 h at reflux. After cooling, the mixture was filtered, and the filtrate was acidified to pH 4 with 2N HCl. The resulting precipitate was collected via filtration, washed with water and dried under vacuum to give 4-oxo-1,4-dihydroquinoline-3-carboxylic acid as a pale white solid (10.5 g, 92%). ¹H NMR (DMSO-d₆) δ 15.34 (s, 1H), 13.42 (s, 1H), 8.89 (s, 1H), 8.28 (d, J=8.0 Hz, 1H), 7.88 (m, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.60 (m, 1H).

References:

VERTEX PHARMACEUTICALS INCORPORATED US2008/90864, 2008, A1 Location in patent:Page/Page column 7

FullText