4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID synthesis
- Product Name:4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID
- CAS Number:34785-11-0
- Molecular formula:C10H7NO3
- Molecular Weight:189.17
26892-90-0
34785-11-0
The general procedure for the synthesis of 4-hydroxyquinoline-3-carboxylic acid from ethyl 4-hydroxyquinoline-3-carboxylate was as follows: ethyl 4-hydroxyquinoline-3-carboxylate (1.2 g, 5.5 mmol) was dissolved in 20 mL of ethanol, followed by the addition of 0.1 g/mL of aqueous sodium hydroxide (6.6 mL, 16.5 mmol). The reaction was carried out under reflux conditions for 3 hours. Upon completion of the reaction, the reaction solution was cooled to 20 °C and the pH was adjusted to 4 with 4 mol/L hydrochloric acid, at which point a solid precipitated. After recovering about 10 mL of solvent ethanol by decompression distillation, the solid was collected by filtration. The solid was washed with a mixture of ethanol and water (2 mL x 2 times) and finally dried to give 0.96 g of 4-hydroxyquinoline-3-carboxylic acid in 92% yield and the product was an off-white solid.
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Yield: 92%
Reaction Conditions:
in sodium hydroxide
Steps:
1 A-1; 4-Oxo-1,4-dihydroquinoline-3-carboxylic acid
A-1; 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 under 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 (A-1) as a pale white solid (10.5 g, 92%). 1H NMR (d-DMSO) 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 Incorported US2011/98311, 2011, A1
26892-90-0
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