3-Quinolinecarboxylic acid, 4-hydroxy-2-(methylthio)- synthesis
- Product Name:3-Quinolinecarboxylic acid, 4-hydroxy-2-(methylthio)-
- CAS Number:1029785-01-0
- Molecular formula:C11H9NO3S
- Molecular Weight:235.26
20856-25-1
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Yield:1029785-01-0 85%
Reaction Conditions:
Stage #1: 4-hydroxy-2-methylsulfanylquinoline-3-carboxylic acid ethyl esterwith water;sodium hydroxide for 1.5 h;Reflux;
Stage #2: with hydrogenchloride in water; pH=4;
Steps:
3
4-Hydroxy-2-methylsulfanyl-quinoline-3-carboxylic acid ethyl ester (8 g, 30 mmol) was heated under reflux in NaOH solution (10%, 100 mL) for 1.5 h. After cooling, the mixture was acidified with concentrated HCl to pH 4. The resulting solid was collected via filtration, washed with water (100 mL) and MeOH (100 mL) to give 2-methylsulfanyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (A-16) as a white solid (6 g, 85%). 1H NMR (CDCl3) δ 16.4 (br s, 1H), 11.1 (br s, 1H), 8.19 (d, J=8 Hz, 1H), 8.05 (d, J=8 Hz, 1H), 7.84 (t, J=8, 8 Hz, 1H), 7.52 (t, J=8 Hz, 1H), 2.74 (s, 3H); ESI-MS 235.9 m/z (MH+).
References:
US2012/309758,2012,A1 Location in patent:Page/Page column 62
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103-72-0
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