3-Quinolinecarboxylic acid, 4-chloro-7-nitro-, ethyl ester synthesis
- Product Name:3-Quinolinecarboxylic acid, 4-chloro-7-nitro-, ethyl ester
- CAS Number:19499-22-0
- Molecular formula:C12H9ClN2O4
- Molecular Weight:280.66
69994-70-3
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19499-22-0
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Yield:19499-22-0 37%
Reaction Conditions:
Stage #1: ethyl 7-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylatewith trichlorophosphate for 12 h;Heating / reflux;
Stage #2: with sodium hydroxide in water;
Steps:
1.3; 1
Phosphorus oxychloride (123 g, 800 mmol, 10 eq) was added to the compound 2 (20 g, 80 mmol, 1 eq) and the mixture was stirred under reflux for 12 hours . The completion of the reaction was confirmed by thin-layer chromatography. The reaction mixture was cooled, neutralized with 20% NaOH and extracted with chloroform.The extract was evaporated under reduced pressure and purified by column chromatography (ethyl acetate : hexane = 1 : 4) to obtain the target compound 3 (8.4 g, yield =37 %) .1H NMR (CDCl3, 400 MHz) δ: 9.30 (s, IH), 9.00 (s, IH), 8.59 - 8.56 (m, IH), 8.45 - 8.42 (m, IH), 4.53 (q, J = 7.2 Hz, 2H), 1.49 (t, J= 7.2 Hz, 3H). aaa
References:
WO2008/93940,2008,A1 Location in patent:Page/Page column 53; 55
