7-BROMO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:7-BROMO-4-OXO-1,4-DIHYDRO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
- CAS Number:179943-57-8
- Molecular formula:C12H10BrNO3
- Molecular Weight:296.12
![2-[[(3-Bromophenyl)amino]methylene]propanedioic Acid 1,3-Diethyl Ester](/CAS/20180529/GIF/351893-47-5.gif)
351893-47-5
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Yield:179943-57-8 88%
Reaction Conditions:
in diphenylether at 235; for 1 h;Inert atmosphere;
Steps:
5.1.3. General procedure B: Synthesis of compounds 12 a-d
General procedure: The malonate derivates 11a-d were dispersed in diphenylether(1.7 mL/mmol), flushed with argon and heated to 235 °C for 1 h with aheating jacket. The reaction mixture was poured into petroleum ether,the formed precipitate was collected by filtration and washed with amixture of LP/EtOAc 1/1 to yield the desired product.5.1.3.1. Ethyl 7-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate (12a).12a (colorless solid, 5 g, 88%) was obtained from 11a (5.03 g,29 mmol) according to general procedure B; m.p. > 300 °C; 1H NMR(600 MHz, DMSO-d6) δ 1.27 (t, J=7.1 Hz, 3H), 4.21 (q, J=7.1 Hz,2H), 7.57 (dd, J=8.6, 1.9 Hz, 1H), 7.82 (d, J=1.9 Hz, 1H), 8.06 (d,J=8.6 Hz, 1H), 8.58 (s, 1H), 12.31 (s, 1H); 13C NMR (151 MHz,DMSO-d6) δ 14.8, 60.2, 110.9, 121.5, 126.2, 126.6, 128.2, 128.4, 140.5,146.0, 165.0, 173.3.
References:
Simeone;Iorio;Siebert;Rehman;Schnürch;Mihovilovic;Ernst [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 14,p. 3167 - 3178] Location in patent:supporting information
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591-19-5
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