| Identification | Back Directory | [Name]
ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE | [CAS]
206257-39-8 | [Synonyms]
EOS-60328
UKRORGSYN-BB BBV-080772
Ethyl4-chloro-6-bromoquinoline-3-carboxylate
ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE
ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE-4
Ethyl6-bromo-4-chloroquinoline-3-carboxylate,97%
6-Bromo-4-chloro-3-quinolinecarboxylic acid ethyl ester
6-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
3-Quinolinecarboxylic acid, 6-bromo-4-chloro-, ethyl ester | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C12H9BrClNO2 | [MDL Number]
MFCD00173367 | [MOL File]
206257-39-8.mol | [Molecular Weight]
314.56 |
| Chemical Properties | Back Directory | [Melting point ]
100-102° | [Boiling point ]
378.3±37.0 °C(Predicted) | [density ]
1.578 | [refractive index ]
1.632 | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
0.98±0.27(Predicted) | [Appearance]
White to off-white Solid | [Water Solubility ]
Immiscible in water. | [InChI]
InChI=1S/C12H9BrClNO2/c1-2-17-12(16)9-6-15-10-4-3-7(13)5-8(10)11(9)14/h3-6H,2H2,1H3 | [InChIKey]
YGMLKBFPHVLHGT-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC(Br)=CC=2)C(Cl)=C(C(OCC)=O)C=1 |
| Hazard Information | Back Directory | [Uses]
Ethyl 6-bromo-4-chloroquinoline-3-carboxylate is used as pharmaceutical intermediates | [Synthesis]
Ethyl 6-bromo-4-hydroxyquinoline-3-carboxylate (11 g, 37 mmol) was suspended in anhydrous dimethylformamide (148.6 mL) under nitrogen protection. Phosphoryl chloride (20.7 mL, 222 mmol, 6 equiv) was added slowly using a syringe. After addition, the reaction mixture was stirred vigorously for 3 hours at room temperature. Upon completion of the reaction, the mixture was slowly poured into ice water (1.5 L) and stirred continuously until the ice was completely melted. The precipitated solid product was collected by filtration, washed well with water until the washings were neutral, and subsequently dried under vacuum to constant weight. Ethyl 4-chloro-6-bromoquinoline-3-carboxylate (11.4 g, 94% yield) was finally obtained. Mass spectra (ESI) m/z (M + H) + 314.0, 316.0. | [References]
[1] Patent: US2012/184577, 2012, A1. Location in patent: Page/Page column 2; 3
[2] Patent: CN105859684, 2016, A. Location in patent: Paragraph 0148; 0149; 0150
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7585 - 7596
[4] RSC Advances, 2017, vol. 7, # 4, p. 2342 - 2350
[5] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 509 - 520 |
|
|