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4-HYDROXY-8-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ETHYL ESTER

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4-HYDROXY-8-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ETHYL ESTER Basic information

Product Name:
4-HYDROXY-8-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ETHYL ESTER
Synonyms:
  • 4-hydroxy-8-(trifluoromethyl)-3-quinolinecarboxylicacidethylester
  • 4-hydroxy-8-(trifluoromethyl)-3-quinolinecarboxylicaciethylester
  • BUTTPARK 10\01-31
  • ETHYL 4-HYDROXY-8-(TRIFLUOROMETHYL)-3-QUINOLINECARBOXYLATE
  • ETHYL 4-HYDROXY-8-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE
  • Ethyl 4-oxo-8-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxylate
  • 4-HYDROXY-8-TRIFLUOROMETHYLQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
  • 4-HYDROXY-8-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ETHYL ESTER
CAS:
23851-84-5
MF:
C13H10F3NO3
MW:
285.22
EINECS:
245-914-2
Product Categories:
  • blocks
  • Carboxes
  • Quinolines
  • Acids and Derivatives
  • Heterocycles
  • Quinoline&Isoquinoline
Mol File:
23851-84-5.mol
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4-HYDROXY-8-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ETHYL ESTER Chemical Properties

Melting point:
216 °C(Solv: ethanol (64-17-5))
Boiling point:
343.5±37.0 °C(Predicted)
Density 
1.404±0.06 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
pka
1.84±0.50(Predicted)
Appearance
White to off-white Solid
CAS DataBase Reference
23851-84-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Hazard Note 
Irritant
HS Code 
2933499090
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4-HYDROXY-8-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLIC ETHYL ESTER Usage And Synthesis

Synthesis

23779-94-4

23851-84-5

GENERAL METHOD: Diethyl [[[(trifluoromethyl)phenyl]amino}methylene]malonate (10.0 g, 0.030 mol) was mixed with Dowtherm (100 mL), heated to 250 °C and maintained at this temperature for 5 hours of reaction. Upon completion of the reaction, the mixture was cooled to 25 °C, followed by the addition of 150 mL of hexane and stirred for 10 minutes. The resulting solid product was collected by filtration and dried. The crude product was further purified by column chromatography with the eluent being a solvent mixture of petroleum ether and ethyl acetate (5:5, v/v), resulting in ethyl 4-hydroxy-8-trifluoromethylquinoline-3-carboxylate in white solid form.

References

[1] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 422 - 432
[2] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 324 - 332
[3] Patent: US2005/131014, 2005, A1. Location in patent: Page/Page column 28
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1040 - 1044
[5] Organic Process Research and Development, 2014, vol. 18, # 11, p. 1482 - 1491

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