ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE Chemical Properties

Melting point:

100-102°

Boiling point:

378.3±37.0 °C(Predicted)

Density 

1.578

refractive index 

1.632

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2933499090

ETHYL 6-BROMO-4-CHLORO-3-QUINOLINECARBOXYLATE Usage And Synthesis

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

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