8-Bromo-4-chloroquinoline-3-carboxylic acid ethyl ester Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C12H9BrClNO2/c1-2-17-12(16)8-6-15-11-7(10(8)14)4-3-5-9(11)13/h3-6H,2H2,1H3

InChIKey

MLHAFVCMBUQWKC-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2Br)C(Cl)=C(C(OCC)=O)C=1

Safety Information

WGK Germany 

3

HS Code 

2933499090

8-Bromo-4-chloroquinoline-3-carboxylic acid ethyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 4-chloro-8-bromoquinoline-3-carboxylate from ethyl 4-hydroxy-8-bromoquinoline-3-carboxylate: ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate (2.0 g, 6.75 mmol) was dissolved in phosphorus triclosan (10 mL) and heated to reflux for 3 hr at 80 °C. Upon completion of the reaction, volatiles were removed by distillation under reduced pressure and the residue was quenched with ice water. The precipitated solid was collected by filtration and dried to give 1.8 g of the target product ethyl 4-chloro-8-bromoquinoline-3-carboxylate. The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry: 1H NMR δ 9.26 (s, 1H), 8.44-8.37 (m, 2H), 7.79-7.64 (t, J = 7.8 Hz, 1H), 4.48-4.43 (q, J = 7.2, 14.1 Hz, 2H), 1.41-1.36 (t. J = 6.9 Hz, 3H); MS (m/z): 314.01 (M + H)+.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 8, p. 1487 - 1490
[2] Patent: US2013/210844, 2013, A1. Location in patent: Paragraph 0338; 0339
[3] Patent: CN108623590, 2018, A. Location in patent: Paragraph 0149

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