6-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER Chemical Properties

Melting point:

326-329°C

Boiling point:

385.5±37.0 °C(Predicted)

Density 

1.593

storage temp. 

Inert atmosphere,Room Temperature

pka

2.16±0.50(Predicted)

form 

solid

Appearance

White to light brown Solid

InChI

InChI=1S/C12H10BrNO3/c1-2-17-12(16)9-6-14-10-4-3-7(13)5-8(10)11(9)15/h3-6H,2H2,1H3,(H,14,15)

InChIKey

IVZIOBTVAJBBAS-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933499090

6-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Synthesis

The general procedure for the synthesis of ethyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate from diethyl 2-(((4-bromophenyl)amino)methylene)malonate was as follows: intermediate 3c (330 mg, 0.879 mmol) was transferred to a microwave reaction tube and dissolved in 2 mL diphenyl ether. The reaction was carried out at 250 °C with microwave radiation for 5 min. After completion of the reaction, petroleum ether was added and the precipitate precipitated was collected by filtration. The resulting product was confirmed as ethyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate in quantitative yield by 1H-NMR analysis.

References

[1] Patent: WO2009/40377, 2009, A2. Location in patent: Page/Page column 19
[2] Patent: WO2016/10869, 2016, A2. Location in patent: Page/Page column 16
[3] Patent: WO2017/11363, 2017, A1. Location in patent: Page/Page column 16
[4] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 3, p. 350 - 354
[5] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 413 - 421

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