ETHYL 8-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLATE Chemical Properties

Boiling point:

385.5±37.0 °C(Predicted)

Density 

1.593±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

2.16±0.50(Predicted)

form 

solid

Appearance

Off-white to light brown Solid

InChI

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

InChIKey

XDDQBYKFJZYKPE-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

HS Code 

2933499090

ETHYL 8-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLATE Usage And Synthesis

Synthesis

The reaction was carried out with 2-bromoaniline (2.5 g, 14.62 mmol) and diethyl ethoxymethylene malonate (3.16 g, 14.62 mmol) by heating at 100 °C for 3 hours. Subsequently, the volatiles in the reaction system were removed by a stream of nitrogen. The resulting melt was slowly added to boiling diphenyl ether (10 mL) and the mixture was heated to reflux for 2 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature and petroleum ether was added to precipitate the product. The precipitated solid was collected by filtration and dried to give ethyl 4-hydroxy-8-bromoquinoline-3-carboxylate (3.5 g). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 11.65 (br s, 1H), 8.45 (s, 1H), 8.17 (d, J = 7.8 Hz, 1H), 8.05 (d, J = 7.8 Hz, 1H), 7.39-7.34 (t, J = 7.8 Hz, 1H), 4.26-4.19 (q, J = 7.2,14.1Hz, 2H), 1.30-1.26 (t, J = 6.9Hz, 3H).

References

[1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13756 - 13767
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 8, p. 1487 - 1490
[3] Patent: US2003/144507, 2003, A1
[4] Patent: EP1258252, 2002, A1
[5] Patent: US2004/18192, 2004, A1

ETHYL 8-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLATE(35975-57-6)Related Product Information

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