ChemicalBook > CAS DataBase List > 7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER

Product Name
7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
CAS No.
206257-41-2
Chemical Name
7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
Synonyms
Ethyl 7-broMo-4-chloroquinoline-3-carboxylate;Ethyl 4-chloro-7-broMoquinoline-3-carboxylate;7-bromo-4-chloro-3-Quinolinecarboxylic acid ethyl ester;7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER;Ethyl 7-bromo-4-chloroquinoline-3-carboxylate - [E71506];3-Quinolinecarboxylic acid, 7-bromo-4-chloro-, ethyl ester
CBNumber
CB32450002
Molecular Formula
C12H9BrClNO2
Formula Weight
314.56
MOL File
206257-41-2.mol
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7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER Property

Boiling point:
378.3±37.0 °C(Predicted)
Density 
1.578±0.06 g/cm3(Predicted)
storage temp. 
Storage temp. -20°C
pka
0.23±0.38(Predicted)
Appearance
White to off-white Solid
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
HCH0359929
Product name
7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER
Purity
95.00%
Packaging
5MG
Price
$505.53
Updated
2021/12/16
Crysdot
Product number
CD11168024
Product name
Ethyl7-bromo-4-chloroquinoline-3-carboxylate
Purity
97%
Packaging
250mg
Price
$56
Updated
2021/12/16
Chemenu
Product number
CM145738
Product name
ethyl7-bromo-4-chloroquinoline-3-carboxylate
Purity
97%
Packaging
1g
Price
$112
Updated
2021/12/16
Crysdot
Product number
CD11168024
Product name
Ethyl7-bromo-4-chloroquinoline-3-carboxylate
Purity
97%
Packaging
1g
Price
$140
Updated
2021/12/16
Abosyn
Product number
10-1865
Product name
7-Bromo-4-chloro-quinoline-3-carboxylicacidethylester
Purity
>95%
Packaging
1g
Price
$199
Updated
2021/12/16
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7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER Chemical Properties,Usage,Production

Synthesis

208580-23-8

206257-41-2

Ethyl 7-bromo-4-hydroxyquinoline-3-carboxylate (DK-I-49-1, 11.0 g, 37.1 mmol) was heated to 35-40 °C in a solvent mixture of N,N-dimethylformamide (0.1 mL, 1.3 mmol) and dichloromethane (50 mL). Oxalyl chloride (5.2 g, 40.9 mmol) was slowly added dropwise to the reaction mixture over 30 minutes. Subsequently, the reaction mixture was heated at reflux temperature (38-40 °C) for 1 hour. After completion of the reaction, the resulting brown solution was cooled to 20-25 °C. The reaction mixture was diluted with dichloromethane (150 mL) and then neutralized by slowly adding 25% aqueous potassium carbonate solution (12.5 g potassium carbonate dissolved in 50 mL of water). The organic and aqueous layers were separated and the aqueous layer was extracted with dichloromethane (50 mL). The organic layers were combined and washed with 25% aqueous potassium carbonate (12.5 g potassium carbonate dissolved in 50 mL of water). The combined organic layers were dried over magnesium sulfate. The solvent was removed by rotary evaporation and the product residue was slurried with hexane (50 mL). The solid product was filtered and washed twice with hexane (25 mL x 2). The solid was dried to afford the target product ethyl 4-chloro-7-bromoquinoline-3-carboxylate (DK-I-54-1, 7.2 g, 61% yield) as an off-white solid. The structure of the product was confirmed by 1H NMR, 13C NMR and HRMS: 1H NMR (300 MHz, DMSO) δ 9.15 (s, 1H), 8.36 (d, J = 1.9 Hz, 1H), 8.28 (d, J = 9.0 Hz, 1H), 7.98 (dd, J = 9.0, 1.9 Hz, 1H), 4.44 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz, 3H); 13C NMR (75 MHz, DMSO) δ 164.04, 151.40, 149.74, 142.34, 132.67, 131.88, 127.50, 126.64, 124.70, 123.96, 62.55, 14.46. HRMS m/z calculated for C12H10BrClNO2 (M + H)+ 313.9583, found 314.05.

References

[1] Patent: WO2016/196961, 2016, A1. Location in patent: Paragraph 00150
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2422 - 2446
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 8, p. 1487 - 1490

7-BROMO-4-CHLORO-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER Preparation Products And Raw materials

Raw materials

Preparation Products

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