Ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate
• CAS No.: 35975-57-6
• Molecular Formula: C12H10 Br N O3
• Molecular Weight: 296.12
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID80957402
• Wikidata: Q72457049
• Mol file: 35975-57-6.mol

Synonyms:ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate;35975-57-6;692764-07-1;ethyl 8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate;ethyl 8-bromo-4-oxo-1H-quinoline-3-carboxylate;8-Bromo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester;8-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER;CBMicro_044849;Ethyl 8-bromo-4-hydroxy-3-quinolinecarboxylate;Oprea1_619276;SCHEMBL3061001;SCHEMBL21101401;DTXSID80957402;XDDQBYKFJZYKPE-UHFFFAOYSA-N;MFCD00173380;MFCD05744797;STK089217;STK151299;TQ0116;AKOS001651929;AKOS002250069;AB04329;SB21145;SB38350;3-Carbethoxy-4-hydroxy-8-bromoquinoline;BIM-0044848.P001;BB 0222297;CS-0097051;EU-0043369;6J-016;C74849;EN300-629737;A874481;AG-670/25097014;SR-01000479812;SR-01000479812-1;ETHYL8-BROMO-4-HYDROXYQUINOLINE-3-CARBOXYLATE;ethyl8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate;Z275466096;8-Bromo-4-hydroxy-quinoline-3-carboxylic acid ethyl ester;8-Bromo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester;8-Bromo-4-hydroxyquinoline-3-carboxylic acid ethyl ester, AldrichCPR;6085-11-6

Chemical Property of Ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 2.37E-06mmHg at 25°C
• Refractive Index: 1.596
• Boiling Point: 392°Cat760mmHg
• Flash Point: 190.8°C
• PSA: 59.42000
• Density: 1.555g/cm³
• LogP: 2.87960
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 294.98441
• Heavy Atom Count: 17
• Complexity: 367

Purity/Quality:

97% ^*data from raw suppliers

Ethyl8-bromo-4-hydroxyquinoline-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CNC2=C(C1=O)C=CC=C2Br

Technology Process of Ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate

There total 12 articles about Ethyl 8-bromo-4-hydroxyquinoline-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

ethyl 4-(benzyloxy)-8-bromoquinoline-3-carboxylate → ethyl-8-bromo-4-hydroxyquinolyl-3-carboxylic acid ethyl ester (35975-57-6)

Guidance literature:

With tris(bipyridine)ruthenium(II) dichloride hexahydrate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; chemoselective reaction; Schlenk technique; Irradiation; Inert atmosphere;

DOI:10.1021/acs.joc.7b02775

Reference yield: 93.2%

diethyl 2-ethoxymethylenemalonate (87-13-8) + 2-bromoaniline (615-36-1) → ethyl-8-bromo-4-hydroxyquinolyl-3-carboxylic acid ethyl ester (35975-57-6)

Guidance literature:

diethyl 2-ethoxymethylenemalonate; 2-bromoaniline; In neat (no solvent); at 100 ℃; for 2.5h;

With diphenylether; In neat (no solvent); for 4h; Reflux;

DOI:10.1021/acs.joc.7b02775

Reference yield: 90.0%

diethyl 2-ethoxymethylenemalonate (87-13-8) + 2-bromoaniline (615-36-1) → ethyl 8-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate (692764-07-1,35975-57-6)

Guidance literature:

With methanesulfonic acid; phosphorus pentoxide; at 80 - 120 ℃; for 2h;

upstream raw materials:

diethyl 2-ethoxymethylenemalonate

2-bromoaniline

2-[(2-bromo-phenylamino)methylene]malonic acid diethyl ester

diethyl (ethoxymethylene)malonate

Downstream raw materials:

ethyl 4-chloro-8-bromo-3-quinolinecarboxylate

4-[methyl-(4-methoxy-benzenesulfonyl)-amino]-8-bromo-quinoline-3-carboxylic acid

8-bromo-4-[{[4-(2-butynyloxy)phenyl]sulfonyl} (methyl)-amino]-3-quinolinecarboxylic acid

ethyl 8-bromo-4-[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]-3-quinolinecarboxylate

Refernces

• 1、 Chen, Nan-Ying,Gu, Zi-Yu,Li, Xiao-Juan,Liao, Hao-Ran,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa,Yuan, Jing-Mei,Zhang, Guo-Hai. "3-(Benzo[: D] thiazol-2-yl)-4-aminoquinoline derivatives as novel scaffold topoisomerase i inhibitor via DNA intercalation: Design, synthesis, and antitumor activities". . p. 11203 - 11214. Retrieved 2020/07/15.
• 2、 Yao, Xia,Sun, Xiuyun,Jin, Shuyu,Yang, Ling,Xu, Hongjiang,Rao, Yu. "Discovery of 4-Aminoquinoline-3-carboxamide derivatives as potent reversible Bruton's tyrosine kinase inhibitors for the treatment of rheumatoid arthritis". . p. 6561 - 6574. Retrieved 2019/08/20.