7-Chloro-4-hydroxyquinoline-3-carboxylic acid

Base Information

• Chemical Name: 7-Chloro-4-hydroxyquinoline-3-carboxylic acid
• CAS No.: 86-47-5
• Molecular Formula: C10H6 Cl N O3
• Molecular Weight: 223.616
• Hs Code.: 2933499090
• European Community (EC) Number: 201-673-5
• NSC Number: 56803,27801
• UNII: 6897L5TD3T
• DSSTox Substance ID: DTXSID20235332
• Nikkaji Number: J579.565F,J90.486D
• Wikidata: Q72483495
• ChEMBL ID: CHEMBL344461
• Mol file: 86-47-5.mol

Synonyms:7-Chloro-4-hydroxyquinoline-3-carboxylic acid;86-47-5;7-Chloro-4-hydroxy-3-quinolinecarboxylic acid;7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;3-Quinolinecarboxylic acid, 7-chloro-4-hydroxy-;57278-46-3;USAF KF-16;7-chloro-4-oxo-1H-quinoline-3-carboxylic acid;Quinoline, 3-carboxy-4-hydroxy-7-chloro-;3-Carboxy-4-hydroxy-7-chloroquinoline;7-Chloro-4-Hydroxy Quinoline-3-Carboxylic acid;AI3-23857;EINECS 201-673-5;NSC 27801;BRN 0171561;CHEMBL344461;6897L5TD3T;MFCD00038080;NSC-27801;7-Chloro-4-hydroxy-quinoline-3-carboxylic acid;5-22-05-00286 (Beilstein Handbook Reference);7-chloro-4-hydroxyquinoline-3-carboxylicacid;NSC56803;26-DIIODOHYDROQUINONE;UNII-6897L5TD3T;SCHEMBL1610495;7-chloro-1,4-dihydro-4-oxo-3-Quinolinecarboxylic acid;SACLIBNEKWTDEG-UHFFFAOYSA-;DTXSID20235332;AMY14619;NSC27801;BBL027938;BDBM50404718;MFCD08235113;NSC-56803;STK653911;STK802447;AKOS000275055;AKOS005141866;CS-W013081;SB71573;7-chlor-4-hydroxyquinolin-3-carboxylsyre;AC-10982;SY033656;VS-08627;LS-141498;FT-0631406;FT-0738854;D81876;EN300-186727;W-104067;7-Chloro-4-hydroxy-3-quinolinecarboxylic acid, 97%;7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylicacid;1,4-Dihydro-7-chloro-4-oxoquinoline-3-carboxylic acid;F2137-0001

Chemical Property of 7-Chloro-4-hydroxyquinoline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 6E-07mmHg at 25°C
• Melting Point: 250 °C (dec.)(lit.)
• Refractive Index: 1.648
• Boiling Point: 395 °C at 760 mmHg
• PKA: 0.65±0.30(Predicted)
• Flash Point: 192.7 °C
• PSA: 70.42000
• Density: 1.549 g/cm³
• LogP: 2.29200
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 223.0036207
• Heavy Atom Count: 15
• Complexity: 340

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

7-Chloro-4-hydroxyquinoline-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)NC=C(C2=O)C(=O)O

Technology Process of 7-Chloro-4-hydroxyquinoline-3-carboxylic acid

There total 8 articles about 7-Chloro-4-hydroxyquinoline-3-carboxylic acid 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:

7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester (16600-22-9) → 4-hydroxy-7-chloro-3-quinoline-carboxylic acid (86-47-5)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01211a020

Reference yield:

3-chloro-aniline (108-42-9) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 4-hydroxy-7-chloro-3-quinoline-carboxylic acid (86-47-5)

Guidance literature:

In paraffin oil; at 230 ℃; for 5h; Temperature;

Reference yield:

2-(3-chlorophenylamino)methylenemalonic acid diethyl ester (3412-99-5) → 4-hydroxy-7-chloro-3-quinoline-carboxylic acid (86-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl ether / 1 h / Heating

2: 2 N aq. NaOH / 1 h / Heating

With sodium hydroxide; In diphenylether;

DOI:10.1002/jhet.5570340149

upstream raw materials:

7-chloro-4-hydroxyquinoline-3-carbonitrile

7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester

N,N'-bis-(3-chloro-phenyl)-formamidine

diethyl malonate

Downstream raw materials:

7-chloro-4-hydroxylquinoline

4,7-dichloroquinoline

Chloroquine

N-(7-chloroquinolin-4-yl)ethylenediamine

Refernces

• 1、 -. "Preparation method 4-7 -dichloroquinoline (by machine translation)". Paragraph 0023-0025; 0027-0029; 0031-0033. . Retrieved 2020/10/20.
• 2、 Chen, Shuguang,Chen, Ran,He, Meizi,Pang, Ruifang,Tan, Zhiwu,Yang, Ming. "Design, synthesis, and biological evaluation of novel quinoline derivatives as HIV-1 Tat-TAR interaction inhibitors". experimental part. p. 1948 - 1956. Retrieved 2009/05/26.