2-chloro-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide

Base Information

• Chemical Name: 2-chloro-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide
• CAS No.: 87864-14-0
• Molecular Formula: C16H20 Cl N3 O
• Molecular Weight: 305.807
• Hs Code.: 2933499090
• UNII: UN88YK33N8
• DSSTox Substance ID: DTXSID40532234
• Nikkaji Number: J28.243J
• Wikidata: Q63395742
• Mol file: 87864-14-0.mol

Synonyms:87864-14-0;2-chloro-N-[2-(diethylamino)ethyl]-4-Quinolinecarboxamide;2-chloro-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide;2-chloro-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide;UN88YK33N8;4-Quinolinecarboxamide, 2-chloro-N-[2-(diethylamino)ethyl]-;MFCD09743438;2-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)-4-QUINOLINECARBOXAMIDE;Cinchoninamide, 2-chloro-N-(2-diethylaminoethyl)-;4-Quinolinecarboxamide, 2-chloro-N-(2-(diethylamino)ethyl)-;Desbutoxy 2-Chloro Dibucaine;2-Chloro-N-(2-diethylaminoethyl)cinchoninamide;N-(2-Diethylaminoethyl)-2-chloro-4-quinolinecarboxamide;Cinchocaine Impurity A;UNII-UN88YK33N8;SCHEMBL23722839;DTXSID40532234;AKOS008947127;AC-1506;SB73078;AS-14474;Cinchocaine hydrochloride impurity A [EP];SY107528;CS-0137237;Q63395742;CINCHOCAINE HYDROCHLORIDE IMPURITY A [EP IMPURITY];2-CHLORO-N-(2-(ETHYLAMINO)ETHYL)-4-QUINOLINECARBOXAMIDE;5-Thiazolecarboxylicacid,2-[[(1,1-dimethylethoxy)carbonyl]amino]-,ethylester

Chemical Property of 2-chloro-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide

Chemical Property:

• Vapor Pressure: 5.05E-09mmHg at 25°C
• Melting Point: 65-67°C
• Boiling Point: 470.5°C at 760 mmHg
• PKA: 12.77±0.46(Predicted)
• Flash Point: 238.3°C
• PSA: 45.23000
• Density: 1.181g/cm³
• LogP: 3.35070
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 305.1294900
• Heavy Atom Count: 21
• Complexity: 336

Purity/Quality:

97% ^*data from raw suppliers

2-Chloro-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CCNC(=O)C1=CC(=NC2=CC=CC=C21)Cl
• Uses: Intermediate in the preparation of Dibucaine.

Technology Process of 2-chloro-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide

There total 6 articles about 2-chloro-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide 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: 94.0%

2-chloroquinoline-4-carbonyl chloride (2388-32-1) + N,N-diethylethylenediamine (100-36-7) → 2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) (87864-14-0)

Guidance literature:

N,N-diethylethylenediamine; With triethylamine; In dichloromethane; for 0.25h; Cooling with ice;

2-chloroquinoline-4-carbonyl chloride; In dichloromethane; at 20 ℃; Cooling with ice;

Reference yield: 82.0%

2-chloroquinoline-4-carboxylic acid (5467-57-2) + N,N-diethylethylenediamine (100-36-7) → 2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) (87864-14-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.jmedchem.9b00115

Reference yield:

2-chloroquinoline-4-carboxylic acid (5467-57-2) → 2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) (87864-14-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 4 h / 55 °C

2.1: triethylamine / dichloromethane / 0.25 h / Cooling with ice

2.2: 20 °C / Cooling with ice

With thionyl chloride; triethylamine; N,N-dimethyl-formamide; In dichloromethane;

upstream raw materials:

2-chloroquinoline-4-carbonyl chloride

N,N-diethylethylenediamine

2-hydroxyquinoline-4-carboxylic acid

2-chloroquinoline-4-carboxylic acid

Downstream raw materials:

N-[2-(diethylamino)ethyl]-2-ethoxyquinoline-4-carboxamide

Dibucaine

2-(2-methoxy-ethoxy)-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide)

N-[2-(diethylamino)ethyl]-2-(2-ethoxyethoxy)quinoline-4-carboxamide

Refernces

• 1、 Chen, Yinuo,Feng, Leilei,Jin, Mengyu,Lan, Ke,Shu, Ting,Tang, Qi,Wu, Shuwen,Xu, Zhichao,Zhang, Qiuhan,Zhou, Hai-Bing. "Identification of dibucaine derivatives as novel potent enterovirus 2C helicase inhibitors: In vitro, in vivo, and combination therapy study". . . Retrieved 2020/07/03.
• 2、 -. "Method for preparing N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide". Paragraph 0024-0029. . Retrieved 2019/03/08.