2-(3,4-Dimethoxyphenyl)quinoline-4-carboxylic acid

Base Information

• Chemical Name: 2-(3,4-Dimethoxyphenyl)quinoline-4-carboxylic acid
• CAS No.: 133676-16-1
• Molecular Formula: C18H15NO4
• Molecular Weight: 309.321
• Hs Code.: 2933499090
• European Community (EC) Number: 673-271-1
• DSSTox Substance ID: DTXSID30350106
• Wikidata: Q82125873
• ChEMBL ID: CHEMBL2049024
• Mol file: 133676-16-1.mol

Synonyms:2-(3,4-dimethoxyphenyl)quinoline-4-carboxylic acid;133676-16-1;2-(3,4-Dimethoxy-phenyl)-quinoline-4-carboxylic acid;2-(3,4-Dimethoxyphenyl)quinoline-4-carboxylicacid;MFCD00219544;Oprea1_175304;Oprea1_655784;SCHEMBL42477;AK-968/37166244;CHEMBL2049024;DTXSID30350106;XJSXKUVHNQWOPH-UHFFFAOYSA-N;HMS1609E17;BBL012120;STK089440;AKOS000114792;CCG-105074;SB72673;WYE-175819;VS-03201;CS-0307456;FT-0608524;EN300-00813;2-(3,4-dimethoxyphenyl)-4-quinolinecarboxylicacid;SR-01000409361;4-Quinolinecarboxylicacid,2-(3,4-dimethoxyphenyl)-;SR-01000409361-1;Z56821858

Chemical Property of 2-(3,4-Dimethoxyphenyl)quinoline-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.33E-10mmHg at 25°C
• Melting Point: 232-234 °C (decomp)
• Refractive Index: 1.636
• Boiling Point: 494.6 °C at 760 mmHg
• PKA: 0.96±0.10(Predicted)
• Flash Point: 253 °C
• PSA: 68.65000
• Density: 1.275 g/cm³
• LogP: 3.61720
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 309.10010796
• Heavy Atom Count: 23
• Complexity: 416

Purity/Quality:

98%min ^*data from raw suppliers

2-(3,4-Dimethoxyphenyl)quinoline-4-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=NC3=CC=CC=C3C(=C2)C(=O)O)OC
• Uses: 2-(3,4-Dimethoxyphenyl)quinoline-4-carboxylic acid

Technology Process of 2-(3,4-Dimethoxyphenyl)quinoline-4-carboxylic acid

There total 4 articles about 2-(3,4-Dimethoxyphenyl)quinoline-4-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: 92.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → 2-(3,4-dimethoxyphenyl)quinoline-4-carboxylic acid (133676-16-1)

Guidance literature:

indole-2,3-dione; 1-(3,4-dimethoxyphenyl)ethanone; With potassium hydroxide; In ethanol; water; at 80 ℃; for 20h; Inert atmosphere;

With hydrogenchloride; In water; pH=1; Cooling with ice;

Reference yield: 26.0%

3,4-dimethoxy-benzaldehyde (120-14-9) + 2-oxo-propionic acid (127-17-3) + aniline (62-53-3) → 2-(3,4-dimethoxyphenyl)quinoline-4-carboxylic acid (133676-16-1)

Guidance literature:

3,4-dimethoxy-benzaldehyde; 2-oxo-propionic acid; In ethanol; for 0.25h; Reflux;

aniline; In ethanol; for 3h; Reflux;

DOI:10.1016/j.bioorg.2020.104373

Reference yield:

1,2-dimethoxybenzene (91-16-7) → 2-(3,4-dimethoxyphenyl)quinoline-4-carboxylic acid (133676-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: AlCl₃; nitrobenzene / -10 °C

2: ethanolic KOH

With potassium hydroxide; aluminium trichloride; nitrobenzene;

upstream raw materials:

indole-2,3-dione

1-(3,4-dimethoxyphenyl)ethanone

3,4-dimethoxy-benzaldehyde

2-oxo-propionic acid

Downstream raw materials:

C₁₈H₁₄ClNO₃

N-[2-chloro-5-(trifluoromethyl)phenyl]-2-(3,4-dimethoxyphenyl)quinoline-4-carboxamide

2-(3,4-dimethoxy-phenyl)-quinoline-4-carboxylic acid (6-fluoro-pyridin-2-yl)-amide

Refernces

• 1、 Shaikh, Sarfaraz F.,Dhavan, Pratik P.,Singh, Pinky R.,Vaidya,Jadhav,Ramana. "Synthesis of Novel Quinoline–Benzoxazolinone Ester Hybrids: In Vitro Anti-Inflammatory Activity and Antibacterial Activity". . p. 572 - 583. Retrieved 2021/05/03.
• 2、 Petrovi?, Milena M.,Roschger, Cornelia,Chaudary, Sidrah,Zierer, Andreas,Mladenovi?, Milan,Jakovljevi?, Katarina,Markovi?, Violeta,Botta, Bruno,Joksovi?, Milan D.. "Potent human dihydroorotate dehydrogenase inhibitory activity of new quinoline-4-carboxylic acids derived from phenolic aldehydes: Synthesis, cytotoxicity, lipophilicity and molecular docking studies". . . Retrieved 2020/10/21.