Ethyl 6-methoxy-2-methylquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 6-methoxy-2-methylquinoline-3-carboxylate
• CAS No.: 86210-92-6
• Molecular Formula: C14H15NO3
• Molecular Weight: 245.278
• Hs Code.: 2933499090
• European Community (EC) Number: 804-518-5
• DSSTox Substance ID: DTXSID10347175
• Wikidata: Q82120817
• ChEMBL ID: CHEMBL1471944
• Mol file: 86210-92-6.mol

Synonyms:ethyl 6-methoxy-2-methylquinoline-3-carboxylate;86210-92-6;6-Methoxy-2-methylquinoline-3-carboxylic acid ethyl ester;Oprea1_826514;MLS000528135;CHEMBL1471944;SCHEMBL23815706;6-Methoxy-2-methyl-quinoline-3-carboxylic acid ethyl ester;DTXSID10347175;HMS2170J22;HMS3310D14;MFCD01604297;STK701031;AKOS000506870;AB09291;LS-04657;SMR000120709;CS-0456530;FT-0683912;ethyl6-methoxy-2-methylquinoline-3-carboxylate;Ethyl 6-methoxy-2-methyl-3-quinolinecarboxylate #;SR-01000526936;SR-01000526936-1;Quinoline-3-carboxylic acid, 6-methoxy-2-methyl-, ethyl ester;6-Methoxy-2-methylquinoline-3-carboxylic acid ethyl ester, AldrichCPR

Chemical Property of Ethyl 6-methoxy-2-methylquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 5.2E-05mmHg at 25°C
• Boiling Point: 348°C at 760 mmHg
• Flash Point: 164.2°C
• PSA: 48.42000
• Density: 1.159g/cm³
• LogP: 2.72850
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 245.10519334
• Heavy Atom Count: 18
• Complexity: 295

Purity/Quality:

98%min ^*data from raw suppliers

6-Methoxy-2-methylquinoline-3-carboxylic acid ethyl ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N=C2C=CC(=CC2=C1)OC)C

Technology Process of Ethyl 6-methoxy-2-methylquinoline-3-carboxylate

There total 14 articles about Ethyl 6-methoxy-2-methylquinoline-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: 45.0%

ethyl acetoacetate (141-97-9) + 4-methoxy-aniline (104-94-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-methoxy-2-methylquinoline-3-carboxylic acid ethyl ester (86210-92-6)

Guidance literature:

With trichlorophosphate; for 4h; Heating;

Reference yield:

2-amino-5-methoxybenzaldehyde (26831-52-7) + ethyl acetoacetate (141-97-9) → 6-methoxy-2-methylquinoline-3-carboxylic acid ethyl ester (86210-92-6)

Guidance literature:

With sodium hydroxide; ethanol;

Reference yield:

2-Amino-5-methoxybenzoic acid (6705-03-9) → 6-methoxy-2-methylquinoline-3-carboxylic acid ethyl ester (86210-92-6)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C

2: manganese(IV) oxide / dichloromethane / 24 h / 20 °C

3: water / 48 h / 70 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/adsc.201601423

upstream raw materials:

2-amino-5-methoxybenzaldehyde

ethyl acetoacetate

4-methoxy-aniline

N,N-dimethyl-formamide

Downstream raw materials:

6-methoxy-2-methylquinoline-3-carboxylic acid

6-methoxy-2-methylquinoline-3-carboxylic acid phenylamide

Refernces

• 1、 Li, Jianjun,Fu, Yiwei,Qin, Cong,Yu, Yang,Li, Hao,Wang, Wei. "Asymmetric synthesis of isoquinolinonaphthyridines catalyzed by a chiral Br?nsted acid". supporting information. p. 6474 - 6477. Retrieved 2017/08/16.
• 2、 Adams, David,Dominguez, Jose,Russo, Vicente Lo,Rekowski, Norma Morante De. "SYNTHESIS OF SUBSTITUTED QUINOLINES BY REACTION OF THE VILSMEIER REAGENT WITH ANILINOBUTENOATES". . p. 281 - 284. Retrieved 2007/10/02.