2-Quinolinecarboxylic acid, 3-methyl-4-phenyl-, ethyl ester

Base Information

• Chemical Name: 2-Quinolinecarboxylic acid, 3-methyl-4-phenyl-, ethyl ester
• CAS No.: 154419-40-6
• Molecular Formula: C₁₉H₁₇NO₂
• Molecular Weight: 291.349
• DSSTox Substance ID: DTXSID401189853
• Mol file: 154419-40-6.mol

Synonyms:DTXSID401189853;NCGC00338233-01;AB01331445-02;2-Quinolinecarboxylic acid, 3-methyl-4-phenyl-, ethyl ester;154419-40-6

Chemical Property of 2-Quinolinecarboxylic acid, 3-methyl-4-phenyl-, ethyl ester

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 291.125928785
• Heavy Atom Count: 22
• Complexity: 378

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=NC2=CC=CC=C2C(=C1C)C3=CC=CC=C3

Technology Process of 2-Quinolinecarboxylic acid, 3-methyl-4-phenyl-, ethyl ester

There total 8 articles about 2-Quinolinecarboxylic acid, 3-methyl-4-phenyl-, ethyl ester 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-bromo-3-methylquinoline-2-carboxylate (1217189-30-4) + phenylboronic acid (98-80-6) → ethyl 4-phenyl-3-methylquinoline-2-carboxylate (154419-40-6)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; for 48h; Reflux; Inert atmosphere;

DOI:10.1016/j.bmcl.2009.12.061

Reference yield: 88.0%

Ethyl 2-oxobutanoate (15933-07-0) + (2-aminophenyl)(phenyl)methanone (2835-77-0) → ethyl 4-phenyl-3-methylquinoline-2-carboxylate (154419-40-6)

Guidance literature:

With chloro-trimethyl-silane; In N,N-dimethyl-formamide; at 95 ℃;

DOI:10.1055/s-2007-966003

Reference yield:

3-bromomethyl-2-ethoxycarbonyl-4-phenylquinoline (154419-41-7) → ethyl 4-phenyl-3-methylquinoline-2-carboxylate (154419-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / benzene / 6 h / Heating

2: t-BuOK / benzene / 0.5 h / Ambient temperature

3: benzene / 6 h / Heating

With potassium tert-butylate; In benzene;

DOI:10.3987/COM-93-6662

upstream raw materials:

ethanol

4-phenyl-3-methylquinoline-2-carboxylic acid

acetaldehyde

Ethyl 2-oxobutanoate

Downstream raw materials:

4-phenyl-3-methylquinoline-2-carboxylic acid

2-benzyl-9-phenyl-1,2-dihydro-3H-pyrrolo[3,4-b]quinolin-3-one

N-benzyl-3-hydroxymethyl-4-phenylquinoline-2-carboxamide

N-benzyl-3-chloromethyl-4-phenylquinoline-2-carboxamide