Ethyl 6-acetyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 6-acetyl-1,4-dihydro-4-oxoquinoline-3-carboxylate
• CAS No.: 692764-08-2
• Molecular Formula: C₁₄H₁₃NO₄
• Molecular Weight: 259.262
• DSSTox Substance ID: DTXSID401203463
• Mol file: 692764-08-2.mol

Synonyms:692764-08-2;ethyl 6-acetyl-1,4-dihydro-4-oxoquinoline-3-carboxylate;Ethyl 6-acetyl-4-oxo-1,4-dihydroquinoline-3-carboxylate;873969-87-0;ethyl 6-acetyl-4-oxo-1H-quinoline-3-carboxylate;6-Acetyl-4-hydroxy-quinoline-3-carboxylic acid ethyl ester;ethyl 6-acetyl-4-hydroxyquinoline-3-carboxylate;SCHEMBL2939048;DTXSID401203463;MFCD05744798;AKOS002250088;SB71361;BP-20247;CS-0380742;AB00682551-01;Ethyl 6-acetyl-1,4-dihydro-4-oxo-3-quinolinecarboxylate;6-Acetyl-4-hydroxyquinoline-3-carboxylic acid ethyl ester;1,4-dihydro-6-acetyl-4-oxoquinoline-3-carboxylic acid ethyl ester;6-Acetyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester

Chemical Property of Ethyl 6-acetyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 259.08445790
• Heavy Atom Count: 19
• Complexity: 441

Purity/Quality:

Ethyl 6-acetyl-1,4-dihydro-4-oxoquinoline-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=CNC2=C(C1=O)C=C(C=C2)C(=O)C

Technology Process of Ethyl 6-acetyl-1,4-dihydro-4-oxoquinoline-3-carboxylate

There total 6 articles about Ethyl 6-acetyl-1,4-dihydro-4-oxoquinoline-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: 93.0%

p-aminobenzophenone (99-92-3) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 6-acetyl-4-hydroxyquinoline-3-carboxylate (692764-08-2,873969-87-0)

Guidance literature:

p-aminobenzophenone; diethyl 2-ethoxymethylenemalonate; at 140 ℃; for 1h; Inert atmosphere;

In diphenylether; for 2h; Reflux; Inert atmosphere;

DOI:10.1021/jm300040p

Reference yield: 63.7%

p-aminobenzophenone (99-92-3) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 1,4-dihydro-6-acetyl-4-oxoquinoline-3-carboxylic acid ethyl ester (692764-08-2,873969-87-0)

Guidance literature:

p-aminobenzophenone; diethyl 2-ethoxymethylenemalonate; In ethanol; for 12h; Reflux;

With diphenylether; at 240 - 250 ℃;

DOI:10.1016/j.ejmech.2021.113913

Reference yield:

(4-nitrophenyl)ethanone (100-19-6) → 1,4-dihydro-6-acetyl-4-oxoquinoline-3-carboxylic acid ethyl ester (692764-08-2,873969-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iron; acetic acid

2.1: acetonitrile / 12 h / Reflux

2.2: 0.08 h / 245 - 250 °C

With iron; acetic acid; In acetonitrile;

DOI:10.17159/0379-4350/2018/v71a25 DOI:10.1039/c8md00480c

upstream raw materials:

2-[(4-acetyl-phenylamino)-methylene]-malonic acid diethyl ester

p-aminobenzophenone

diethyl 2-ethoxymethylenemalonate

(4-nitrophenyl)ethanone

Downstream raw materials:

6-acetyl-4-hydroxy-quinoline-3-carboxylic acid

1-(4-chloro-[6]quinolyl)-ethanone

1-4-fluorobenzyl-1,4-dihydro-6-acetyl-4-oxoquinoline-3-carboxylic acid ethyl ester