Ethyl 1,4-dihydro-6-iodo-8-methyl-4-oxoquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 1,4-dihydro-6-iodo-8-methyl-4-oxoquinoline-3-carboxylate
• CAS No.: 951006-39-6
• Molecular Formula: C₁₃H₁₂INO₃
• Molecular Weight: 357.148
• Hs Code.: 2933499090
• Mol file: 951006-39-6.mol

Synonyms:Ethyl 1,4-dihydro-6-iodo-8-methyl-4-oxoquinoline-3-carboxylate;ethyl 6-iodo-8-Methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

Chemical Property of Ethyl 1,4-dihydro-6-iodo-8-methyl-4-oxoquinoline-3-carboxylate

Chemical Property:

• Melting Point: >300℃
• Boiling Point: 428.7±45.0 °C(Predicted)
• PKA: 0.06±0.70(Predicted)
• PSA: 59.16000
• Density: 1.680±0.06 g/cm3(Predicted)
• LogP: 2.61780
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl6-Iodo-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 6-Iodo-8-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxylate is a useful reagent for studying PDE4 inhibitors.

Technology Process of Ethyl 1,4-dihydro-6-iodo-8-methyl-4-oxoquinoline-3-carboxylate

There total 2 articles about Ethyl 1,4-dihydro-6-iodo-8-methyl-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: 100.0%

diethyl 2-(((4-iodo-2-methylphenyl)amino)methylene)malonate (951006-38-5) → ethyl 6-iodo-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (951006-39-6)

Guidance literature:

In diphenylether; at 250 ℃; for 0.75h;

DOI:10.1111/cbdd.12443

Reference yield:

4-iodo-2-methylaniline (13194-68-8) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 6-iodo-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (951006-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 h / 100 °C

2: diphenylether / 0.75 h / 250 °C

In diphenylether;

DOI:10.1111/cbdd.12443

Reference yield:

ethyl 6-iodo-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (951006-39-6) → 3-[[3-carbamoyl-4-[(3-methoxyphenyl)amino]-8-methylquinolin-6-yl]sulfonyl]benzoic acid (801311-41-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydroxide / water; ethanol / 1 h / Reflux

1.2: 20 °C

2.1: thionyl chloride; N,N-dimethyl-formamide / 2 h / 80 °C

3.1: ammonium hydroxide / 20 °C

4.1: acetonitrile / 80 °C

5.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis[2-(diphenylphosphino)phenyl] ether; potassium tert-butylate / toluene / 170 °C / Microwave irradiation

6.1: Oxone / N,N-dimethyl-formamide / 20 °C

7.1: sodium hydroxide / ethanol / 45 °C

With Oxone; ammonium hydroxide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; thionyl chloride; potassium tert-butylate; N,N-dimethyl-formamide; bis[2-(diphenylphosphino)phenyl] ether; sodium hydroxide; In ethanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1111/cbdd.12443

upstream raw materials:

diethyl 2-(((4-iodo-2-methylphenyl)amino)methylene)malonate

4-iodo-2-methylaniline

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

6-iodo-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

6-iodo-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

methyl 3-(3-carbamoyl-4-(3-methoxyphenylamino)-8-methylquinolin-6-ylthio)benzoate

methyl 3-[[3-carbamoyl-4-[(3-methoxyphenyl)amino]-8-methylquinolin-6-yl]sulfonyl]benzoate

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