Methyl 4-hydroxyquinoline-6-carboxylate

Base Information

• Chemical Name: Methyl 4-hydroxyquinoline-6-carboxylate
• CAS No.: 933486-45-4
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.197
• Mol file: 933486-45-4.mol

Synonyms:methyl 4-hydroxyquinoline-6-carboxylate;933486-45-4;methyl 4-oxo-1,4-dihydroquinoline-6-carboxylate;948571-56-0;methyl 4-oxo-1H-quinoline-6-carboxylate;SCHEMBL1147523;GYUCOKUPAXSPHW-UHFFFAOYSA-N;YMB57156;MFCD18417587;MFCD19105059;AKOS027421092;SB71594;SB71597;AC-35570;CS-16091;CS-0088267;CS-0166757;D74679;E76721;methyl4-oxo-1,4-dihydroquinoline-6-carboxylate;A859827;EN300-28951243;Z1352925073;4-Oxo-1,4-dihydro-quinoline-6-carboxylic acid methyl ester;4-Oxo-1,4-dihydroquinoline-6-carboxylic acid methyl ester

Chemical Property of Methyl 4-hydroxyquinoline-6-carboxylate

Chemical Property:

• Boiling Point: 382.6±22.0 °C(Predicted)
• PKA: 3.49±0.40(Predicted)
• PSA: 59.16000
• Density: 1.327±0.06 g/cm3(Predicted)
• LogP: 1.31470
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 311

Purity/Quality:

97% ^*data from raw suppliers

Methyl4-hydroxyquinoline-6-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)NC=CC2=O

Technology Process of Methyl 4-hydroxyquinoline-6-carboxylate

There total 3 articles about Methyl 4-hydroxyquinoline-6-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:

5-(4-methoxycarbonylanilinomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (230631-82-0) → methyl 4-oxo-1,4-dihydroquinoline-6-carboxylate (933486-45-4,948571-56-0)

Guidance literature:

In diphenylether; biphenyl; at 260 ℃; for 0.0833333h;

Reference yield:

cycl-isopropylidene malonate (2033-24-1) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-hydroxyquinoline-6-carboxylate (933486-45-4,948571-56-0)

Guidance literature:

cycl-isopropylidene malonate; With orthoformic acid triethyl ester; at 145 ℃;

4-methoxycarbonyl aniline; at 50 - 145 ℃;

In diphenylether; at 250 ℃;

DOI:10.1021/jo062168u

Reference yield:

cycl-isopropylidene malonate (2033-24-1) + 4-methoxycarbonyl aniline (619-45-4) → methyl 4-oxo-1,4-dihydroquinoline-6-carboxylate (933486-45-4,948571-56-0)

Guidance literature:

cycl-isopropylidene malonate; With trimethyl orthoformate; at 110 ℃; for 2h; Inert atmosphere; Schlenk technique;

4-methoxycarbonyl aniline; at 110 ℃; for 2h; Inert atmosphere; Schlenk technique;

In diphenylether; at 250 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.2c00020

upstream raw materials:

cycl-isopropylidene malonate

4-methoxycarbonyl aniline

5-(4-methoxycarbonylanilinomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Downstream raw materials:

4-bromoquinoline-6-carboxylic acid methyl ester

methyl 3-iodo-4-oxo-1,4-dihydroquinoline-6-carboxylate