Methyl Acridine-4-carboxylate

Base Information

• Chemical Name: Methyl Acridine-4-carboxylate
• CAS No.: 188054-45-7
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.258
• DSSTox Substance ID: DTXSID50453921
• Nikkaji Number: J1.489.584A
• Wikidata: Q82275216
• Mol file: 188054-45-7.mol

Synonyms:Methyl Acridine-4-carboxylate;188054-45-7;Methylacridine-4-carboxylate;methyl 4-acridinecarboxylate;methyl acridine 4-carboxylate;SCHEMBL7030506;DTXSID50453921;GIFITRVWCNEJPG-UHFFFAOYSA-N;4-Acridinecarboxylic acid methyl ester;acridine-4-carboxylic acid methyl ester;A908339

Chemical Property of Methyl Acridine-4-carboxylate

Chemical Property:

• Boiling Point: 413.6±18.0 °C(Predicted)
• Density: 1.256±0.06 g/cm3(Predicted)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 237.078978594
• Heavy Atom Count: 18
• Complexity: 318

Purity/Quality:

99% ^*data from raw suppliers

Methylacridine-4-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC2=CC3=CC=CC=C3N=C21

Technology Process of Methyl Acridine-4-carboxylate

There total 5 articles about Methyl Acridine-4-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: 98.0%

N-(2-Formylphenyl)anthranilsaeuremethylester (188054-38-8) → 4-acridinecarboxylic acid methyl ester (188054-45-7)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 15h;

DOI:10.1016/S0040-4039(96)02396-9

Reference yield: 97.0%

→ 4-acridinecarboxylic acid methyl ester (188054-45-7)

Guidance literature:

Reference yield: 82.0%

2-carbomethoxyaniline (134-20-3) + ortho-bromobenzaldehyde (6630-33-7) → 4-acridinecarboxylic acid methyl ester (188054-45-7)

Guidance literature:

2-carbomethoxyaniline; With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium carbonate; In toluene; at 20 ℃; for 0.0833333h; Inert atmosphere;

ortho-bromobenzaldehyde; In toluene; at 80 ℃; for 12h; Inert atmosphere;

With aluminum (III) chloride; In toluene; at 80 ℃; for 12h;

DOI:10.1039/c5ob00755k

upstream raw materials:

N-(2-Formylphenyl)anthranilsaeuremethylester

methyl 2-benzoate

N-(2-Hydroxymethylphenyl)anthranilsaeuremethylester

2-carbomethoxyaniline

Downstream raw materials:

acridine-4-carboxylic acid

N-[2-(dimethylamino)ethyl]acridine-4-carboxamide

Refernces

• 1、 Wang, Ting-Jun,Chen, Wen-Wen,Li, Yi,Xu, Ming-Hua. "Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol". . p. 6580 - 6586. Retrieved 2015/06/16.
• 2、 Gamage, Swarna A.,Spicer, Julie A.,Rewcastle, Gordon W.,Denny, William A.. "A new synthesis of substituted acridine-4-carboxylic acids and the anticancer drug N-[2-dimethylamino)ethyl]acridine-4-carboxamide (DACA)". . p. 699 - 702. Retrieved 2007/10/03.