Methyl Isoquinoline-4-carboxylate

Base Information

• Chemical Name: Methyl Isoquinoline-4-carboxylate
• CAS No.: 20317-40-2
• Molecular Formula: C11H9 N O2
• Molecular Weight: 187.19500
• Hs Code.: 2933499090
• European Community (EC) Number: 867-363-2
• DSSTox Substance ID: DTXSID70474052
• Nikkaji Number: J1.228.716J
• Wikidata: Q72492290
• Mol file: 20317-40-2.mol

Synonyms:Methyl Isoquinoline-4-carboxylate;20317-40-2;4-Isoquinolinecarboxylic acid, methyl ester;MFCD11111833;Methyl 4-isoquinolinecarboxylate;Methylisoquinoline-4-carboxylate;Isoquinoline-4-carboxylic acid methyl ester;SCHEMBL2201324;Methyl isoquinolin-4-carboxylate;DTXSID70474052;GOMAQBGRXCIEBF-UHFFFAOYSA-N;AKOS006308739;CS-W022889;FS-3446;4-Isoquinolinecarboxylicacid,methyl ester;SY110892;A4422;FT-0743419;EN300-79969;J-522364;Z1198315133

Chemical Property of Methyl Isoquinoline-4-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 82℃
• Boiling Point: 315.263oC at 760 mmHg
• PKA: 3.30±0.10(Predicted)
• Flash Point: 144.466oC
• PSA: 39.19000
• Density: 1.21g/cm3
• LogP: 2.02140
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 187.063328530
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

98%min ^*data from raw suppliers

MethylIsoquinoline-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl Isoquinoline-4-carboxylate

There total 11 articles about Methyl Isoquinoline-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: 91.0%

methanol (67-56-1) + 4-bromoisoquinoline (1532-97-4) + carbon monoxide (201230-82-2) → methyl isoquinoline-4-carboxylate (20317-40-2)

Guidance literature:

With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; at 70 ℃; for 24h; under 760.051 Torr;

DOI:10.1021/jo801279r

Reference yield: 86.0%

methanol (67-56-1) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline (685103-98-4) + carbon monoxide (201230-82-2) → methyl isoquinoline-4-carboxylate (20317-40-2)

Guidance literature:

With palladium diacetate; triphenylphosphine; p-benzoquinone; at 60 ℃; for 17h;

DOI:10.1016/j.tet.2015.01.008

Reference yield: 70.0%

methanol (67-56-1) + isoquinoline-4-carbonitrile (34846-65-6) → methyl isoquinoline-4-carboxylate (20317-40-2)

Guidance literature:

With sulfuric acid; for 48h; Heating;

DOI:10.1081/SCC-120027247

upstream raw materials:

4-isoquinolinecarboxylic acid

methanol

isoquinoline-4-carbonitrile

4-bromoisoquinoline

Downstream raw materials:

1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid

Refernces

• 1、 Wenkert,Dave,Gnewuch,Sprague. "General methods of synthesis of indole alkaloids. VII. Syntheses of dl-dihydrogambirtannine and Aspidosperma-Strychnos alkaloid models.". . p. 5251 - 5256. Retrieved 1968.
• 2、 Martinelli, Joseph R.,Watson, Donald A.,Freckmann, Dominique M. M.,Barder, Timothy E.,Buchwald, Stephen L.. "Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: A general system based on xantphos". supporting information; experimental part. p. 7102 - 7107. Retrieved 2009/05/09.