Ethyl Isoquinoline-1-carboxylate

Base Information

• Chemical Name: Ethyl Isoquinoline-1-carboxylate
• CAS No.: 50458-78-1
• Molecular Formula: C12H11NO2
• Molecular Weight: 201.225
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID70446052
• Nikkaji Number: J1.032.765B
• Wikidata: Q82264619
• Mol file: 50458-78-1.mol

Synonyms:Ethyl Isoquinoline-1-carboxylate;50458-78-1;ISOQUINOLINE-1-CARBOXYLIC ACID ETHYL ESTER;EthylIsoquinoline-1-carboxylate;SCHEMBL4122649;DTXSID70446052;MFCD11506154;AKOS006223058;SB37397;1-Isoquinolinecarboxylic acid ethyl ester;CS-0319963;FT-0736144

Chemical Property of Ethyl Isoquinoline-1-carboxylate

Chemical Property:

• Boiling Point: 355.5±15.0 °C(Predicted)
• PKA: 1.96±0.30(Predicted)
• PSA: 39.19000
• Density: 1.175±0.06 g/cm3(Predicted)
• LogP: 2.41150
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

Isoquinoline-1-carboxylicAcidethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NC=CC2=CC=CC=C21

Technology Process of Ethyl Isoquinoline-1-carboxylate

There total 10 articles about Ethyl Isoquinoline-1-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: 92.0%

1-isoquinolinecarboxylic acid (486-73-7) + ethanol (64-17-5) → ethyl isoquinoline-1-carboxylate (50458-78-1)

Guidance literature:

With thionyl chloride;

DOI:10.1016/j.tet.2019.05.067

Reference yield: 91.0%

Ethyl oxalyl chloride (4755-77-5) + 1-trimethylstannyl-isoquinoline (83629-90-7) → ethyl isoquinoline-1-carboxylate (50458-78-1)

Guidance literature:

In benzene; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.43.1028

Reference yield: 82.0%

ethyl 2-(methylsulfonyloxy)-2-(2-vinylphenyl)acetate (1111310-87-2) → ethyl isoquinoline-1-carboxylate (50458-78-1)

Guidance literature:

ethyl 2-(methylsulfonyloxy)-2-(2-vinylphenyl)acetate; With sodium azide; ethanol; potassium carbonate; In 1,3-dimethyl-2-imidazolidinone; at 40 ℃;

In 1,3-dimethyl-2-imidazolidinone; toluene; at 100 ℃; for 8h;

With oxygen; In 1,3-dimethyl-2-imidazolidinone; toluene; at 100 ℃;

DOI:10.1021/ol802816k

upstream raw materials:

1-isoquinolinecarboxylic acid

chloroformic acid ethyl ester

1-trimethylstannyl-isoquinoline

Ethyl oxalyl chloride

Downstream raw materials:

1-acetylisoquinoline

isoquinoline hydrazide

5-(1-isoquinolinyl)-3-phenylpyrazole

1-(1-isochinolinyl)-3-phenyl-propane-1,3-dione

Refernces

• 1、 Xie, Jian-Wei,Yao, Zhen-Bin,Wang, Xiao-Chuang,Zhang, Jie. "Cu2O/1-(2-methylhydrazine-1-carbonyl)-isoquinoline 2-oxide catalyzed C-N cross-coupling reaction in aqueous media". supporting information. p. 3788 - 3792. Retrieved 2019/06/08.
• 2、 Hui, Benjamin Wei-Qiang,Chiba, Shunsuke. "Orthogonal synthesis of isoindole and isoquinoline derivatives from organic azides". supporting information; experimental part. p. 729 - 732. Retrieved 2009/08/12.