Ethyl 2-aminoquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 2-aminoquinoline-3-carboxylate
• CAS No.: 36926-83-7
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.239
• Hs Code.: 2933499090
• NSC Number: 138303
• DSSTox Substance ID: DTXSID40300677
• Nikkaji Number: J89.140A
• Wikidata: Q82043937
• Mol file: 36926-83-7.mol

Synonyms:ethyl 2-aminoquinoline-3-carboxylate;36926-83-7;2-Amino-quinoline-3-carboxylic acid ethyl ester;MFCD01110555;3-Quinolinecarboxylic acid, 2-amino-, ethyl ester;NSC138303;2-Amino-3-quinolinecarboxylic acid ethyl ester;SCHEMBL5193947;DTXSID40300677;HMS1700E08;ethyl 2-amino-3-quinolinecarboxylate;AKOS000643682;NSC-138303;SB36864;AS-37508;SY045216;BB 0258684;CS-0308113;FT-0683247;Amino-quinoline-3-carboxylic acid ethyl ester;2-aminoquinoline-3-carboxylic acid ethyl ester;EN300-1081173;2-amino-quinoline-3-carboxylic acid ethyl ester, AldrichCPR;623162-80-1

Chemical Property of Ethyl 2-aminoquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 4.87E-05mmHg at 25°C
• Boiling Point: 348.9°C at 760 mmHg
• Flash Point: 164.8°C
• PSA: 65.21000
• Density: 1.246g/cm³
• LogP: 2.57490
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 216.089877630
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

97% ^*data from raw suppliers

ethyl2-aminoquinoline-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=CC=CC=C2N=C1N

Technology Process of Ethyl 2-aminoquinoline-3-carboxylate

There total 3 articles about Ethyl 2-aminoquinoline-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:

ethyl 3-(2-bromophenyl)-2-cyanoacrylate (59803-32-6,103457-27-8) → ethyl 2-aminoquinoline-3-carboxylate (36926-83-7) + ethyl 3-(2-aminophenyl)-2-cyanoacrylate + ethyl 3-(2-azidophenyl)-2-cyanoacrylate

Guidance literature:

With copper(l) iodide; sodium azide; L-proline; In dimethyl sulfoxide; at 80 ℃; regioselective reaction;

DOI:10.1039/c6ra03798d

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → ethyl 2-aminoquinoline-3-carboxylate (36926-83-7) + ethyl 3-(2-aminophenyl)-2-cyanoacrylate + ethyl 3-(2-azidophenyl)-2-cyanoacrylate

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / dimethyl sulfoxide / 0.5 h / 20 °C

2: sodium azide; copper(l) iodide; L-proline / dimethyl sulfoxide / 80 °C

With copper(l) iodide; sodium azide; potassium carbonate; L-proline; In dimethyl sulfoxide; 1: |Knoevenagel Condensation;

DOI:10.1039/c6ra03798d

Reference yield:

ethyl 2-cyanoacetate (105-56-6) → ethyl 2-aminoquinoline-3-carboxylate (36926-83-7) + ethyl 3-(2-aminophenyl)-2-cyanoacrylate + ethyl 3-(2-azidophenyl)-2-cyanoacrylate

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / dimethyl sulfoxide / 0.5 h / 20 °C

2: sodium azide; copper(l) iodide; L-proline / dimethyl sulfoxide / 80 °C

With copper(l) iodide; sodium azide; potassium carbonate; L-proline; In dimethyl sulfoxide; 1: |Knoevenagel Condensation;

DOI:10.1039/c6ra03798d

upstream raw materials:

ortho-bromobenzaldehyde

ethyl 3-(2-bromophenyl)-2-cyanoacrylate

ethyl 2-cyanoacetate

Downstream raw materials:

acide amino-2 quinoleine carboxylique-3

2-aminoquinoline-3-carboxylic acid anilide

amino-2 hydroxymethyl-3 quinoleine

2-benzamidoquinoline-3-carboxylic acid anilide

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