Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate
• CAS No.: 5174-90-3
• Molecular Formula: C11H10 N2 O3
• Molecular Weight: 218.212
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50468671
• Wikidata: Q82295995
• Mol file: 5174-90-3.mol

Synonyms:5174-90-3;Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate;2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester;Ethyl 2-oxo-1H-1,8-naphthyridine-3-carboxylate;MFCD06659016;SCHEMBL253780;DTXSID50468671;PIHWQJBFCRABCQ-UHFFFAOYSA-N;2-HYDROXY-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER;AKOS005208191;CCG-317372;CF-0736;PB26202;SY046143;CS-0053944;FT-0677575;P10380;EN300-7364495;A828748;J-520781;ETHYL 2-HYDROXY-1,8-NAPHTHYRIDINE-3-CARBOXYLATE;F2135-0327;Ethyl 2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylate;2-Oxo-1,2-Dihydro-[1,8]naphthyridine-3-carboxylicacidethylester;2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester, AldrichCPR

Chemical Property of Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 214.8-215.0°C
• Boiling Point: 452.9°Cat760mmHg
• Flash Point: 227.7°C
• PSA: 72.31000
• Density: 1.303g/cm³
• LogP: 1.51210
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 218.06914219
• Heavy Atom Count: 16
• Complexity: 338

Purity/Quality:

98%min ^*data from raw suppliers

2-Oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(NC1=O)N=CC=C2

Technology Process of Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

There total 10 articles about Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-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: 97.0%

2-Aminonicotinaldehyde (7521-41-7) + diethyl malonate (105-53-3) → 1,8-naphthyridin-2(1H)-on-3-carboxylic acid ethyl ester (5174-90-3)

Guidance literature:

With piperidine; at 120 ℃;

DOI:10.1016/j.ejmech.2021.113895

Reference yield: 91.0%

2-Aminonicotinaldehyde (7521-41-7) + hydrogen ethyl malonate (1071-46-1) → 2-Hydroxy-1,8-naphthyridin-3-carbonsaeure-ethylester (5174-90-3)

Guidance literature:

With zirconyl chloride octahydrate; In neat (no solvent, solid phase); at 70 - 80 ℃; for 0.133333h;

Reference yield: 85.0%

2-Aminonicotinaldehyde (7521-41-7) + diethyl malonate (105-53-3) → 2-Hydroxy-1,8-naphthyridin-3-carbonsaeure-ethylester (5174-90-3)

Guidance literature:

With piperidine; at 20 ℃; for 0.25h;

upstream raw materials:

2-Aminonicotinaldehyde

diethyl malonate

hydrogen ethyl malonate

N-(3-formyl-2-pyridinyl)-2,2-dimethylpropanamide

Downstream raw materials:

N-(4-fluorophenethyl)-1,8-naphthyridin-2(1H)-on-3-carboxamide

N-cyclohexyl-1,8-naphthyridin-2(1H)-on-3-carboxamide

N-phenethyl-1,8-naphthyridin-2(1H)-on-3-carboxamide

N-(4-methylcyclohexyl)-1,8-naphthyridin-2(1H)-on-3-carboxamide

Refernces

• 1、 Bacci, Andrea,Chiarugi, Sara,Gado, Francesca,Garau, Gianpiero,Gul, Sheraz,Huguet, Samuel,Manera, Clementina,Margheritis, Eleonora,Rapposelli, Simona,Rezai, Keyvan,Riveiro, Maria E.,Runfola, Massimiliano,Sestito, Simona,Vazquez, Ramiro. "Development of potent dual PDK1/AurA kinase inhibitors for cancer therapy: Lead-optimization, structural insights, and ADME-Tox profile". supporting information. . Retrieved 2021/10/08.
• 2、 Dong, Ze,Wang, Zhen,Guo, Zhong-Qiang,Gong, Shouzhe,Zhang, Tao,Liu, Jiang,Luo, Cheng,Jiang, Hualiang,Yang, Cai-Guang. "Structure-activity relationship of spop inhibitors against kidney cancer". . p. 4849 - 4866. Retrieved 2020/06/08.