Ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate
• CAS No.: 13250-96-9
• Molecular Formula: C12H12 N2 O3
• Molecular Weight: 232.239
• European Community (EC) Number: 236-234-7,252-589-0
• DSSTox Substance ID: DTXSID00927708
• Nikkaji Number: J260.632A,J213.778J
• ChEMBL ID: CHEMBL372420
• Mol file: 13250-96-9.mol

Synonyms:13250-96-9;Ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate;35482-56-5;ethyl 7-methyl-4-oxo-1H-1,8-naphthyridine-3-carboxylate;MLS000673271;CHEMBL372420;ethyl 7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate;EINECS 236-234-7;EINECS 252-589-0;Ethyl 7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate;SMR000314512;3-Carbethoxy-7-methyl-1,8-naphthyridin-4-ol;Ethyl 4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxylate;4-hydroxy-7-methyl-[1,8]naphthyridine-3-carboxylic acid ethyl ester;7-methyl-4-oxo-1H-1,8-naphthyridine-3-carboxylic acid ethyl ester;ethyl 7-methyl-4-oxidanylidene-1H-1,8-naphthyridine-3-carboxylate;ethyl 7-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylate;Oprea1_790025;AC-907/25005202;3-Carbethoxy-4-hydroxy-7-methyl-1,8-naphthyridine;SCHEMBL1074564;BDBM52672;cid_5373687;DTXSID00927708;HMS1642E08;HMS2698E20;ethyl 1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate;STK913981;AKOS005652079;AKOS016283830;AT15944;CCG-180093;NCGC00184225-01;BS-49395;CS-0196680;3-Carbethoxy-7-methyl-1,8-naphthyrid-4-one;EN300-76960;A806446;SR-01000509833;SR-01000509833-1;Z1192338809;Ethyl 4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxylate #;4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylic acid ethyl ester;4-keto-7-methyl-1H-1,8-naphthyridine-3-carboxylic acid ethyl ester;1,4-Dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester;1,8-Naphthyridine-3-carboxylic acid, 4-hydroxy-7-methyl-, ethyl ester;1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID,1,4-DIHYDRO-7-METHYL-4-OXO-,ETHYL ESTER;7-Methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Chemical Property of Ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate

Chemical Property:

• Vapor Pressure: 6.35E-06mmHg at 25°C
• Melting Point: 272-273 °C
• Boiling Point: 378.3°C at 760 mmHg
• PKA: 2.83±0.50(Predicted)
• Flash Point: 182.6°C
• PSA: 72.31000
• Density: 1.264g/cm³
• LogP: 1.82050
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 232.08479225
• Heavy Atom Count: 17
• Complexity: 365

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl4-Hydroxy-?7-?methyl-?1,?8-?naphthyridine-?3-?carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CNC2=C(C1=O)C=CC(=N2)C
• Uses: Ethyl 4-Hydroxy-?7-?methyl-?1,?8-?naphthyridine-?3-?carboxylate is a reagent used in the synthesis of flavoquinolones which may display antibacterial activity

Technology Process of Ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate

There total 5 articles about Ethyl 4-hydroxy-7-methyl-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: 71.0%

diethyl 2-{[(6-methyl-2-pyridyl)amino]methylene}propane-1,3-dioate (13250-95-8) → ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate (13250-96-9)

Guidance literature:

In diphenylether; for 0.5h; Heating;

DOI:10.1055/s-2005-870019

Reference yield:

2-Amino-6-methylpyridine (1824-81-3) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-{[(6-methyl-2-pyridyl)amino]methylene}propane-1,3-dioate (13250-95-8) + ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate (13250-96-9)

Guidance literature:

Reference yield:

2-Amino-6-methylpyridine (1824-81-3) → ethyl 4-hydroxy-7-methyl-1,8-naphthyridine-3-carboxylate (13250-96-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / ethanol / 16 h / Heating

2: 71 percent / diphenyl ether / 0.5 h / Heating

In diphenylether; ethanol;

DOI:10.1055/s-2005-870019

upstream raw materials:

diethyl 2-{[(6-methyl-2-pyridyl)amino]methylene}propane-1,3-dioate

2-Amino-6-methylpyridine

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

nalidixic Acid

ethyl 4-chloro-7-methyl-1,8-naphthyridine-3-carboxylate

7-[trans-2-(5-nitro-furan-2-yl)-vinyl]-4-phenoxy-[1,8]naphthyridine-3-carboxylic acid ethyl ester

4-bromo-[1,8]naphthyridine

Refernces

• 1、 -. "Preparation and use of ortho-sulfonamido bicyclic heteroaryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors". . . Retrieved 2008/06/13.
• 2、 -. "Penicillins". . . Retrieved 2008/06/13.