1,8-Naphthyridin-2(1H)-one

Base Information

• Chemical Name: 1,8-Naphthyridin-2(1H)-one
• CAS No.: 15936-09-1
• Molecular Formula: C₈H₆N₂O
• Molecular Weight: 146.148
• Hs Code.: 2933990090
• European Community (EC) Number: 829-657-9
• NSC Number: 172919
• DSSTox Substance ID: DTXSID90305955
• Nikkaji Number: J313.395H
• Wikidata: Q82052790
• Mol file: 15936-09-1.mol

Synonyms:1,8-naphthyridin-2(1H)-one

Chemical Property of 1,8-Naphthyridin-2(1H)-one

Chemical Property:

• Vapor Pressure: 2.4E-06mmHg at 25°C
• Melting Point: 197-199 °C(Solv: benzene (71-43-2))
• Refractive Index: 1.602
• Boiling Point: 391.8 °C at 760 mmHg
• PKA: 2.61±0.20(Predicted)
• Flash Point: 190.8 °C
• PSA: 45.75000
• Density: 1.267g/cm³
• LogP: 0.92310
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 146.048012819
• Heavy Atom Count: 11
• Complexity: 200

Purity/Quality:

97% ^*data from raw suppliers

1,8-Naphthyridin-2(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(NC(=O)C=C2)N=C1

Technology Process of 1,8-Naphthyridin-2(1H)-one

There total 16 articles about 1,8-Naphthyridin-2(1H)-one 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: 93.0%

2-<(2,2-Dimethyl-1-oxopropyl)amino>-β-hydroxy-3-pyridinepropanoic Acid, 1,1-Dimethylethyl Ester (127446-37-1) → 1,8-naphthyridine-2(1H)-one (15936-09-1)

Guidance literature:

With hydrogenchloride; for 7h; Heating;

DOI:10.1021/jo00302a049

Reference yield: 90.0%

2-chloro-1,8-naphthyridine (15936-10-4) → 2-hydroxy-1,8-naphthyridine (15936-09-1)

Guidance literature:

With hydrogenchloride; for 3h; Heating;

Reference yield: 88.0%

[1,8]naphthyridin-2-ylamine (15992-83-3) → 1,8-naphthyridine-2(1H)-one (15936-09-1)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at 20 ℃; for 0.5h;

DOI:10.1039/c7cc05449a

upstream raw materials:

2-chloro-1,8-naphthyridine

[1,8]naphthyridin-2-ylamine

2-Aminonicotinaldehyde

(E)-methyl 3-(2-aminopyridin-3-yl)acrylate

Downstream raw materials:

2-chloro-1,8-naphthyridine

2-bromo-1,8-naphthyridine

binaphthyridylamine

3,4-dihydro-1H-[1,8]naphthyridin-2-one

Refernces

7-(4-Alkylidenylpiperidinyl)-quinolone bacterial topoisomerase inhibitors

10.1016/j.bmcl.2014.10.014

The research focuses on the development of novel antibacterial fluoroquinolone agents with a 4-alkylidenylpiperidine 7-position substituent, which are effective against both quinolone-susceptible and quinolone-resistant gram-positive bacteria, including Streptococcus pneumoniae and MRSA. The study was prompted by the increasing bacterial resistance to existing quinolones, limiting their clinical use. The researchers hypothesized that a specific 2-aminoethylidenylpiperidine substituent, derived from fragment 4, would position the amino and alkyl groups similarly to the potent prema?oxacin side chain, enhancing antibacterial activity. Key chemicals involved in the synthesis included ketone 7, triethyl 2-substituted-2-phosphonoacetate 8, phthalimide, and various heterocyclic core structures related to marketed quinolones and naphthyridones. The synthesis process involved multiple steps, including Horner–Wadsworth–Emmons reactions, reductions, Mitsunobu reactions, and deprotections. The resulting compounds were tested for in vitro and in vivo efficacy, with analogs 22b, 23c, and 24 demonstrating superior activity to cipro?oxacin against resistant strains.