3-phenyl-2H-2,7-naphthyridin-1-one

Base Information

• Chemical Name: 3-phenyl-2H-2,7-naphthyridin-1-one
• CAS No.: 92905-81-2
• Molecular Formula: C14H10N2O
• Molecular Weight: 222.246
• NSC Number: 79574
• DSSTox Substance ID: DTXSID60292000
• Wikidata: Q82030114
• ChEMBL ID: CHEMBL3589254
• Mol file: 92905-81-2.mol

Synonyms:3-phenyl-2,7-naphthyridin-1(2h)-one;92905-81-2;3-phenyl-2H-2,7-naphthyridin-1-one;NSC79574;NCIOpen2_004530;SCHEMBL7260213;SCHEMBL15775130;SCHEMBL15775133;DTXSID60292000;MHEBYJLLLNVBQJ-UHFFFAOYSA-N;NSC-79574;AKOS004902017;1-hydroxy-3-phenyl-2,7-naphthyridine

Chemical Property of 3-phenyl-2H-2,7-naphthyridin-1-one

Chemical Property:

• Boiling Point: 499.6°Cat760mmHg
• Flash Point: 255.9°C
• Density: 1.252g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 222.079312947
• Heavy Atom Count: 17
• Complexity: 331

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC3=C(C=NC=C3)C(=O)N2

Technology Process of 3-phenyl-2H-2,7-naphthyridin-1-one

There total 10 articles about 3-phenyl-2H-2,7-naphthyridin-1-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: 40.0%

4-(phenylethynyl)pyridine-3-carbonitrile (118159-97-0) → 3-phenyl-2,7-naphthyridin-1(2H)-one (92905-81-2)

Guidance literature:

4-(phenylethynyl)pyridine-3-carbonitrile; With sulfuric acid; In water; for 1h; Reflux;

With ammonia; In 2-methoxy-ethanol; at 100 ℃;

Reference yield:

4-bromopyridine-3-carbonitrile (154237-70-4) → 3-phenyl-2,7-naphthyridin-1(2H)-one (92905-81-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(l) iodide; sodium L-ascorbate / tetrahydrofuran / 0.5 h / 40 °C / Inert atmosphere

1.2: 10 h / 40 °C / Inert atmosphere

2.1: sulfuric acid / water / 1 h / Reflux

3.1: ammonia / 2-methoxy-ethanol / 100 °C / Sealed tube; Cooling with ice

With copper(l) iodide; sulfuric acid; ammonia; sodium L-ascorbate; In tetrahydrofuran; 2-methoxy-ethanol; water; 1.1: |Sonogashira Cross-Coupling / 1.2: |Sonogashira Cross-Coupling;

DOI:10.1016/j.bmc.2015.05.005

Reference yield:

4-bromopyridine-3-carbonitrile (154237-70-4) + phenylacetylene (536-74-3) → 3-phenyl-2,7-naphthyridin-1(2H)-one (92905-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sodium L-ascorbate / tetrahydrofuran / 0.5 h / 40 °C / Inert atmosphere

1.2: 10 h / 40 °C

2.1: sulfuric acid / water / 1 h / Reflux

2.2: 100 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; sulfuric acid; sodium L-ascorbate; triethylamine; In tetrahydrofuran; water;

upstream raw materials:

1-(2,6-dichloro-benzyl)-4-phenacylidene-1,4-dihydro-pyridine-3-carboxylic acid amide

7-benzyl-3-phenyl-2,7-naphthyridin-1(7H)-one

nicotinamide

1-benzylnicotinamide chloride