4-Methyl-1,8-naphthyridine

Base Information

• Chemical Name: 4-Methyl-1,8-naphthyridine
• CAS No.: 1569-17-1
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.176
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50343297
• Nikkaji Number: J101.328I
• Wikidata: Q72493291
• ChEMBL ID: CHEMBL1904411
• Mol file: 1569-17-1.mol

Synonyms:4-Methyl-1,8-naphthyridine;1569-17-1;1,8-Naphthyridine, 4-methyl-;4-methylnaphthyridine;4-Methyl-[1,8]naphthyridine;SCHEMBL3152309;CHEMBL1904411;DTXSID50343297;AMY26233;BAA56917;4-Methyl-1,8-naphthyridine, 97%;MFCD00234525;AKOS006272486;NCGC00188213-01;AS-41312;CS-0196829;FT-0744529

Chemical Property of 4-Methyl-1,8-naphthyridine

Chemical Property:

• Boiling Point: 271℃
• PKA: 4.48±0.30(Predicted)
• Flash Point: 116℃
• PSA: 25.78000
• Density: 1.141
• LogP: 1.93820
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 144.068748264
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

4-Methyl-1,8-naphthyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C=CC=NC2=NC=C1
• Uses: 4-Methyl-1,8-naphthyridine is used in the synthesis of azetidinyl ketolides for treatment of susceptible and multidrug resistant respiratory tract infections.

Technology Process of 4-Methyl-1,8-naphthyridine

There total 9 articles about 4-Methyl-1,8-naphthyridine 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: 77.0%

(E)-3-(dimethylamino)acrolein (927-63-9,692-32-0) + 2,2-Dimethyl-N-(4-methyl-2-pyridinyl)propanamide (86847-77-0) → 4-methyl[1,8]-naphthyridine (1569-17-1)

Guidance literature:

2,2-Dimethyl-N-(4-methyl-2-pyridinyl)propanamide; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - -10 ℃; for 1.5h;

(E)-3-(dimethylamino)acrolein; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h;

With hydrogenchloride; at 80 - 90 ℃; for 0.75h;

DOI:10.1055/s-2006-926229

Reference yield: 58.0%

(E)-4-(dimethylamino)but-3-en-2-one (2802-08-6) + 2-(pivaloylamino)pyridine (86847-59-8) → 4-methyl[1,8]-naphthyridine (1569-17-1) + 2-methyl-[1,8]naphthyridine (1569-16-0)

Guidance literature:

2-(pivaloylamino)pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 3h;

(E)-4-(dimethylamino)but-3-en-2-one; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h;

With hydrogenchloride; for 4h; Heating;

DOI:10.1055/s-2006-926229

Reference yield: 40.0%

trans-4-methoxy-3-buten-2-one (51731-17-0) + 2-(pivaloylamino)pyridine (86847-59-8) → 4-methyl[1,8]-naphthyridine (1569-17-1)

Guidance literature:

2-(pivaloylamino)pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 3h;

trans-4-methoxy-3-buten-2-one; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h;

With hydrogenchloride; Heating;

DOI:10.1055/s-2006-926229

upstream raw materials:

2,7-dichloro-5-methyl-1,8-naphtyridine

(E)-4-(dimethylamino)but-3-en-2-one

2-(pivaloylamino)pyridine

(E)-3-(dimethylamino)acrolein

Downstream raw materials:

1,8-naphthyridine-4-carboxaldehyde

1a,1b,2,7b-tetrahydro-7-methyl-1,2-bis(phenylsulfonyl)-1H-azirino<1.2-a>cyclopropa<1.8>naphthyridine

Refernces

• 1、 Magee, Thomas V.,Ripp, Sharon L.,Li, Bryan,Buzon, Richard A.,Chupak, Lou,Dougherty, Thomas J.,Finegan, Steven M.,Girard, Dennis,Hagen, Anne E.,Falcone, Michael J.,Farley, Kathleen A.,Granskog, Karl,Hardink, Joel R.,Huband, Michael D.,Kamicker, Barbara J.,Kaneko, Takushi,Knickerbocker, Michael J.,Liras, Jennifer L.,Marra, Andrea,Medina, Ivy,Nguyen, Thuy-Trinh,Noe, Mark C.,Obach, R. Scott,O'Donnell, John P.,Penzien, Joseph B.,Reilly, Usa Datta,Schafer, John R.,Shen, Yue,Stone, Gregory G.,Strelevitz, Timothy J.,Sun, Jianmin,Tait-Kamradt, Amelia,Vaz, Alfin D. N.,Whipple, David A.,Widlicka, Daniel W.,Wishka, Donn G.,Wolkowski, Joanna P.,Flanagan, Mark E.. "Discovery of azetidinyl ketolides for the treatment of susceptible and multidrug resistant community-acquired respiratory tract infections". experimental part. p. 7446 - 7457. Retrieved 2010/06/13.