N~2~,N~6~-Bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide

Base Information

• Chemical Name: N~2~,N~6~-Bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide
• CAS No.: 96308-77-9
• Molecular Formula: C19H15N3O4
• Molecular Weight: 349.346
• DSSTox Substance ID: DTXSID90557457
• Nikkaji Number: J1.244.154A
• Wikidata: Q82439371
• Mol file: 96308-77-9.mol

Synonyms:96308-77-9;SCHEMBL1086005;DTXSID90557457;N~2~,N~6~-Bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide;n,n'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide

Chemical Property of N~2~,N~6~-Bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide

Chemical Property:

• PSA: 115.04000
• LogP: 3.45440
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 349.10625597
• Heavy Atom Count: 26
• Complexity: 459

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)NC(=O)C2=NC(=CC=C2)C(=O)NC3=CC=CC=C3O)O

Technology Process of N~2~,N~6~-Bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide

There total 2 articles about N~2~,N~6~-Bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamide 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: 95.0%

2,6-Pyridinedicarbonyl dichloride (3739-94-4) + 2-amino-phenol (95-55-6) → N,N'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide (96308-77-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1139/V08-153

Reference yield:

Pyridine-2,6-dicarboxylic acid (499-83-2) → N,N'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide (96308-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methyl-2-pyrrolidone, thionyl chloride

2: Heating

With 1-methyl-pyrrolidin-2-one; thionyl chloride;

DOI:10.1002/hlca.19800630212

Reference yield: 72.0%

nickel(II) chloride hexahydrate + N,N'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide (96308-77-9) + potassium hydroxide → K[Ni(N,N'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide(-3H))] (1269514-23-9)

Guidance literature:

In acetonitrile; KOH added to stirred soln. of ligand in MeCN at 70°C; stirred for15 min; soln. of NiCl2*6H2O in hot MeCN added; heated under reflux for 3 h; cooled to 25°C; filtered; recrystd. from hot MeOH; elem. anal.;

DOI:10.1016/j.poly.2010.10.012

upstream raw materials:

2,6-Pyridinedicarbonyl dichloride

2-amino-phenol

Pyridine-2,6-dicarboxylic acid

Downstream raw materials:

2,6-bis(benzoxazol-2-yl)pyridine

K[Ni(N,N'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide(-3H))]

[triethylammonium][Ni(N,N'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide(-3H))]

[triethylammonium][PdCl(N,N'-bis(2-hydroxyphenyl)-pyridine-2,6-dicarboxamide(-2H))]

Refernces

• 1、 Khalifeh, Reza,Sharghi, Hashem,Rashidi, Zahra. "Synthesis of [Zn(II)BHPPDAH] as new heterogeneous catalyst without being immobilized on any support and applied for mannich reaction". . p. 372 - 383. Retrieved 2013/09/23.
• 2、 Sharghi, Hashem,Hosseini-Sarvari, Mona,Moeini, Fatemeh. "Copper-catalyzed one-pot synthesis of benzimidazole derivatives". experimental part. p. 1044 - 1051. Retrieved 2009/02/08.