3-Hydroxy-2-naphthalenecarboxylic acid 2-[(2-hydroxy-3-methoxyphenyl)methylene]hydrazide

Base Information

• Chemical Name: 3-Hydroxy-2-naphthalenecarboxylic acid 2-[(2-hydroxy-3-methoxyphenyl)methylene]hydrazide
• CAS No.: 80648-85-7
• Molecular Formula: C₁₉H₁₆N₂O₄
• Molecular Weight: 336.347
• DSSTox Substance ID: DTXSID301123632
• Mol file: 80648-85-7.mol

Synonyms:DTXSID301123632;3-Hydroxy-2-naphthalenecarboxylic acid 2-[(2-hydroxy-3-methoxyphenyl)methylene]hydrazide;80648-85-7

Chemical Property of 3-Hydroxy-2-naphthalenecarboxylic acid 2-[(2-hydroxy-3-methoxyphenyl)methylene]hydrazide

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 336.11100700
• Heavy Atom Count: 25
• Complexity: 484

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=CC(=C1O)C=NNC(=O)C2=CC3=CC=CC=C3C=C2O

Technology Process of 3-Hydroxy-2-naphthalenecarboxylic acid 2-[(2-hydroxy-3-methoxyphenyl)methylene]hydrazide

There total 4 articles about 3-Hydroxy-2-naphthalenecarboxylic acid 2-[(2-hydroxy-3-methoxyphenyl)methylene]hydrazide 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: 98.0%

3-hydroxy-2-naphthohydrazide (5341-58-2) + 3-methoxy-2-hydroxybenzaldehyde (148-53-8) → (E)-3-hydroxy-N′-(2-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide (80648-85-7)

Guidance literature:

In methanol; for 3h; Reflux;

DOI:10.1016/j.ica.2010.04.046

Reference yield:

3-Hydroxy-2-naphthoic acid (92-70-6) → (E)-3-hydroxy-N′-(2-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide (80648-85-7)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / water / 90 °C

2: hydrazine hydrate / ethanol / 0.25 h / 120 °C

3: ethanol / 6 h / 120 °C

With hydrogenchloride; hydrazine hydrate; In ethanol; water;

DOI:10.1021/ci400189m

Reference yield:

3-hydroxy-2-naphthoic acid methyl ester (883-99-8) → (E)-3-hydroxy-N′-(2-hydroxy-3-methoxybenzylidene)-2-naphthohydrazide (80648-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrazine hydrate / ethanol / 0.25 h / 120 °C

2: ethanol / 6 h / 120 °C

With hydrazine hydrate; In ethanol;

DOI:10.1021/ci400189m

upstream raw materials:

3-hydroxy-2-naphthohydrazide

3-methoxy-2-hydroxybenzaldehyde

3-hydroxy-2-naphthoic acid methyl ester

3-Hydroxy-2-naphthoic acid

Refernces

• 1、 Caboni, Laura,Egan, Billy,Kelly, Brendan,Blanco, Fernando,Fayne, Darren,Meegan, Mary J.,Lloyd, David G.. "Structure-activity relationships in non-ligand binding pocket (Non-LBP) diarylhydrazide antiandrogens". . p. 2116 - 2130. Retrieved 2013/09/23.
• 2、 Osman, M. M.,Ali, G. Y.. "COMPLEXES OF Co(II), Ni(II) AND Zn(II) WITH 3-HYDROXY-2-NAPHTHOYL HYDRAZONES OF SOME AROMATIC ALDEHYDES". . p. 13 - 24. Retrieved 2007/10/02.