4-Hydroxy-1-(4-methylphenyl)-3-pyrazolecarboxylic acid ethyl ester

Base Information

• Chemical Name: 4-Hydroxy-1-(4-methylphenyl)-3-pyrazolecarboxylic acid ethyl ester
• CAS No.: 26502-59-0
• Molecular Formula: C₁₃H₁₄N₂O₃
• Molecular Weight: 246.266
• DSSTox Substance ID: DTXSID101185983
• Wikidata: Q27183021
• ChEMBL ID: CHEMBL1363746
• Mol file: 26502-59-0.mol

Synonyms:ethyl 4-hydroxy-1-(4-methylphenyl)pyrazole-3-carboxylate;26502-59-0;4-hydroxy-1-(4-methylphenyl)-3-pyrazolecarboxylic acid ethyl ester;ethyl 4-hydroxy-1-(4-methylphenyl)-1H-pyrazole-3-carboxylate;1H-Pyrazole-3-carboxylic acid, 4-hydroxy-1-(4-methylphenyl)-, ethyl ester;MLS000067724;Oprea1_065462;Oprea1_521323;CHEMBL1363746;CHEBI:105303;DTXSID101185983;HMS2170D13;HMS3315D09;4-Hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester;STL306254;AKOS000540132;SMR000125067;CS-0299017;AF-399/15394013;SR-01000370641;SR-01000370641-1;Q27183021;Z56884639;Ethyl 4-hydroxy-1-(p-tolyl)-1h-pyrazole-3-carboxylate

Chemical Property of 4-Hydroxy-1-(4-methylphenyl)-3-pyrazolecarboxylic acid ethyl ester

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 246.10044231
• Heavy Atom Count: 18
• Complexity: 290

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=NN(C=C1O)C2=CC=C(C=C2)C

Technology Process of 4-Hydroxy-1-(4-methylphenyl)-3-pyrazolecarboxylic acid ethyl ester

There total 2 articles about 4-Hydroxy-1-(4-methylphenyl)-3-pyrazolecarboxylic acid ethyl ester 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: 3.0%

ethyl 4-chloroacetoacetate + p-methylbenzenediazonium chloride (2028-84-4) → 4-hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester (26502-59-0) + C14H15ClN2O5 + C14H15ClN2O5

Guidance literature:

With sodium acetate; In water; acetone; for 2h; Cooling with ice;

DOI:10.1002/jhet.1787

Reference yield:

4-bromo-3-oxo-2-p-tolylhydrazono-butyric acid ethyl ester (24123-53-3) → 4-hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester (26502-59-0)

Guidance literature:

With sodium acetate; In ethanol; for 3h; Heating;

Reference yield: 66.0%

4-hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester (26502-59-0) + 5-Amino-3-methyl-4-phenylpyrazole diazonium chloride → ethyl 1-(p-tolyl)-5-[(3-methyl-4-phenyl-1H-pyrazol-5-yl)hydrazono]-4-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate

Guidance literature:

With sodium acetate; acetic acid; In water; at 20 ℃;

DOI:10.1002/jhet.1533

upstream raw materials:

4-bromo-3-oxo-2-p-tolylhydrazono-butyric acid ethyl ester

p-methylbenzenediazonium chloride

Downstream raw materials:

4-hydroxy-1-(4-methylphenyl)-1H-pyrazole-3-carboxylic acid hydrazide

Refernces

Synthesis of new azocompounds and fused pyrazolo[5,1-c][1,2,4]triazines using heterocyclic components

10.1002/jhet.1533

The study, titled "Synthesis of New Azocompounds and Fused Pyrazolo[5,1-c][1,2,4]triazines Using Heterocyclic Components," investigates the synthesis of new azocompounds and tricyclic pyrazolo[5,1-c][1,2,4]triazines using various heterocyclic components. The key chemical involved is 3-methyl-4-phenyl-1H-pyrazol-5-amine, which is diazotized to form pyrazole-3(5)-diazonium chloride. This diazonium salt undergoes azocoupling reactions with a variety of heterocyclic compounds, including barbituric acid, thiobarbituric acid, 2-hetarylpyrimidine-4,6-diones, 4-hydroxy-6-methylpyridin-2(1H)-one, 4-hydroxy-6-methyl-2H-pyran-2-one, 4-hydroxy-1-p-tolyl-1H-pyrazole-3-carboxylic acid ethyl ester, 1,3-thiazolidine-2,4-dione, and 2-thioxo-1,3-thiazolidin-4-one. These reactions yield new pyrazolylazo derivatives and fused pyrazolo[5,1-c][1,2,4]triazines through subsequent heterocyclization processes. The study explores the synthetic potential of these heterocyclic components in azocoupling reactions, highlighting their potential applications in industrial azo dyes, analytical indicators, and bioactive compounds related to purines.