1H-Pyrrole-2-carboxylic acid, 1-(4-methylphenyl)-, methyl ester

Base Information

• Chemical Name: 1H-Pyrrole-2-carboxylic acid, 1-(4-methylphenyl)-, methyl ester
• CAS No.: 144062-62-4
• Molecular Formula: C13H13NO2
• Molecular Weight: 215.252
• DSSTox Substance ID: DTXSID80434900
• Wikidata: Q82249487
• Mol file: 144062-62-4.mol

Synonyms:1H-Pyrrole-2-carboxylic acid, 1-(4-methylphenyl)-, methyl ester;SCHEMBL16204335;DTXSID80434900

Chemical Property of 1H-Pyrrole-2-carboxylic acid, 1-(4-methylphenyl)-, methyl ester

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 215.094628657
• Heavy Atom Count: 16
• Complexity: 246

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)N2C=CC=C2C(=O)OC

Technology Process of 1H-Pyrrole-2-carboxylic acid, 1-(4-methylphenyl)-, methyl ester

There total 8 articles about 1H-Pyrrole-2-carboxylic acid, 1-(4-methylphenyl)-, methyl 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: 80.0%

N-propargyl-4-methylaniline (22774-64-7) + methyl 2-methoxy-2-(piperidin-1-yl)acetate (13887-54-2) → 1-(4-methylphenyl)-1H-pyrrole-2-carboxylic acid methyl ester (144062-62-4)

Guidance literature:

With copper dichloride; In toluene; at 100 ℃; for 2h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1002/ejoc.201500098

Reference yield:

1-(4-methylphenyl)-1H-pyrrole-2-carboxylic acid (35524-50-6) → 1-(4-methylphenyl)-1H-pyrrole-2-carboxylic acid methyl ester (144062-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 4 h / 25 °C

2: 16 h / 25 °C

With thionyl chloride;

DOI:10.1021/jm00053a013

Reference yield:

1-(4-methylphenyl)-1H-pyrrole (827-60-1) → 1-(4-methylphenyl)-1H-pyrrole-2-carboxylic acid methyl ester (144062-62-4)

Guidance literature:

Multi-step reaction with 5 steps

1: POCl₃ / 3 h / 110 - 120 °C

2: 1.) H₂NOH*HCl/Na₂CO₃, 2.) Ac₂O / 1.) MeOH, H₂O, reflux, 3 h, 2.) reflux, 3 h

3: KOH / ethane-1,2-diol / 4 h / 167 °C

4: SOCl₂ / 4 h / 25 °C

5: 16 h / 25 °C

With potassium hydroxide; thionyl chloride; hydroxylamine hydrochloride; acetic anhydride; sodium carbonate; trichlorophosphate; In ethylene glycol;

DOI:10.1021/jm00053a013

upstream raw materials:

1-(4-methylphenyl)-1H-pyrrole

1-(4-methylphenyl)-2-formyl-1H-pyrrole

1-(4-methylphenyl)pyrrole-2-carbonitrile

1-(4-methylphenyl)-1H-pyrrole-2-carboxylic acid

Downstream raw materials:

methyl 1-<4-(bromomethyl)phenyl>-1H-pyrrole-2-carboxylate