1H-Pyrrole-2-carboxylicacid,5-cyano-,methylester(9CI)

Base Information

• Chemical Name: 1H-Pyrrole-2-carboxylicacid,5-cyano-,methylester(9CI)
• CAS No.: 937-19-9
• Molecular Formula: C7H6 N2 O2
• Molecular Weight: 150.13
• Hs Code.: 2933990090
• Mol file: 937-19-9.mol

Synonyms:Pyrrole-2-carboxylicacid, 5-cyano-, methyl ester (7CI,8CI); 5-Cyano-1H-pyrrole-2-carboxylic acidmethyl ester; Methyl 5-cyanopyrrole-2-carboxylate

Chemical Property of 1H-Pyrrole-2-carboxylicacid,5-cyano-,methylester(9CI)

Chemical Property:

• PSA: 65.88000
• LogP: 0.67298
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

methyl5-cyano-1H-pyrrole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrole-2-carboxylicacid,5-cyano-,methylester(9CI)

There total 10 articles about 1H-Pyrrole-2-carboxylicacid,5-cyano-,methylester(9CI) 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: 71.0%

methyl 5-formyl-1H-pyrrole-2-carboxylate (1197-13-3) → 5-cyano-1H-pyrrole-2-carboxylic acid methyl ester (937-19-9)

Guidance literature:

methyl 5-formyl-1H-pyrrole-2-carboxylate; With AMINOHIPPURATE SODIUM; hydroxylamine hydrochloride; In methanol; for 1h; Reflux;

With trichlorophosphate; In N,N-dimethyl-formamide; at -20 - 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2015.03.012

Reference yield: 24.0%

methyl Pyrrole-2-carboxylate (1193-62-0) + isocyanate de chlorosulfonyle (1189-71-5) → 5-cyano-1H-pyrrole-2-carboxylic acid methyl ester (937-19-9)

Guidance literature:

In N,N-dimethyl-formamide; acetonitrile; at -40 - 20 ℃; for 24h;

DOI:10.1021/jo400372c

Reference yield:

methyl Pyrrole-2-carboxylate (1193-62-0) + isocyanate de chlorosulfonyle (1189-71-5) → methyl 4-cyanopyrrole-2-carboxylate (937-18-8) + 5-cyano-1H-pyrrole-2-carboxylic acid methyl ester (937-19-9)

Guidance literature:

With N,N-dimethyl-formamide; Yield given. Multistep reaction; 1.) acetonitrile, ice bath, 5 min, room temp., overnight; 2.) ice bath then 50 deg C, 15 min;

upstream raw materials:

methyl Pyrrole-2-carboxylate

isocyanate de chlorosulfonyle

methyl 5-cyano-1-hydroxy-1H-pyrrole-2-carboxylate

ethyl 1H-pyrrole-2-carboxylate

Downstream raw materials:

C₁₃H₁₂N₆O

5-carboxy-1H-pyrrole-2-carbonitrile

Refernces

• 1、 Chen, Jianyang,Peng, Haixia,He, Jinxue,Huan, Xiajuan,Miao, Zehong,Yang, Chunhao. "Synthesis of isoquinolinone-based tricycles as novel poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors". . p. 2669 - 2673. Retrieved 2014/06/09.
• 2、 Loader, Charles E.,Anderson, Hugh J.. "Pyrrole chemistry. XXIII. The cyanation of substituted pyrroles with chlorosulfonyl isocyanate (CSI). New syntheses of pyrrole-3-carbonitriles". . p. 2673 - 2676. Retrieved 2007/10/02.