Methyl 6-amino-4-indolecarboxylate

Base Information

• Chemical Name: Methyl 6-amino-4-indolecarboxylate
• CAS No.: 103956-00-9
• Molecular Formula: C10H10N2O2
• Molecular Weight: 190.202
• Hs Code.: 2933990090
• Mol file: 103956-00-9.mol

Synonyms:Methyl 6-amino-1H-indole-4-carboxylate;

Chemical Property of Methyl 6-amino-4-indolecarboxylate

Chemical Property:

• Vapor Pressure: 1.36E-07mmHg at 25°C
• Refractive Index: 1.694
• Boiling Point: 429.8 °C at 760 mmHg
• PKA: 17.03±0.30(Predicted)
• Flash Point: 213.7 °C
• PSA: 68.11000
• Density: 1.339 g/cm³
• LogP: 2.11790
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature

Purity/Quality:

98%min ^*data from raw suppliers

Methyl6-amino-4-indolecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 6-amino-4-indolecarboxylate

There total 5 articles about Methyl 6-amino-4-indolecarboxylate 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: 21.0%

methyl 2-methyl-3,5-dinitrobenzoate (52090-24-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → methyl 6-amino-1H-indole-4-carboxylate (103956-00-9)

Guidance literature:

methyl 2-methyl-3,5-dinitrobenzoate; N,N-dimethyl-formamide dimethyl acetal; In DMF (N,N-dimethyl-formamide); at 120 ℃;

With hydrogen; palladium 10% on activated carbon; In DMF (N,N-dimethyl-formamide); for 5h; under 2844.39 Torr;

Reference yield:

(E)-methyl 2-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate → methyl 6-amino-1H-indole-4-carboxylate (103956-00-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 48h;

Reference yield:

methyl 2-methyl-3,5-dinitrobenzoate (52090-24-1) → methyl 6-amino-1H-indole-4-carboxylate (103956-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.25 h / 60 °C / microwave irradiation

2: H₂ / Pd/C / methanol

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/j.bmcl.2006.11.059

upstream raw materials:

methyl 2-methyl-3,5-dinitrobenzoate

N,N-dimethyl-formamide dimethyl acetal

3,5-dinitro-o-toluic acid

Downstream raw materials:

6-{2-[5-chloro-2-(benzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-1H-indole-4-carboxylic acid methyl ester

6-((tert-butoxycarbonyl)amino)-1H-indole-4-carboxylic acid

methyl 6-((tert-butoxycarbonyl)amino)-1H-indole-4-carboxylate

C₁₇H₁₆N₂O₄S

Refernces

• 1、 Hall, Adrian,Brown, Susan H.,Chessell, Iain P.,Chowdhury, Anita,Clayton, Nicholas M.,Coleman, Tanya,Giblin, Gerard M.P.,Hammond, Beverley,Healy, Mark P.,Johnson, Matthew R.,Metcalf, Ann,Michel, Anton D.,Naylor, Alan,Novelli, Riccardo,Spalding, David J.,Sweeting, Jennifer,Winyard, Lisa. "1,5-Biaryl pyrrole derivatives as EP1 receptor antagonists. Structure-activity relationships of 6-substituted and 5,6-disubstituted benzoic acid derivatives". . p. 916 - 920. Retrieved 2007/10/03.
• 2、 -. "PYRROLE COMPOUNDS FOR THE TREATMENT OF PROSTAGLANDIN MEDIATED DISEASES". Page 245-246. . Retrieved 2010/02/05.