N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide

Base Information

• Chemical Name: N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide
• CAS No.: 55654-71-2
• Molecular Formula: C17H14 N2 O2
• Molecular Weight: 278.31
• DSSTox Substance ID: DTXSID80971007
• Nikkaji Number: J630.996H
• Wikidata: Q82954423
• ChEMBL ID: CHEMBL75289
• Mol file: 55654-71-2.mol

Synonyms:BnIn-3-GA;N-(indol-3-ylglyoxylyl)benzylamine;N-benzylindole-3-glyoxylamide

Chemical Property of N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide

Chemical Property:

• Vapor Pressure: 3.98E-11mmHg at 25°C
• Boiling Point: 525.3°C at 760 mmHg
• Flash Point: 271.5°C
• PSA: 61.96000
• Density: 1.24g/cm³
• LogP: 3.05790
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 278.105527694
• Heavy Atom Count: 21
• Complexity: 390

Purity/Quality:

99% ，98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(=O)C(=O)C2=CNC3=CC=CC=C32

Technology Process of N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide

There total 6 articles about N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide 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: 75.0%

indolyl-3-glyoxylyl chloride (22980-09-2) + benzylamine (100-46-9) → N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide (55654-71-2)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2007.04.035

Reference yield: 65.0%

3-(1H-indol-3-yl)-3-oxo-propionitrile (20356-45-0) + benzylamine (100-46-9) → N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide (55654-71-2)

Guidance literature:

With sodium percarbonate; potassium carbonate; In 1,4-dioxane; at 80 ℃; for 6h; Green chemistry;

DOI:10.1002/ejoc.201900900

Reference yield:

indole (120-72-9) → N-benzyl-2-(1H-indol-3-yl)-2-oxoacetamide (55654-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether

2: diethyl ether

With diethyl ether;

upstream raw materials:

indolyl-3-glyoxylyl chloride

benzylamine

indole

Indole-3-carboxaldehyde

Downstream raw materials:

C₃₇H₃₂N₄O₄

C₄₂H₃₄N₄O₄

2-benzylamino-1-(1-methyl-indol-3-yl)-ethanol

N-benzyl-2-hydroxy-2-(1H-indol-3-yl)acetamide

Refernces

• 1、 Barresi, Elisabetta,Giacomelli, Chiara,Marchetti, Laura,Baglini, Emma,Salerno, Silvia,Greco, Giovanni,Da Settimo, Federico,Martini, Claudia,Trincavelli, Maria Letizia,Taliani, Sabrina. "Novel positive allosteric modulators of A2B adenosine receptor acting as bone mineralisation promoters". . p. 286 - 294. Retrieved 2020/12/22.
• 2、 Ghoshal, Anirban,Ambule, Mayur D.,Sravanthi, Revoju,Taneja, Mohit,Srivastava, Ajay Kumar. "Copper-catalyzed oxidative cleavage of Passerini and Ugi adducts in basic medium yielding α-ketoamides". . p. 14459 - 14474. Retrieved 2019/10/01.