92264-37-4

Basic information

• Product Name: 2-(benzoylamino)indole
• Synonyms: 2-(benzoylamino)indole
• CAS NO: 92264-37-4
• Molecular Weight: 236.273
• Mol File: 92264-37-4.mol

Chemical Properties

• CAS DataBase Reference: 2-(benzoylamino)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(benzoylamino)indole(92264-37-4)
• EPA Substance Registry System: 2-(benzoylamino)indole(92264-37-4)

Safety Data

• Hazardous Substances Data: 92264-37-4(Hazardous Substances Data)

Upstream product

• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 1616115-84-4 N-methoxy-1H-indole-1-carboxamide 
• 154224-25-6 C₁₅H₁₃N₃O₄ 
• 154224-26-7 3-(2-nitrobenzyl)-5-phenyl-1,2,4-oxadiazole 
• 154224-24-5 2-(2-nitrophenyl)acetamide oxime 
• 610-66-2 2-nitro-benzeneacetonitrile 
• 154224-12-1 Benzyl-[2-(5-phenyl-[1,2,4]oxadiazol-3-ylmethyl)-phenyl]-amine 
• 154224-28-9 3-(2-aminobenzyl)-5-phenyl-1,2,4-oxadiazole 

Downstream Products

• 59-48-3 2-oxoindole 
• 55-21-0 benzamide 
• 154224-29-0 6-phenyl-8H-pyrimido<1,6-a:4,5-b'>diindole 

Relevant articles and documents

Chameleon-like Behavior of the Directing Group in the Rh(III)-Catalyzed Regioselective C-H Amidation of Indole: An Experimental and Computational Study

The Rh(III)-catalyzed regioselective C-H amidation of N-methoxy-1H-indole-1-carboxamides by 1,4,2-dioxazol-5-ones was studied. N-Methoxy amide, the directing group (DG) of interest, undergoes four different transformations through DG-retained, -coupled, -eliminated, or -migrated processes under moderately varied reaction conditions. Solvents, additives, and temperature play important roles in these selective transformations; a trace addition of water favors the functional group (FG)-assisted DG elimination; extra addition of KHSO4 greatly enhances the formation of the DG-coupled product; high-temperature and proper FG together can shift the position of DG through intermolecular Friedel-Crafts-like acylation. The catalytic mechanisms underlying these reactions were further investigated through density functional theory calculations and experimental studies including the characterization of amido-inserted rhodacycle. An overall catalytic pathway was proposed to illustrate the reactions involved in the regioselective amidation of N-methoxy-1H-indole-1-carboxamide.

Reductive Formation of 2-(Benzoylamino)indole from 3-(2-Aminobenzyl)-5-phenyl-1,2,4-oxadiazole and Its Transfomation to 6-Phenyl-8H-pyrimido-diindole, a New Heterocyclic Ring System

Catalytic hydrogenation of 5-substituted 3-(2-aminobenzyl)-1,2,4-oxadiazoles 7 give 2-(acylamino)indoles 10.Treatment of 2-(benzoylamino)indoles 10a-c with acid leads to the novel 6-phenyl-8H-pyrimidodiindoles 19a-c.A route for the new ring formation is proposed.Catalytic hydrogenation of 19a (Raney nickel, 70 deg C, atmospheric pressure) saturates the 6-phenyl ring but leaves the pentacyclic ring system intact.The structure of 19a is confirmed by an X-ray crystallographic analysis. - Key Words: 1,2,4-Oxadiazoles, 5-substituted, 3-(2-aminobenzyl)- / Indoles, 2-(acylamino)- / 8H-Pyrimidodiindoles, 6-aryl