157846-99-6

Basic information

• Product Name: Methanone, (1-methyl-1H-pyrrol-2-yl)(4-nitrophenyl)-
• CAS NO: 157846-99-6
• Molecular Formula: C12H10N2O3
• Molecular Weight: 230.223
• Mol File: 157846-99-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Methanone, (1-methyl-1H-pyrrol-2-yl)(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (1-methyl-1H-pyrrol-2-yl)(4-nitrophenyl)-(157846-99-6)
• EPA Substance Registry System: Methanone, (1-methyl-1H-pyrrol-2-yl)(4-nitrophenyl)-(157846-99-6)

Safety Data

• Hazardous Substances Data: 157846-99-6(Hazardous Substances Data)

Upstream product

• 96-54-8 N-Methylpyrrole 
• 4231-71-4 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone 
• 7506-46-9 N-cyclohexyl-4-nitrobenzamide 
• 619-72-7 4-nitrobenzonitrile 
• 62-23-7 4-nitro-benzoic acid 
• 28122-84-1 4-nitrothiobenzoic acid S-p-tolyl ester 
• 118486-97-8 1-methyl-2-(tributyltin)pyrrole 
• 122-04-3 4-nitro-benzoyl chloride 
• 60-29-7 diethyl ether 
• 52728-54-8 1,1-dimethyl-2-n-propylhydrazine 

Downstream Products

• 157847-10-4 2-Chloro-1-[5-(4-nitrobenzoyl)-1-methyl-1H-pyrrol-3-yl]-ethanone 
• 1338919-43-9 (2R)-2-{1-methyl-5-[(4-nitrophenyl)carbonyl]-1H-pyrrol-3-yl}-2-hydroxyacetic acid n-butyl ester 

Relevant articles and documents

Metal-Free Intermolecular Coupling of Arenes with Secondary Amides: Chemoselective Synthesis of Aromatic Ketimines and Ketones, and N-Deacylation of Secondary Amides

The direct transformation of common secondary amides into aromatic ketimines and aromatic ketones with C-C bond formation is described. The reaction can also be used for N-deacylation of secondary amides to release amines. This method consists of in situ amide activation with triflic anhydride and intermolecular capture of the resulting highly electrophilic nitrilium intermediate with an arene. The reaction is applicable to various kinds of secondary amides (electrophiles), but only electron-rich and moderately electron-rich arenes can be used as nucleophiles. Thanks to the use of bench stable arenes instead of reactive and basic organometallics as nucleophiles, the reaction proceeded with high chemoselectivity at the secondary amido group in the presence of a series of sensitive functional groups such as aldehyde, ketone, ester, cyano, nitro, and tertiary amido groups. The reaction can be viewed as a Friedel-Crafts-type reaction using secondary amides as acylating agents or as an intermolecular version of the Bischler-Napieralski reaction.

Friedel - Crafts acylation of pyrroles and indoles using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) as a nucleophilic catalyst

1,5-Diazabicyclo[4.3.0]non-5-ene (DBN) has been shown to be an effective catalyst for the regioselective Friedel - Crafts C-acylation of pyrroles and indoles in high yields. A detailed mechanistic study implies that DBN is acting as a nucleophilic organocatalyst, with the X-ray crystal structure of a key N-acyl-amidine intermediate having been determined for the first time.

Regiospecific C-acylation of pyrroles and indoles using N-acylbenzotriazoles

Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a - g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2