54520-83-1

Basic information

• Product Name: 2-Pyrrolidinone, 1-methyl-5-phenyl-
• Synonyms: 1-methyl-5-phenyl-2-pyrrolidinone;1-methyl-5-phenyl-pyrrolidin-2-one;N-methyl-5-phenyl-2-pyrrolidone;2-Pyrrolidinone,1-methyl-5-phenyl;1-Methyl-5-phenyl-pyrrolidon-(2);1-Methyl-5-phenyl-pyrrolidin-2-on;N-Methyl-4-phenylpyrrolidin-2-on
• CAS NO: 54520-83-1
• Molecular Formula: C11H13NO
• Molecular Weight: 175.23
• Mol File: 54520-83-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinone, 1-methyl-5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinone, 1-methyl-5-phenyl-(54520-83-1)
• EPA Substance Registry System: 2-Pyrrolidinone, 1-methyl-5-phenyl-(54520-83-1)

Safety Data

• Hazardous Substances Data: 54520-83-1(Hazardous Substances Data)

Upstream product

• 23132-30-1 5-Hydroxy-1-methyl-5-phenylpyrrolidin-2-one 
• 2051-95-8 succinylbenzene 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 6907-71-7 N-(1-phenylethylidene)methanamine 
• 938-36-3 1-methyl-2-phenylpyrrolidine 
• 99-61-6 3-nitro-benzaldehyde 
• 446-52-6 2-Fluorobenzaldehyde 
• 1955-39-1 5-phenyl-3H-furan-2-one 
• 142609-28-7 2,2-dichloro-N-methyl-N-(1-phenylvinyl)acetamide 
• 142609-27-6 2-chloro-N-methyl-N-(1-phenylvinyl)acetamide 
• 41194-00-7 5-Hydroxy-N-methyl-2-pyrrolidone 
• 71-43-2 benzene 
• 72442-37-6 1-methyl-5-oxopyrrolidine-2-carboxylic acid 

Downstream Products

• 22050-10-8 (+/-)-5-phenyl-2-pyrrolidinone 
• 23132-29-8 4-oxo-4-phenylbutanamide 
• 103859-83-2 N-methyl-4-oxo-4-phenylbutanamide 
• 61021-23-6 3-[2-(1-Methyl-5-phenyl-2-pyrrolidinylideneamino)ethylthio]indole cyclohexanesulfamate 

Relevant articles and documents

Superacid promoted reactions of N-acyliminium salts and evidence for the involvement of superelectrophiles

Experimental and theoretical studies suggest the involvement of dicationic, superelectrophilic N-acyliminium ions in conversions catalyzed by superacids. The Royal Society of Chemistry.

Enamine trapping with the oxidation of nicotine and analogues

Various N-tertiary pyrrolidine derivatives 1 and 6-9 bearing voluminous substituents in 2-position react with Hg(II)-EDTA under double dehydrogenation and an atypical direction to the secondary C-5 with formation of the corresponding lactams 2 and 12-15. The primary products of a two electron withdrawal cannot be isolated. By addition of substituted benzaldehydes b-d as trapping reagents to the Hg(II)-EDTA solution additionally are received condensation products of the type of benzylidene lactams 1b-d, 6b,c and 7b-9b. Here the total yield of isolated products increases, while simultaneously the yield of unsubstituted lactams of the type 2 and 12-15 decreases. Therefore the atypical direction of dehydrogenation with the trapping aldehydes is the same as with the lactam forming pyrrolidines. Additionally the detection of the enamine species in the first stage of dehydrogenation with following reaction to the condensation product is secured. The (E)-configuration of 1b is confirmed by the chemical shift of the proton a-H and the 19F/13C-coupling constant of C-4 by direct comparison with its (Z)-isomer 27. The similar signal dates of the enone protons in the other prepared benzylidene lactams 1c,d, as well as 6b,c and 7b-9b verify also the (E)-configuration.

Synthesis of pyrrolidin-2-ones by 5-endo-trigonal radical cyclisation of N-vinyl-2,2-bis(phenylsulfanyl)acetamides

A series of N-methyl-N-(1-substituted or 1,2-disubstituted vinyl)-2,2-bis(phenylsulfanyl)acetamides, upon treatment with tributyltin hydride in the presence of a catalytic amount of AIBN in boiling toluene, underwent smooth cyclisation in a 5-endo-trig ma