51786-47-1

Basic information

• Product Name: N-phenyl-2,5-dimethylacetanilide
• CAS NO: 51786-47-1
• Molecular Weight: 239.317
• Mol File: 51786-47-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-phenyl-2,5-dimethylacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: N-phenyl-2,5-dimethylacetanilide(51786-47-1)
• EPA Substance Registry System: N-phenyl-2,5-dimethylacetanilide(51786-47-1)

Safety Data

• Hazardous Substances Data: 51786-47-1(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 2050-44-4 N-(2,5-dimethylphenyl)acetamide 
• 553-94-6 4-bromo-m-xylene 
• 103-84-4 Acetanilid 

Downstream Products

• 32446-14-3 2,5-dimethylphenyl(phenyl)amine 

Relevant articles and documents

A GENERAL SYNTHESIS OF 6-H-PYRIDOCARBAZOLE ALKALOIDS

A general and versatile synthesis of the 6-H-pyridocarbazole alkaloid ellipticine is described; the approach employs the coupling of an acetanilide with a bromoisoquinoline followed by heterocyclic ring formation to give ellipticine.

Exploratory Routes to Carbazole Derivatives Prelusive to 6H-Pyridocarbazole synthesis.

Synthetic approaches to 3-acyl substituted carbazoles are explored.Diels-Alder additions of 2-methyl-3-trimethylsilyloxybuta-1,3-diene (7) with crotononitrile or methyl vinyl ketone gave stereoisomeric 5-cyano (or acetyl) 1-methyl-2-trimethylsilyloxy-cyclohex-1-enes.The former were readily hydrolysed to the corresponding cyclohexanones which failed to undergo Borsche cyclisation under the conditions used.The latter were reduced and then hydrolysed to a stereoisomeric mixture of 4-(1-hydroxyethyl)-2-methyl- cyclohexanones (14).The Borsche cyclisation of (14) with phenylhydrazine was attempted under a wide variety of conditions followed by attempted dehydrogenation of the intermediate tetrahydrocarbazoles with chloranil, but loss of the hydroxyethyl side chain took place giving 1-methylcarbazole as the sole isolable carbazole.In the second approach a number of N-acyl substituted diphenylamines are synthesised by the Goldberg reaction.Those lacking a 4-substituent undergo a photo-anilide rearrangement which is accompanied by carbazole formation.Diphenylamides with a 4- substituent, after hydrolysis to the diphenylamines, undergo photochemical cyclisation to 3- carbazoles but in low yield.The Goldberg synthesis of 4-formyldiphenylamides affords substantial amounts of the 4-formyldiphenylamines after work-up.These, on reaction with palladium(II) acetate in acetic acid give a mixture of products including the required 3-formyl (or carboxyl) carbazoles.