182572-80-1

Basic information

• Product Name: N-(4-hydroxy-2-methylphenyl)-3,3-diphenylpropanamide
• Synonyms: N-(4-hydroxy-2-methylphenyl)-3,3-diphenylpropanamide
• CAS NO: 182572-80-1
• Molecular Formula: C22H21NO2
• Molecular Weight: 331.40764
• Mol File: 182572-80-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-hydroxy-2-methylphenyl)-3,3-diphenylpropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-hydroxy-2-methylphenyl)-3,3-diphenylpropanamide(182572-80-1)
• EPA Substance Registry System: N-(4-hydroxy-2-methylphenyl)-3,3-diphenylpropanamide(182572-80-1)

Safety Data

• Hazardous Substances Data: 182572-80-1(Hazardous Substances Data)

Upstream product

• 102-50-1 2-methyl-4-methoxyaniline 
• 102-92-1 Cinnamoyl chloride 
• 143268-85-3 4-methoxy-2-methylcinnamanilide 
• 71-43-2 benzene 

Relevant articles and documents

Lewis acid catalyzed reaction of cinnamanilides: Competition of intramolecular and intermolecular Friedel-Crafts reaction

The first intermolecular Friedel-Crafts reaction of benzene leading to the formation of 3,3-diphenylpropionanilide 7 is described. 4-Methoxyaniline was reacted with cinnamoyl chloride to give 4-methoxycinnamanilide (5a), the treatment of which with aluminum (III) chloride in chlorobenzene at 120 °C or in benzene at 80 °C afforded exclusively 6-hydroxyquinolin-2(1H)-one (3a) or 4'-hydroxy-3,3-diphenylpropionanilide (7a), respectively. The formation of 7a rather than 3a in benzene indicated that an intermolecular Friedel-Crafts reaction occurred prior to the relatively more facile intramolecular ring cyclization. This intermolecular Friedel-Crafts reaction was observed during the attempted ring cyclization of cinnamanilide and its methoxy derivatives in aluminum (III) chloride/benzene. Preparation of 3a can also be achieved in 17% overall yield via the N-oxidation of 6-hydroxyquinoline followed by acetylation and hydrolysis.