1134192-59-8

Basic information

• Product Name: 3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one
• Synonyms: 3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one
• CAS NO: 1134192-59-8
• Molecular Weight: 357.409
• Mol File: 1134192-59-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one(1134192-59-8)
• EPA Substance Registry System: 3-hydroxy-1-(4-methoxybenzyl)-4-phenylquinolin-2(1H)-one(1134192-59-8)

Safety Data

• Hazardous Substances Data: 1134192-59-8(Hazardous Substances Data)

Upstream product

• 3526-43-0 N-(4-methoxybenzyl)aniline 
• 100-52-7 benzaldehyde 

Downstream Products

• 129-24-8 4-phenyl-3-hydroxyquinolin-2(1H)-one 

Relevant articles and documents

Synthesis and Mechanistic Insights of the Formation of 3-Hydroxyquinolin-2-ones including Viridicatin from 2-Chloro- N,3-diaryloxirane-2-carboxamides under Acid-Catalyzed Rearrangements

N-Benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, easily obtained from aromatic aldehydes and anilides of dichloroacetic acid under Darzens condensation conditions, proved to be excellent starting compounds for the synthesis of 3-hydroxyindolin-2-ones, cyclohepto[b]pyrrole-2,3-diones, and 1-azaspiro[4.5]deca-3,6,9-triene-2-ones via the C(sp2)-C(sp2) bond formation in the first case and C(sp2)-C(sp3) bond formation in the second and third cases. Under optimized reaction conditions, 3-hydroxyindolin-2-ones are obtained in a one-pot process, which involves the treatment of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides with CF3CO2H or AcOH/H2SO4. In the case of intramolecular cyclization, the detailed reaction channels depend strongly on the substituents present in the anilide component and in the aromatic ring of the aldehyde component of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, as well as the temperature and duration of the reaction. A combined experimental and DFT mechanistic study of the formation of 1-benzyl-3-hydroxy-4-arylquinolin-2(1H)-ones showed that there are three competing reaction channels: (a) ring-closure via the ipso site, (b) ring-closure via the 1,2-Cl shift, and (c) ring-closure via the ortho site. Such mechanistic insights enabled an effective one-pot gram-scale synthesis of viridicatin from benzaldehyde and 2,2-dichloro-N-(4-methoxybenzyl)-N-phenylacetamide.