108444-19-5

Basic information

• Product Name: 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one
• Synonyms: 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one
• CAS NO: 108444-19-5
• Molecular Weight: 255.273
• Mol File: 108444-19-5.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one(108444-19-5)
• EPA Substance Registry System: 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-isoindol-1-one(108444-19-5)

Safety Data

• Hazardous Substances Data: 108444-19-5(Hazardous Substances Data)

Upstream product

• 2142-04-3 2-(4-methoxyphenyl)isoindoline-1,3-dione 
• 104-94-9 4-methoxy-aniline 
• 7554-80-5 N-(4'-methoxyphenyl)phthalamic acid 
• 85-44-9 phthalic anhydride 
• 7472-54-0 N-(p-methoxyphenyl)benzamide 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 108444-16-2 ethyl 2-(2-(4-methoxyphenyl)-3-oxoisoindolin-1-yl)acetate 
• 88460-55-3 2,3-Dihydro-3-oxo-2-(p-methoxyphenyl)-1H-isoindole-1-acetic Acid 
• 132868-77-0 2,3-Dihydro-3-oxo-2-phenyl-1H-isoindole-1-acetyl Chloride 
• 2142-04-3 2-(4-methoxyphenyl)isoindoline-1,3-dione 
• 59099-81-9 methyl 2,3-diphenyl-1H-indene-1-carboxylate 

Relevant articles and documents

Stereoselective cycloaddition of N-acyliminium ions with α,β-unsaturated ketones and esters

The [4+2] reactions of N-acyliminium ions, produced from 2-aryl-3-hydroxy-2,3-dihydroisoindol-1-onesor5-hydroxy-1-phenyl-2,5-dihydro/2,3,4,5-tetrahydropyrrol-2-ones in the presence of BF3OEt2, with α,β-unsaturated ketones or esters w

The behavior of 2-substituted-3-hydroxyisoindolinones in the reaction with sec-butyllithium

This paper presents a dualistic behavior of 2-substituted-3- hydroxyisoindolones in reactions with sec-butyllithium (sec-BuLi). 2-tert-Butyl-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (1a) treated with sec-BuLi undergoes metalation at position 7. On the other hand, the reaction between 3-hydroxy-2-phenyl-2,3-dihydroxyisoindol-1-one (1j) and sec-BuLi results in 3-sec-butyl-2-phenyl-2,3-dihydroisiondol-1-one (3j).

An Oxidation Study of Phthalimide-Derived Hydroxylactams

A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.

Aza-DielsAlder reaction between N-aryl-1-oxo-1H-isoindolium ions and tert-enamides: Steric effects on reaction outcome

The synthesis of 5-substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)- ones via [4 + 2] imino-DielsAlder cyclization from N-aryl-3- hydroxyisoindolinones and N-vinyl lactams under Lewis acid-catalysed anhydrous conditions is reported. Reactions of N-(2-substituted-aryl)-3- hydroxyisoindolinones with N-vinylpyrrolidone under identical conditions resulted in the formation of 2-(2-substitued-aryl)-3-(2-(2-oxopyrrolidin-1-yl) vinyl)isoindolin-1-one analogues indicating steric hinderance as the cause of deviation. The probable mechanism of the reaction based on the results from X-ray crystallography and molecular modelling is discussed.