17372-63-3

Basic information

• Product Name: 1H-Isoindol-1-one, 2,3-dihydro-2-(2-methylphenyl)-
• CAS NO: 17372-63-3
• Molecular Formula: C15H13NO
• Molecular Weight: 223.274
• Mol File: 17372-63-3.mol

Chemical Properties

• CAS DataBase Reference: 1H-Isoindol-1-one, 2,3-dihydro-2-(2-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindol-1-one, 2,3-dihydro-2-(2-methylphenyl)-(17372-63-3)
• EPA Substance Registry System: 1H-Isoindol-1-one, 2,3-dihydro-2-(2-methylphenyl)-(17372-63-3)

Safety Data

• Hazardous Substances Data: 17372-63-3(Hazardous Substances Data)

Usage

General Description

The chemical 1H-Isoindol-1-one, 2,3-dihydro-2-(2-methylphenyl)- is a heterocyclic organic compound with the molecular formula C15H13NO. It is also known by the name "2,3-dihydro-2-(2-tolyl)-1H-isoindol-1-one" and is a derivative of isoindoline. 1H-Isoindol-1-one, 2,3-dihydro-2-(2-methylphenyl)- is commonly used as a building block in the synthesis of pharmaceuticals and other organic compounds. It has also been found to have potential biological activities, including anti-cancer and anti-inflammatory properties. The presence of the methylphenyl group on the 2-position of the isoindolone ring contributes to its unique chemical and biological properties, making it an important compound in the field of medicinal chemistry and drug discovery.

Upstream product

• 95-53-4 o-toluidine 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 201230-82-2 carbon monoxide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 119-67-5 o-carboxybenzaldehyde 
• 933-88-0 ortho-toluoyl chloride 
• 22978-49-0 2-methyl-N-(2-methylphenyl)benzamide 
• 73357-43-4 2-(2-methylphenyl)-2,3-dihydro-1H-isoindole 
• 91-13-4 α,α'-dibromo-o-xylene 

Relevant articles and documents

Twisted intramolecular charge-transfer fluorescence of aromatic amides: Conformation of the amide bonds in the excited states

The mechanism of the dual fluorescences of benzanilide (1) and N-methylbenzanilide (2) in methylcyclohexane was investigated. The emission at longer wavelength is composed of one component for 1 (λmax 477 nm) and of one major component (96%, λ

Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines

N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones.

Ruthenium(ii)-catalysed selective C(sp2)-H bond benzoxylation of biologically appealing: N -arylisoindolinones

Site- and regio-selective aromatic C-H bond benzoxylations were found to take place using biologically appealing N-arylisoindolinones under ruthenium(ii) catalysis in the presence of (hetero)aromatic carboxylic acid derivatives as coupling partners. Besides the presence of two potential C(sp2)-H sites available for functionalization in the substrates, exclusive ortho selectivity was achieved in the phenyl ring attached to the nitrogen atom. Notably, the reactions occurred in a selective manner as only mono-functionalized products were formed and they tolerated a large number of functional chemical groups. The ability of the cyclic tertiary amide within the isoindolinone skeleton to act as a weak directing group in order to accommodate six-membered ring ruthenacycle intermediates appears to be the key to reach such high levels of selectivity. In contrast, the more sterically demanding cyclic imides were unreactive under identical reaction conditions.

Site-Selective Ruthenium-Catalyzed C-H Bond Arylations with Boronic Acids: Exploiting Isoindolinones as a Weak Directing Group

Biologically relevant N-arylisoindolinones efficiently underwent arylation reactions under ruthenium catalysis via C-H bond functionalization. The reactions exclusively led to monoarylated products, and only ortho selectivity was observed in the aromatic ring connected to the nitrogen atom. Interestingly, no C-H bond functionalization was observed in the other benzene ring in the ortho position with respect to the carbonyl group. This ruthenium-catalyzed reaction displayed a high functional group tolerance, and it employed readily available and benchmark stable boronic acid and potassium aryltrifluoroborate derivatives as coupling partners. An appealing late-stage functionalization of indoprofen applying this methodology is showcased.

Selective and Efficient Iridium Catalyst for the Reductive Amination of Levulinic Acid into Pyrrolidones

The catalytic reductive amination of levulinic acid (LA) into pyrrolidones with an iridium catalyst using H2 as hydrogen source is reported. The chemoselective iridium catalyst displayed high efficiency for the synthesis of a variety of N-substituted 5-methyl-2-pyrrolidones and N-arylisoindolinones. N-Substituted 5-methyl-2-pyrrolidone was also evaluated as a biosourced substitute solvent to NMP (N-methylpyrrolidone) in the catalytic arylation of 2-phenylpyridine.

A facile and efficient method for the synthesis of N-substituted isoindolin-1-one derivatives under Pd(OAc)2/HCOOH system

A facile and efficient method for the synthesis of N-substituted isoindolin-1-one derivatives from 2-formylbenzoic acid and amine under Pd(OAc)2/HCOOH system has been described. The whole process is carried out in ligand-free conditions and furnished the desired products by reductive intramolecular cyclization. Furthermore, this procedure is applied successfully for the modification of natural products, such as vindoline and estrone.

Application of the mild-condition phthalimidine synthesis with use of 1,2,3-1h-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries. Effective synthesis of phthalimidines possessing a variety of substituents at 2-position

The mild-condition phthalimidine synthesis based on Mannich type 1:1 condensation reaction between o-phthalaldehyde with a variety of primary amines in the presence of excess 2-mercaptoethanol and 1,2,3-1H-benzotriazole as "dual synthetic auxiliaries" in MeCN for 13 h at room temperature afford 2-substituted phthalimidines (2,3-dihydroisoindol-1-one) in fair to good isolated yields.

Transition metal free intramolecular selective oxidative C(sp3)-N coupling: Synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp3)-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 °C.

Synthesis of substituted amines and isoindolinones: Catalytic reductive amination using abundantly available AlCl3/PMHS

AlCl3 has been employed for highly chemoselective reductive amination of carbonyl compounds in ethanol using polymethylhydrosiloxane as an inexpensive, stable and safe reducing agent without an inert atmosphere. A large range of functional groups such as nitro, carboxylic acid, acetyl, nitrile, halogen, methoxy, alkene and heterocycles were well tolerated. AlCl3 also catalyzed tandem amination-amidation of 2-carboxybenzaldehyde with different amines to afford N-substituted isoindolinones. The catalyst can be recycled at least three times without any significant effect on activity and selectivity.

Highly efficient synthesis of N-substituted isoindolinones and phthalazinones using Pt nanowires as catalysts

A series of N-substituted isoindolinones have been successfully synthesized through the reductive C-N coupling and intramolecular amidation of 2-carboxybenzaldehyde and amines. This one-pot synthesis gives excellent yields using ultrathin Pt nanowires as catalysts under 1 bar of hydrogen. These unsupported catalysts can also be used for the synthesis of phthalazinones in high yield when hydrazine or phenyl hydrazine is used instead of amines.