32372-82-0

Usage

Uses

Isoindoline hydrochloride is used as pharmaceutical intermediate.

InChI:InChI=1/C8H9N.ClH/c1-2-4-8-6-9-5-7(8)3-1;/h1-4,9H,5-6H2;1H

Upstream product

• 91-13-4 α,α'-dibromo-o-xylene 
• 6921-28-4 dipropargylamine 
• 74-86-2 acetylene 
• 38379-25-8 o-chloromethylbenzylamine 
• 136918-14-4 phthalimide 
• 4152-92-5 2-(hydroxymethyl)benzylamine 
• 91-15-6 phthalonitrile 

Downstream Products

• 685565-70-2 N-[4-(3-piperidin-1-ylpropoxy)benzoyl]isoindoline 
• 914296-91-6 (5-bromo-2-hydroxyphenyl)(isoindolin-2-yl)methanone 
• 32372-83-1 2(toluene-p-sulphonyl)isoindoline 
• 1470-99-1 cis-hexahydroisoindoline 
• 855630-88-5 isoindoline-2-carbothioamide 

Relevant academic research and scientific papers

Stereoelectronic Suppresion and a Remarkably Low Effective Concentration for a Cyclization to a Benzo-fused Five-membered Ring

The cyclization of o-chloromethylbenzylamine to dihydroisoindole has an effective concentration of 8.3 M (in CD3OD at 21 deg C); this very low value for a cyclization to a benzo-fused five-membered ring is ascribed to lessend conjugation in the transition state as compared to that of the model reaction, and is relevant to both the synthesis of rings and the application of effective concentrations in obtaining evidence of mechanism.

Solid-supported [2+2+2] cyclotrimerizations

The transition-metal-catalyzed [2+2+2] cyclotrimerization of a diyne and an alkyne provides a convergent route to highly-substituted aromatic rings. This reaction possesses distinct drawbacks, especially low chemo-and regioselectivities, which hamper its

Selenoxide elimination triggers enamine hydrolysis to primary and secondary amines: A combined experimental and theoretical investigation

We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density functional theory (DFT).

Method for preparing amine compound by reducing amide compound

The invention relates to a method for preparing an amine compound by reducing an amide compound, which comprises the following steps: in a protective atmosphere, mixing the amide compound or cyclic amide, a zirconium metal catalyst and pinacol borane, carrying out amide reduction reaction at room temperature, and carrying out aftertreatment by using an ether solution of hydrogen chloride after 12-48 hours to obtain an amine hydrochloride compound. The method is simple to operate, low in cost, good in functional group tolerance and wide in substrate range.

Straightforward access to cyclic amines by dinitriles reduction

1,1,3,3-Tetramethyldisiloxane (TMDS) and polymethylhydrosiloxane (PMHS), when associated with titanium(IV) isopropoxide, provide two convenient systems for the reduction of nitriles into the corresponding primary amines. Kinetics of the two systems have been studied by 1H NMR and demonstrated that reduction with PMHS occurs faster than with TMDS. These two titanium-based systems reduce both aromatic and aliphatic nitriles in the presence of Br, CC, NO2, OH, and cyclopropyl-ring. In the case of cyclopropyl-nitriles, the formation of secondary amines, which come from an intermolecular reductive alkylation reaction was observed. This result was exploited for the reduction of dinitriles, which led, in one-step, to azepane, piperidine, pyrrolidine, and azetidine derivatives through an intramolecular reductive alkylation reaction.

New process for the preparation of isoindoline

Process for the industrial synthesis of isoindoline by catalytic hydrogenation of phthalonitrile. Application in the synthesis of 2-(S)-benzyl-4-oxo-4-(cis-perhydroisoindol-2-yl)-butyric acid, its pharmaceutically acceptable salts and its hydrates.