295357-72-1

Basic information

• Product Name: 2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid
• Synonyms: 2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid
• CAS NO: 295357-72-1
• Molecular Weight: 308.247
• Mol File: 295357-72-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid(295357-72-1)
• EPA Substance Registry System: 2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid(295357-72-1)

Safety Data

• Hazardous Substances Data: 295357-72-1(Hazardous Substances Data)

Usage

Description

2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid is a chemical compound that is an impurity of Lenalidomide (L328000), an immunomodulatory drug, and an analog of Thalidomide.

Uses

Used in Pharmaceutical Industry:
2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid is used as an impurity in the production of Lenalidomide, an immunomodulatory drug. It is important to monitor and control the levels of this impurity to ensure the safety and efficacy of Lenalidomide as a medication.

Upstream product

• 827026-43-7 2-(4-nitro-1-oxo-1,3-dihydroisoindol-2-yl)glutaric acid dimethyl ester 
• 59382-59-1 2-methyl-3-nitro-benzoic acid methyl ester 
• 98475-07-1 2-bromomethyl-3-nitro-benzoic acid methyl ester 
• 617-65-2 Glutamic acid 
• 366452-97-3 4-nitroisoindolin-1-one 

Downstream Products

• 295357-66-3 2-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)glutaric acid 
• 879126-98-4 Lenalidomide 

Relevant articles and documents

Preparation method of lenalidomide

A preparation method of lenalidomide comprises the following steps: 1, reacting a raw material methyl 2-methyl-3-nitro-benzoate with a halogenating reagent to obtain methyl 2-halomethyl-3-nitro-benzoate represented by formula (I); 2, reacting the methyl 2-halomethyl-3-nitro-benzoate with dimethyl D,L-glutamate hydrochloride in the presence of an alkaline compound to obtain dimethyl 3-(7-nitro-1-oxo-1,3-dihydroisoindole-2-yl)glutarate represented by formula (II); 3, hydrolyzing the above compound of formula (II) to obtain 3-(7-nitro-1-oxo-1,3-dihydroisoindole-2-yl)glutaric acid represented by formula (III); 4, reducing the above compound of formula (III) to obtain 3-(7-amino-1-oxo-1,3-dihydroisoindole-2-yl)glutaric acid represented by formula (IV); and 5, carrying out ring closure on the above compound of formula (IV) to obtain lenalidomide represented by formula (V). The method has the advantages of simple process, high safety, cheap and easily available raw materials, good quality of the above product, and suitableness for industrial production.

Substituted 1-oxo- and 1,3-dioxoisoindoline and method of reducing inflammatory cytokine levels

1-Oxo- and 1,3-dioxoisoindolines substituted in the 4- or 5-position of the indoline ring reduce the levels of inflammatory cytokines such as TNFα in a mammal. A typical embodiment is 4-(4-amino-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid.