40707-01-5

Basic information

• Product Name: 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE
• Synonyms: 2H-3,1-Benzoxazine-2,4(1H)-dione, 5-chloro-1-Methyl-;5-chloro-1-Methyl-2H-benzo[d][1,3]oxazine-2,4(1H)-dione;5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;5-chloro-1-methyl-3,1-benzoxazine-2,4-dione
• CAS NO: 40707-01-5
• Molecular Formula: C₉H₆ClNO₃
• Molecular Weight: 211.60184
• Mol File: 40707-01-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 344.8 °C at 760 mmHg
• Flash Point: 162.3 °C
• Appearance: /
• Density: 1.476 g/cm³
• Vapor Pressure: 6.42E-05mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.48±0.20(Predicted)
• CAS DataBase Reference: 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE(40707-01-5)
• EPA Substance Registry System: 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE(40707-01-5)

Safety Data

• Hazardous Substances Data: 40707-01-5(Hazardous Substances Data)

Usage

General Description

5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE is a chemical compound that belongs to the class of benzo[d][1,3]oxazine-2,4-diones. It is a chlorinated derivative of the parent compound, with a chloro group and a methyl group attached to the benzo[d][1,3]oxazine ring. 5-CHLORO-1-METHYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE is a heterocyclic organic compound and can be used in various chemical and pharmaceutical applications. Its chemical structure and properties make it useful for research and development in the fields of medicine, materials science, and chemical synthesis. Due to its potential applications, it is important to handle and use this compound with care, following proper safety protocols and guidelines.

InChI:InChI=1/C9H6ClNO3/c1-11-6-4-2-3-5(10)7(6)8(12)14-9(11)13/h2-4H,1H3

Upstream product

• 20829-96-3 5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione 
• 616-38-6 carbonic acid dimethyl ester 
• 2148-56-3 2-chloro-6-aminobenzoic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 

Downstream Products

• 248281-84-7 laquinimod 
• 1383427-58-4 ingenol-5,20-acetonide-3-(2-chloro-6-methylamino-benzoate) 
• 637027-41-9 1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxo-quinoline-3-carboxylic acid methyl ester 
• 248282-10-2 5-chloro-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester 

Relevant articles and documents

An Efficient Method for the Synthesis of Laquinimod

Laquinimod, 5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N- phenyl-3-quinoline carboxamide, is an oral drug in clinical trials for the treatment of multiple sclerosis. An efficient synthetic method for laquinimod from 2-amino-6-chlorobenzoic acid via four steps was established. The overall yield of laquinimod is up to 82% as compared with 70% reported in literature. It has also been demonstrated that green reagent dimethyl carbonate is not suitable for the N-methylation of 5-chloroisatoic anhydride owing to the ring-cleavage reaction induced by the generated methanol. The ring-cleavage by-products were isolated and characterized by 1H-NMR and 13C-NMR. In addition, in the study of laquinimod derivatives, we found that 5-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinoline carboxamide (laquinimod) was obtained in much higher yield than 7-chloro-1,2-dihydro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinoline carboxamide under the same reaction conditions, and it is possibly attributed to a neighboring group effect.

Heterocyclic GSK-3 Allosteric Modulators

The present invention relates to heterocyclic substituted quinoline derivatives as allosteric inhibitors of the glycogen synthase kinase-3 (GSK-3) enzyme. Therefore, these compounds are useful for the manufacturing of a medicament designed for the treatme

HIGHLY PURE LAQUINIMOD OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Provided herein is an impurity of laquinimod, N-ethyl-N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide (deschloro laquinimod impurity), and process for preparation and isolation thereof. Provided further herein is a highly pure laquinimod or a pharmaceutically acceptable salt thereof substantially free of deschloro laquinimod impurity, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure laquinimod or a pharmaceutically acceptable salt thereof substantially free of deschloro laquinimod impurity.