353497-35-5

Upstream product

• 3335-98-6 1-phenyl-1,3-dihydro-indol-2-one 
• 79-22-1 methyl chloroformate 
• 616-38-6 carbonic acid dimethyl ester 
• 805236-74-2 [2-(methoxycarbonyl-phenyl-amino)-phenyl]-acetic acid methyl ester 

Downstream Products

• 353497-31-1 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester 
• 731851-81-3 {2-[Phenyl-(2,2,2-trifluoro-acetyl)-amino]-phenyl}-acetic acid 
• 731851-78-8 [2-(benzyl-phenyl-amino)-phenyl]-acetic acid 
• 731851-92-6 (2-phenylamino-phenyl)-acetic acid benzyl ester 
• 731851-88-0 [2-(acetyl-phenyl-amino)-phenyl]-acetic acid 
• 39507-06-7 (2-phenylamino-phenyl)-acetic acid methyl ester 
• 70172-33-7 2-[2-(phenylamino)phenyl]acetic acid 
• 28721-09-7 10-methoxy-5H-dibenz[b,f]azepine-5-carboxamide 
• 4698-11-7 10-methoxy-5H-dibenzo[b,f]azepine 
• 21737-58-6 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one 
• 28721-07-5 oxcarbazepine 
• 3335-98-6 1-phenyl-1,3-dihydro-indol-2-one 

Relevant academic research and scientific papers

A new industrial process for oxcarbazepine

A novel industrial process for the antiepileptic drug oxcarbazepine 1 has been developed. Unlike the old process, the new process is free from halogenated solvents and can be performed in standard production equipment. It starts from commercially available 1,3-dihydro-1-phenyl-2H-indol-2-one 10. In the key step, an electrophilic ring closure reaction of 2-[(methoxycarbonyl)phenylamino] benzeneacetic acid 5 to 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester 6 in poly phosphoric acid was applied. For the manufacture of 5, a highly efficient process using a dianion strategy was developed.

A new synthesis of oxcarbazepine using a Friedel-Crafts cyclization strategy

A novel, simple, and straightforward process for the large-scale synthesis of oxcarbazepine, the active ingredient of Trileptal, a medicine for the treatment of epilepsy, has been developed. Starting from readily available 1,3-dihydro-1-phenyl-2H-indol-2-one, a Friedel-Crafts cyclization strategy provides a direct route to the tricyclic framework of the target molecule. Crucial to the success of the strategy was the choice of the proper nitrogen-protecting group.

Dibenzo(b,f)azepine derivatives and their preparation

The invention relates to new processes for the preparation of the pharmaceutical oxcarbazepine, as well as novel intermediates prepared by or used for said processes, and the preparation of said intermediates.