120427-93-2

Usage

Uses

Used in Pharmaceutical Industry:
4-Ethenyl-1,3-dihydro-2H-indol-2-one is used as a decomposition product for Ropinirole N-oxide, which is significant in the pharmaceutical industry. Its role as a decomposition product indicates its potential involvement in the synthesis or modification of other pharmaceutical compounds, contributing to the development of new drugs or the improvement of existing ones.
As a decomposition product, 4-Ethenyl-1,3-dihydro-2H-indol-2-one may also be utilized in research and development for understanding the chemical transformations and reactions that occur during the synthesis or degradation of Ropinirole N-oxide and related compounds. This knowledge can be applied to optimize pharmaceutical processes and enhance the efficacy and safety of medications.

InChI:InChI=1/C10H9NO/c1-2-7-4-3-5-9-8(7)6-10(12)11-9/h2-5H,1,6H2,(H,11,12)

Upstream product

• 139122-16-0 benzoic acid (2-(2-nitroethenyl))phenethyl ester 
• 139122-15-9 benzoic acid (2-formyl)phenethyl ester 
• 107-10-8 propylamine 
• 120427-96-5 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one 
• 1426679-27-7 2-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]acetic acid 
• 1441070-77-4 ethyl 3-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]-2-oxopropanoate 
• 1426679-26-6 1-[(2-methyl-3-nitrophenethyloxy)methyl]benzene 
• 855382-76-2 2-(2-methyl-3-nitrophenyl)ethyl alcohol 
• 168476-58-2 2-[2-(chloromethyl)phenyl]ethylbenzoate 
• 23876-15-5 2-(3-nitro-2-methylphenyl)acetic acid 
• 493-05-0 isochromane 
• 139122-19-3 4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one 
• 139122-18-2 4-(2-benzoyloxyethyl)-1,3-dihydro-2H-indolin-2-one 
• 139122-17-1 4-[2-(benzoyloxy)ethyl]-3-chloro-1,3-dihydro-2H-indolin-2-one 

Relevant academic research and scientific papers

A convenient synthesis of 4-(2-hydroxyethyl)indolin-2-one, a useful intermediate for the preparation of both dopamine receptor agonists and protein kinase inhibitors

This paper describes a practical approach to the preparation of 4-(2-hydroxyethyl)indolin-2-one, a key intermediate in the synthesis of dopaminergic agonists such as ropinirole - a drug used in the treatment of Parkinson's disease and restless legs syndrome - and of two sets of protein kinase inhibitors. The sequence starts from commercially available 2-(2-methyl-3-nitrophenyl)acetic acid, which is converted in five steps into the desired target compound. This procedure offers a convenient alternative route to existing methodologies, given its milder reaction conditions, ease of implementation, and its overall yield (59 %).

Development of large-scale syntheses of ropinirole in the pursuit of a manufacturing process

Two plant syntheses of ropinirole {4-[2-(di-n-propyIamino)-ethyl]-1,3-dihydro-2H-indolin-2-one hydrochloride, SK&F-101468-A} using the ferric chloride mediated cyclisation of β-nitrostyrenes to form 3-chlorooxindoles as the key step are described. The first synthesis suffered the severe limitation of the final-step chemistry being nonselective in the reaction between di-n-propylamine and the bromide precursor to ropinirole as both substitution and elimination pathways were promoted and by-product formation at a level of 40% resulted. This problem was rectified in the latter synthesis by the more selective reaction between di-n-propylamine and the sulfonate ester precursor promoting ropinirole formation to a level of 88%. This second synthesis is now used as the commercial route, and problems (and their solutions) identified during the development of this route are now described. The identification of novel by-products which enabled the Sommelet oxidation step to be optimised is also reported. A unimolecular decomposition mechanism during hydrolysis of the hexaminium salt to form the key benzaldehyde intermediate is proposed and substantiated with experimental data.

Some synthetic approaches to ropinirole (SK and F 101468-A): A potent dopamine receptor agonist

Three new routes to ropinirole (SK and F 101468-A, 1) are described each involving the preparation of 3-chlorooxindole intermediates of type 3 from β-nitrostyrenes as the pivotal step. The superiority of sulphonate esters 17a-c as direct precursors to 1 over the bromide 11 is also described.