120427-94-3

Usage

Uses

Used in Organic Synthesis:
2-(2-BROMOETHYL)-BETA-NITROSTYRENE is used as a key intermediate in the synthesis of complex organic molecules for various applications, including the development of new pharmaceuticals and organic compounds. Its unique chemical properties facilitate various chemical reactions and transformations in the laboratory, contributing to the advancement of organic chemistry.
Used in Drug Development:
In the pharmaceutical industry, 2-(2-BROMOETHYL)-BETA-NITROSTYRENE is utilized as a building block in the creation of novel drug candidates. Its potential applications in the preparation of various pharmaceuticals highlight its importance in drug discovery and development processes, where it can be employed to design and synthesize new therapeutic agents with improved efficacy and selectivity.
Used in Chemical Research:
2-(2-BROMOETHYL)-BETA-NITROSTYRENE serves as a valuable research tool in chemical research, where it can be used to study the reactivity and properties of β-nitrostyrene derivatives. Its unique chemical characteristics make it an interesting subject for exploring new reaction pathways and mechanisms, ultimately contributing to the broader understanding of organic chemistry and its applications.

Upstream product

• 75-52-5 nitromethane 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 50683-32-4 1-Bromoisochromane 
• 493-05-0 isochromane 

Downstream Products

• 120427-93-2 4-ethylenyl-1,3-dihydro-2H-indol-2-one 
• 120427-95-4 4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one 
• 120427-96-5 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one 
• 91374-20-8 ropinirole hydrochloride 

Relevant academic research and scientific papers

Preparation method of 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone

The invention provides a preparation method of 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone, and the preparation method of the 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone is characterized in that the 4-(2-bromoethyl)-1, 3-dihydro-2H-indole-2-ketone is prepared by taking o-bromoethyl benzaldehyde as an initial raw material and carrying out a series of reactions. The raw materials are cheap and easy to obtain, the product yield and purity are high, and the method has excellent economic and environment-friendly benefits.

PROCESS FOR PURIFICATION OF ROPINIROLE

The invention discloses an improved process for the purification of ropinirole hydrochloride by dissolving or suspending crude ropinirole base or its pharmaceutically acceptable salt in a suitable solvent, reacting with a nitrogenous base to form an imine derivative, optionally treating the reaction mixture with a base to adjust the pH, and isolating purified ropinirole hydrochloride. The invention also provides for a pharmaceutical composition comprising pure ropinirole hydrochloride as active ingredient.

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.