120427-95-4

Usage

Chemical Properties

Light brown or off -white power

InChI:InChI=1/C10H9BrClNO/c11-5-4-6-2-1-3-7-8(6)9(12)10(14)13-7/h1-3,9H,4-5H2,(H,13,14)

Upstream product

• 120427-94-3 2-(2-bromoethyl)-β-nitrostyrene 
• 120427-94-3 2-(2-bromoethyl)-β-nitrostyrene 
• 75-36-5 acetyl chloride 
• 50683-32-4 1-Bromoisochromane 
• 493-05-0 isochromane 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 

Downstream Products

• 120427-96-5 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one 
• 91374-20-8 ropinirole hydrochloride 
• 120427-93-2 4-ethylenyl-1,3-dihydro-2H-indol-2-one 
• 139122-20-6 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl-4-methylbenzene-1-sulfonate 
• 139122-22-8 2-(2'-oxo-2,3-dihydro-4-indolyl)ethyl benzenesulphonate 
• 139122-19-3 4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one 
• 91374-21-9 Ropinirole 

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.

Process for preparing substituted isoindolinone derivatives

This invention relates to an improved process for the preparation of substituted indolinone derivatives using reductive cyclization conditions.