91374-21-9

Basic information

• Product Name: Ropinirole
• Synonyms: ROPINIROLE;4-(2-dipropylaminoethyl)-1,3-dihydroindol-2-one;ROPINIROLE 99%;ROPINIROLE: ROPINIROLE HYDROCHLORIDE;ROPINIROLE INTERMEIDATES:;4-[2-(Dipropylamino)ethyl]-1，3-dihydrcr2H-indol-2-one;SKF-101468;SKF-101468A：ReQuip
• CAS NO: 91374-21-9
• Molecular Formula: C₁₆H₂₄N₂O
• Molecular Weight: 260.37
• Product Categories: Pharmaceutical material and intermeidates;Antiparkinsonian;ACTIVE PHARMACEUTICAL INGREDIENTS;API
• Mol File: 91374-21-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 243-250°C
• Boiling Point: 410.5 °C at 760 mmHg
• Flash Point: 202 °C
• Appearance: White or yellowish crystalline powder
• Density: 1.04 g/cm³
• Vapor Pressure: 6.01E-07mmHg at 25°C
• Refractive Index: 1.538
• PKA: 14.17±0.20(Predicted)
• CAS DataBase Reference: Ropinirole(CAS DataBase Reference)
• NIST Chemistry Reference: Ropinirole(91374-21-9)
• EPA Substance Registry System: Ropinirole(91374-21-9)

Safety Data

• Hazardous Substances Data: 91374-21-9(Hazardous Substances Data)

Usage

Uses

Antiparkinsonian (D2receptor agonist).

Clinical Use

Anti-Parkinson agent Restless legs syndrome (RLS)

Drug interactions

Potentially hazardous interactions with other drugs Antipsychotics: antagonism of anti-Parkinsonian effect - avoid. Metoclopramide: antagonism of anti-Parkinsonian effect - avoid. Oestrogens: concentration increased.

Metabolism

Ropinirole is hepatically metabolised by the cytochrome P450 enzyme, CYP1A2, and excreted in the urine as inactive metabolites.

InChI:InChI=1/C16H24N2O/c1-3-9-18(10-4-2)11-8-13-6-5-7-15-14(13)12-16(19)17-15/h5-7H,3-4,8-12H2,1-2H3,(H,17,19)

Upstream product

• 91374-25-3 <2-nitro-6-<2-(N,N-di-n-propylamino)ethyl>phenyl>acetic acid hydrochloride 
• 142-84-7 di-n-propylamine 
• 120427-96-5 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one 
• 139122-21-7 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl methanesulfonate 
• 139122-22-8 2-(2'-oxo-2,3-dihydro-4-indolyl)ethyl benzenesulphonate 
• 139122-20-6 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl-4-methylbenzene-1-sulfonate 
• 106-94-5 propyl bromide 
• 173990-76-6 4-<2-(N-propylamino)ethyl>-2-indolone hydrochloride 
• 720656-64-4 2-nitro-6-<2-(di-n-propylamino)ethyl>phenylacetic acid 
• 493-05-0 isochromane 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 95033-78-6 1-hydroxyisochroman 
• 139122-19-3 4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one 
• 120427-94-3 2-(2-bromoethyl)-β-nitrostyrene 

Downstream Products

• 91374-20-8 ropinirole hydrochloride 

Relevant articles and documents

Synthesis of 2-Oxindoles from Substituted Indoles by Hypervalent-Iodine Oxidation

A practical conversion of indoles into the corresponding 2-oxindoles is achieved efficiently using a hypervalent iodine reagent. This oxidation is amenable to different substituted indoles, and allows the synthesis of a wide range of synthetically valuable substituted 2-oxindoles in up to 90 % yield. Furthermore, Ropinirole, a drug used to alleviate the symptoms of Parkinson's disease, was synthesized in three steps in an overall yield of 44 % using this method.

The development of a short route to the API ropinirole hydrochloride

A four-step, three-stage synthesis of the API ropinirole hydrochloride has been developed from a commercially available naphthalene derivative. The new route has half the step-count and twice the overall yield of the current manufacturing process. Key features of the synthesis are a regioselective Birch reduction and an ozonolysis with concomitant ring closure to induce the required ring contraction.

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 %).