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

Method for preparing ropinirole hydrochloride

The invention belongs to the technical field of medicinal chemistry and organic chemistry, and particularly relates to a method for preparing ropinirole hydrochloride. A novel compound 4 is synthesized by the aid of the method and is used as a raw material for preparing the ropinirole hydrochloride. The particular method includes dissolving the compound 4 in one or a plurality of types of ethyl alcohol/methanol/ethyl acetate to obtain liquid, adding Pd/C into the ethyl alcohol/methanol/ethyl acetate, and carrying out reaction to obtain compounds 5; dissolving the compounds 5, p-toluenesulfonylchloride and pyridine in one or a plurality of types of dichloromethane/trichloromethane/1, 2-dichloroethane/pyridine, and carrying out reaction to obtain compounds 6; dissolving the compounds 6, NaIand dipropyl amine in one or a plurality of types of DMF (dimethyl formamide)/DMSO (dimethylsulfoxide)/Toluene, and carrying out reaction to obtain ropinirole; dissolving the ropinirole in 1, 4 dioxane with hydrochloric acid, and carrying out reduced-pressure compression to obtain the ropinirole hydrochloride. A proportion of the compounds 5 to the p-toluenesulfonyl chloride to the pyridine is equal to 1:1.2:1.2. A proportion of the compounds 6 to the NaI to the dipropyl amine is equal to 1:1:1.2. The novel method for preparing the ropinirole hydrochloride has the advantages that the method includes simple and convenient steps and can be practically put into production, and raw materials for the ropinirole hydrochloride are simple and are easily available.

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 %).