139122-19-3

Basic information

• Product Name: 1,3-Dihydro-4-(2-hydroxyethyl)-2H-indole-2-one
• Synonyms: 4-(2'-HYDROXYETHYL)-1,3-DIHYDRO-2H-INDOLE-2-ONE;4-(2-Hydroxyethyl)-2-oxoindole;Ropinirole Intermediate 5;2H-INDOL-2-ONE, 1,3-DIHYDRO-4-(2-HYDROXYETHYL)-;4-(2-YDROXYETHYL)OXYINDOLE;1,3-dihydro-4-(2-hydroxyethyl)-2H-indol-2-one;4-(2’-Hydroxylethyl)-1,3-di- hydro-2H-Indol-2-one;1,3-Dihydro-4-(2-hydroxyethyl)-2H-indole-2-one
• CAS NO: 139122-19-3
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.19984
• EINECS: 1312995-182-4
• Product Categories: Pharmaceutical material and intermeidates;Indoles;Aromatics Compounds;Aromatics;Heterocycles;Indole Derivatives
• Mol File: 139122-19-3.mol

Chemical Properties

• Melting Point: 148-150°C
• Boiling Point: 390.019 °C at 760 mmHg
• Flash Point: 189.677 °C
• Appearance: Yellow solid
• Density: 1.253 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.08±0.20(Predicted)
• CAS DataBase Reference: 1,3-Dihydro-4-(2-hydroxyethyl)-2H-indole-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dihydro-4-(2-hydroxyethyl)-2H-indole-2-one(139122-19-3)
• EPA Substance Registry System: 1,3-Dihydro-4-(2-hydroxyethyl)-2H-indole-2-one(139122-19-3)

Safety Data

• Hazard Codes: Xi
• Statements: 42/43
• Safety Statements: 36/37
• Hazardous Substances Data: 139122-19-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 139122-19-3 differently. You can refer to the following data:
1. Ropinirole Intermediate
2. Ropinirole Intermediate.

InChI:InChI=1/C10H11NO2/c12-5-4-7-2-1-3-9-8(7)6-10(13)11-9/h1-3,12H,4-6H2,(H,11,13)

Upstream product

• 168476-61-7 4-(2-acetoxyethyl)-1,3-dihydro-2H-indolin-2-one 
• 139122-18-2 4-(2-benzoyloxyethyl)-1,3-dihydro-2H-indolin-2-one 
• 493-05-0 isochromane 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 95033-78-6 1-hydroxyisochroman 
• 120427-94-3 2-(2-bromoethyl)-β-nitrostyrene 
• 168476-58-2 2-[2-(chloromethyl)phenyl]ethylbenzoate 
• 139122-15-9 benzoic acid (2-formyl)phenethyl ester 
• 139122-17-1 4-[2-(benzoyloxy)ethyl]-3-chloro-1,3-dihydro-2H-indolin-2-one 
• 855382-76-2 2-(2-methyl-3-nitrophenyl)ethyl alcohol 
• 1426679-27-7 2-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]acetic acid 
• 23876-15-5 2-(3-nitro-2-methylphenyl)acetic acid 
• 1426679-26-6 1-[(2-methyl-3-nitrophenethyloxy)methyl]benzene 
• 1441070-77-4 ethyl 3-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]-2-oxopropanoate 

Downstream Products

• 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 
• 91374-21-9 Ropinirole 
• 120427-93-2 4-ethylenyl-1,3-dihydro-2H-indol-2-one 
• 295799-05-2 phenyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester 
• 295799-03-0 phenyl-thiocarbamic acid O-[2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl]ester 
• 295799-11-0 benzene sulfonyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester 
• 295799-07-4 tert-butyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester 
• 295798-87-7 4-[2-(2-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one 
• 295798-85-5 4-[2-(3-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one 
• 120427-96-5 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one 

Relevant articles and documents

A new scalable route to 4-(2-hydroxyethyl)-1,3-dihydro-2 H-indol-2-one: A key intermediate for ropinirole hydrochloride

A new and efficient manufacturing technology is disclosed in the present work for the preparation of 4-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one, which is a key intermediate for ropinirole hydrochloride. The whole process gives the target molecule in 71% overall yield with 99% purity. In the final step, a novel nitro reduction/ring-closing/debenzylation takes place in one pot. All the intermediates can be used directly for the next step without purification in this process.

A process for preparing 4 - (2 - hydroxyethyl) - 1, 3 - dihydro - 2H - indole -2 - one of the new method

The invention discloses a novel method for preparing a ropinirole hydrochloride key intermediate 4-(2-ethoxy)-1,3-dihydro-2H-indole-2-ketone (I). The reaction process comprises the following steps of: carrying out reduction reaction on 2-methyl-3-nitrobenzene acetic acid (III) to generate 2-methyl-3-nitrobenzene ethanol (IV); protecting the hydroxyl of the compound (IV) to generate 2-methyl-3-(2-alkoxy ethyl) nitrobenzene (V); reacting the compound (V) with diethyl oxalate to generate a 2-nitro-6-(2-alkoxy ethyl)-phenyl acetyl formic acid compound (VI); reacting the compound (VI) with hydrogen peroxide to generate 2-nitro-6-(2-alkoxy ethyl)-phenylacetic acid (VII); and carrying out oxidation reaction on the compound (VII) to obtain 4-(2-ethoxy)-1,3-dihydro-2H-indole-2-ketone (I).

Design, synthesis, and biological evaluation of structurally constrained hybrid analogues containing ropinirole moiety as a novel class of potent and selective dopamine D3 receptor ligands

Two series of hybrid analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined (using the method of radioligand binding assay). Compared to comparator agent BP897, compounds 2a and 2c were found to demonstrate a considerable binding affinity and selectivity for D3 receptor, and especially compound 2h was similarly potent and more selective D3R ligand than BP897, a positive reference. Thus, they may provide valuable information for the discovery and development of highly potent dopamine D3 receptor ligands with outstanding selectivity.

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.

Indoline-2-ketone D3 receptor ligand and preparation method and application thereof

The invention discloses an indoline-2-ketone D3 receptor ligand, which is a compound as shown in the formula I or pharmaceutical salt thereof, wherein n=2 or 3; R represents H, 4-CH3, 2,3-diCH3, 2-CH3, 4-OCF3, 3-OCH3, 3,4-diCH3 or 4-Cl. In comparison with the prior art, the compound has a strong activity to a dopamine D3 receptor, is used in treating or preventing central nervous and metal diseases such as schizophrenia, Parkinson's disease, drug dependence and relapse, etc., can be used in neuroprotection, and is used as a tool drug for researching D3 receptor structure, function and diseases related to D3 receptor dysfunction.

Improved preparation method for ropinirole hydrochloride

The invention discloses an improved preparation method for ropinirole hydrochloride. The ropinirole hydrochloride is a compound shown in the formula I and is prepared through a series of reactions with 2-phenylethanol as a starting raw material. Compared with the prior art, according to the method, raw materials are cheap and easy to get, reaction conditions are mild, technological operation is easy, control is easy, the product is high in total yield and purity, and the method is suitable for industrial production.

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 %).

Hexahydro-cyclohepta-pyrrole oxindole as potent kinase inhibitors

The present invention is directed to a class indolinone compounds, hexahydro-cyclohepta-pyrrole oxindoles, which are useful as protein kinase inhibitors.

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.