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
• Article Data: 11

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 
• 120427-96-5 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one 
• 120427-94-3 2-(2-bromoethyl)-β-nitrostyrene 
• 120427-95-4 4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one 
• 168476-58-2 2-[2-(chloromethyl)phenyl]ethylbenzoate 
• 139122-15-9 benzoic acid (2-formyl)phenethyl ester 
• 168476-57-1 4-(2-acetoxyethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one 
• 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 

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.

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.

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.