139122-18-2

Basic information

• Product Name: 2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydro-
• Synonyms: 2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydro-;4-[2-(Benzoyloxy)ethyl]-1,3-dihydro-2H-indol-2-one;2-(2-oxoindolin-4-yl)ethyl benzoate
• CAS NO: 139122-18-2
• Molecular Formula: C₁₇H₁₅NO₃
• Molecular Weight: 281.3059
• Mol File: 139122-18-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 493.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.243±0.06 g/cm3(Predicted)
• Solubility: DCM, Ethyl Acetate, Methanol
• PKA: 14.05±0.20(Predicted)
• CAS DataBase Reference: 2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydro-(139122-18-2)
• EPA Substance Registry System: 2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydro-(139122-18-2)

Safety Data

• Hazardous Substances Data: 139122-18-2(Hazardous Substances Data)

Usage

Uses

4-[2-(Benzoyloxy)ethyl]-1,3-dihydro-2H-indol-2-one is an useful intermediate in the preparation of both Dopamine receptor agonists and protein kinase inhibitors.

Upstream product

• 60-12-8 2-phenylethanol 
• 139122-16-0 benzoic acid (2-(2-nitroethenyl))phenethyl ester 
• 98-88-4 benzoyl chloride 
• 139122-15-9 benzoic acid (2-formyl)phenethyl ester 
• 168476-58-2 2-[2-(chloromethyl)phenyl]ethylbenzoate 
• 493-05-0 isochromane 
• 139122-17-1 4-[2-(benzoyloxy)ethyl]-3-chloro-1,3-dihydro-2H-indolin-2-one 

Downstream Products

• 91374-21-9 Ropinirole 
• 120427-93-2 4-ethylenyl-1,3-dihydro-2H-indol-2-one 
• 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 
• 120427-96-5 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one 
• 91374-20-8 ropinirole hydrochloride 
• 139122-19-3 4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one 

Relevant articles and documents

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.

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.

Process

There is disclosed a process for the preparation of a compound of structure (I) STR1 in which n is 1 to 3 and each group R is hydrogen or C1-4 alkyl, which comprises, reaction of compound of structure (II) STR2 (prepared by esterifying the hydroxyl compound) in which R1 is C1-4 alkyl, phenyl or substituted phenyl and n is 1 to 3, with an amine HNR2 in which R is as described for structure (I), and optionally thereafter forming a salt. Intermediates are also disclosed.