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

Description

2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydrois a chemical compound with the molecular formula C16H13NO3. It is an organic compound that belongs to the indole family, which is known for its diverse range of biological activities and applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydrois used as an intermediate in the synthesis of various pharmaceutical compounds. Its primary applications include the preparation of Dopamine receptor agonists and protein kinase inhibitors.
As a Dopamine Receptor Agonist:
2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydrois used as a key intermediate in the development of Dopamine receptor agonists. These agonists are essential in the treatment of various neurological and psychiatric disorders, such as Parkinson's disease, schizophrenia, and attention deficit hyperactivity disorder (ADHD). Dopamine receptor agonists work by mimicking the action of dopamine, a neurotransmitter that plays a crucial role in regulating movement, mood, and cognition.
As a Protein Kinase Inhibitor:
2H-Indol-2-one, 4-[2-(benzoyloxy)ethyl]-1,3-dihydrois also utilized in the synthesis of protein kinase inhibitors. Protein kinases are enzymes that play a significant role in cellular signaling and regulation, and their dysregulation has been implicated in various diseases, including cancer, diabetes, and autoimmune disorders. Protein kinase inhibitors are designed to block the activity of these enzymes, thereby disrupting the signaling pathways that contribute to disease progression. These inhibitors have potential applications in the development of targeted therapies for cancer and other diseases.

Upstream product

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

Downstream Products

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