720656-64-4

Basic information

• Product Name: 2-(2-N,N-DIPROPYLAMINOETHYL)-6-NITROPHENYL ACETIC ACID
• Synonyms: 2-(2-N,N-DIPROPYLAMINOETHYL)-6-NITROPHENYL ACETIC ACID;2-[2-(Dipropylamino)ethyl]-6-nitrophenylacetic acid
• CAS NO: 720656-64-4
• Molecular Formula: C₁₆H₂₄N₂O₄
• Molecular Weight: 308.37
• Mol File: 720656-64-4.mol

Chemical Properties

• Boiling Point: 454.6 °C at 760 mmHg
• Flash Point: 228.7 °C
• Appearance: /
• Density: 1.151 g/cm³
• Vapor Pressure: 4.68E-09mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: 2-(2-N,N-DIPROPYLAMINOETHYL)-6-NITROPHENYL ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-N,N-DIPROPYLAMINOETHYL)-6-NITROPHENYL ACETIC ACID(720656-64-4)
• EPA Substance Registry System: 2-(2-N,N-DIPROPYLAMINOETHYL)-6-NITROPHENYL ACETIC ACID(720656-64-4)

Safety Data

• Hazardous Substances Data: 720656-64-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-N,N-Dipropylaminoethyl)-6-nitrophenyl acetic acid is used as an intermediate in the synthesis of pharmaceuticals for its potential to contribute to the development of new drugs. Its nitro group serves as a pharmacophore, a key structural element in drug design, while the dipropylaminoethyl group is believed to enhance medicinal properties.
Used in Drug Development:
In drug development, 2-(2-N,N-Dipropylaminoethyl)-6-nitrophenyl acetic acid is utilized as a potential drug molecule. Ongoing research is focused on exploring its therapeutic applications, leveraging its unique structural components to target specific biological pathways or conditions.

InChI:InChI=1/C16H24N2O4/c1-3-9-17(10-4-2)11-8-13-6-5-7-15(18(21)22)14(13)12-16(19)20/h5-7H,3-4,8-12H2,1-2H3,(H,19,20)

Upstream product

• 91374-20-8 ropinirole hydrochloride 
• 91374-22-0 2-(2-methyl-3-nitro-phenyl)-N,N-di-n-propylacetamide 
• 91374-23-1 1-(2-dipropylaminoethyl)-2-methyl-3-nitrobenzene 
• 101566-00-1 2-methyl-3-nitrophenylethanoyl chloride 
• 23876-15-5 2-(3-nitro-2-methylphenyl)acetic acid 
• 97351-95-6 <2-nitro-6-<2-(N,N-di-n-propylamino)ethyl>phenyl>pyruvic acid 

Downstream Products

• 91374-21-9 Ropinirole 

Relevant articles and documents

Development and validation of Ropinirole hydrochloride and its related compounds by UPLC in API and pharmaceutical dosage forms

A novel stability-indicating gradient reverse phase ultra performance liquid chromatographic (RP-UPLC) method was developed for the determination of purity of Ropinirole in presence of its impurities and forced degradation products. The method was developed using Waters Aquity BEH 100 mm, 2.1 mm, 1.7 μm C-8 column with mobile phase containing a gradient mixture of solvent A and B. The eluted compounds were monitored at 250 nm. The run time was within 4.5 min which Ropinirole and its four impurities were well separated. Ropinirole was subjected to the stress conditions of oxidative, acid, base, hydrolytic, thermal and photolytic degradation. Ropinirole was found to degrade significantly in oxidative and base stress conditions and stable in acid, water, hydrolytic and photolytic degradation conditions. The degradation products were well resolved from main peak and its impurities, thus proved the stability indicating power of the method. The developed method was validated as per International Conference on Harmonization (ICH) guidelines with respect to specificity, linearity, limit of detection, limit of quantification, accuracy, precision and robustness. This method was also suitable for the assay determination of Ropinirole in pharmaceutical dosage forms and dissolution studies.

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 %).

Syntheses and in Vitro Evaluation of 4-(2-Aminoethyl)-2(3H)-indolones and Related Compounds as Peripheral Prejunctional Dopamine Receptor Agonists

A series of (β-aminoethyl)indolones and related compounds was synthesized and evaluated in vitro as peripheral prejunctional dopaminergic agonists in the field-stimulated isolated perfused rabbit ear artery. 4--7-hydroxy-2(3H)-indolone (26) was the most potent compound (ED50 = 2 +/- 0.3 nM) tested, while the related secondary amine 24 and the des-OH derivatives 28 and 34 were only slightly less potent. 4-Methoxy-benzeneethanamine and 2-methyl-3-nitrophenylacetic acid were employed as starting materials for the synthesis of the 4-(β-aminoethyl)indolones.The ring-opened 3-acylamino analogues 46 and 47 were prepared via nitration of the phenethylamine 43 derived from 4-methoxyphenylacetic acid.The inactive isomeric indolones 38, 39, and 41 were derived from 4-nitrobenzeneethanamine and from indolone-6-acetic acid (13).