55860-23-6

Usage

Uses

Used in Pharmaceutical Synthesis:
3-CHLORO-N-(2-METHOXYPHENYL)PROPANAMIDE is used as an intermediate in the synthesis of 8-Hydroxy-3,4-dihydro-2(1H)-quinolinone (H941405), which is involved in the studies of salvianolic acid B metabolites. This application highlights its importance in the development of novel therapeutic agents and the understanding of their metabolic pathways.
Used in the Synthesis of Aripiprazole Impurity 5:
In the pharmaceutical industry, 3-CHLORO-N-(2-METHOXYPHENYL)PROPANAMIDE is also utilized in the synthesis of Aripiprazole Impurity 5. Aripiprazole is an atypical antipsychotic drug used to treat various psychiatric disorders, such as schizophrenia and bipolar disorder. The synthesis of its impurities, including Impurity 5, is essential for quality control and safety assessments of the final drug product.

InChI:InChI=1/C10H12ClNO2/c1-14-9-5-3-2-4-8(9)12-10(13)6-7-11/h2-5H,6-7H2,1H3,(H,12,13)

Upstream product

• 90-04-0 2-methoxy-phenylamine 
• 625-36-5 2-chloropropionyl chloride 

Downstream Products

• 53899-19-7 3,4-dihydro-8-methoxy-2(1H)-quinolinone 

Relevant academic research and scientific papers

Synthesis of novel 3,4-dihydroquinolin-2(1H)-one guanidines as potential antihypertensive agents

Hydroxy-3,4-dihydroquinolin-2(1H)-ones (4a-c) were synthesized by intramolecular Friedel Craft alkylation of N-(methoxyphenyl)-3- chloropropionamides (3a-c), obtained by acylation of anisidine with chloropropionyl chloride. The hydroxy-3,4-dihydro quinolin-2(1H)- ones (4a-c) were treated with various dibromo alkanes under phase transfer catalyst conditions at room temperature to give bromoalkyloxy- 3,4-dihydroquinolin-2(1H)- ones (5a-l) which on further reaction with guanidine hydrochloride in dimethyl formamide afforded N-{4- [(2-oxo-1,2,3,4-tetrahydroquinolin-5-yl)oxy]alkyl} guanidines (6a-l). These compounds were synthesized as potential antihypertensive agents.

The synthesis and anticonvulsant activity of some omega-phthalimido-N-phenylacetamide and propionamide derivatives.

In this study, by combining anilide and N', N'-phthaloylglycinamide pharmacophores which are known to produce potent anticonvulsant compounds, sixteen omega-phthalimido-N-phenylacetamide and propionamide derivatives bearing substituents at positions 2 or 2, 6 on N-phenyl ring have been synthesized. The structural confirmation of the title compounds was achieved by interpretation of spectral and analytical data. The anticonvulsant activity of the title compounds was determined against maximal electroshock seizure at 100 mg/kg dose level in mice. The preliminary screening results indicated that omega-phthalimido-N-phenylacetamide and propionamide nuclei have pronounced anticonvulsant activity against maximal electroshock seizure.

Synthesis and anticonvulsant activity of some ω-(1H-1-imidazolyl)-N- phenylalkanoic acid amide derivatives

In this study, 15 ω-(1H-imidazol-1-yl)-N-phenylacetamide, propionamide and butyramide derivatives having methoxyl, methyl, nitro and chloro in ortho position of N-phenyl ring or without any substituent have been realized by two-step synthesis. Their antic

Aluminium chloride-catalyzed intermolecular vs intramolecular friedel-crafts reaction of acrylanilides and 3-chloropropanamides

3-Phenylpropionanilide (4a) is obtained in a yield of 89% from acrylanilide by the treatment with AlCl3/ benzene, compared with a yield of 39% by the 1,4-conjugate addition of phenyllithium. The formation of 4a indicated that an intermolecular Friedel-Crafts reaction occurred, rather than the relatively more facile intramolecular ring cyclization, and provided a more efficient route than a conjugate addition of phenyllithium for the preparation of 3-phenylpropionanilide and its derivatives. Although the methoxy group is an activator of the nucleophilic substitution, introduction of a methoxy substituent at N-phenyl did not increase the competitive capability of the intramolecular cyclization because of AlCl3-catalyzed demethylation to form the ArOAlCl2 complex which decreased the availability of the π-electron in the N-phenyl aromatic system.