108282-38-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Ethoxy-4-amino-5-chlorobenzoic acid is used as a key intermediate in the synthesis of phenoxymethylpyridine derivatives, which are known for their immunomodulatory properties. These derivatives can be employed in the development of drugs targeting various immune system-related conditions, making 2-Ethoxy-4-amino-5-chlorobenzoic acid a valuable asset in the pharmaceutical sector.
Used in Chemical Synthesis:
Due to its unique chemical structure, 2-Ethoxy-4-amino-5-chlorobenzoic acid can be utilized as a building block in the synthesis of various other organic compounds. Its versatility in chemical reactions allows it to be used in the creation of a wide range of products, from pharmaceuticals to specialty chemicals.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 19, p. 1696, 1971 DOI: 10.1248/cpb.19.1696

InChI:InChI=1/C9H10ClNO3/c1-2-14-8-4-7(11)6(10)3-5(8)9(12)13/h3-4H,2,11H2,1H3,(H,12,13)

Upstream product

• 4093-28-1 methyl 4-acetamido-2-hydroxybenzoate 
• 133-10-8 sodium p-aminosalicylate 
• 36467-52-4 2-hydroxy-4-(1,3-dioxoisoindolin-2-yl)benzoic acid 
• 4136-97-4 methyl 4-aminosalicylate 
• 65-49-6 4-Aminosalicylic acid 
• 59-06-3 methyl 4-acetamido-2-ethoxybenzoate 
• 4235-43-2 4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester 

Downstream Products

• 112914-03-1 methyl 4-amino-5-chloro-2-ethoxybenzoate 
• 112885-33-3 4-amino-N-<(4-benzyl-2-morpholinyl)methyl>-5-chloro-2-ethoxybenzamide 
• 126645-69-0 4-amino-N-[2-(4-benzyl-2-morpholinyl)ethyl]-5-chloro-2-ethoxybenzamide 
• 126645-71-4 4-Amino-N-[3-(4-benzyl-morpholin-2-yl)-propyl]-5-chloro-2-ethoxy-benzamide 
• 112886-42-7 4-Amino-5-chloro-2-ethoxy-N-[4-(3-phenyl-propyl)-morpholin-2-ylmethyl]-benzamide 
• 112886-40-5 4-Amino-5-chloro-2-ethoxy-N-[4-(4-phenyl-butyl)-morpholin-2-ylmethyl]-benzamide 
• 112886-38-1 4-Amino-5-chloro-2-ethoxy-N-[4-(1-phenyl-ethyl)-morpholin-2-ylmethyl]-benzamide 
• 112886-58-5 4-Amino-5-chloro-2-ethoxy-N-[4-(2-fluoro-benzyl)-morpholin-2-ylmethyl]-benzamide 
• 112885-41-3 mosapride 
• 112886-45-0 4-Amino-5-chloro-N-[4-(3-cyano-benzyl)-morpholin-2-ylmethyl]-2-ethoxy-benzamide 
• 131322-30-0 4-{2-[(4-Amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-ylmethyl}-benzoic acid methyl ester 
• 112886-49-4 4-Amino-5-chloro-2-ethoxy-N-[4-(3-trifluoromethyl-benzyl)-morpholin-2-ylmethyl]-benzamide 
• 112886-44-9 4-Amino-5-chloro-N-[4-(4-chloro-2-nitro-benzyl)-morpholin-2-ylmethyl]-2-ethoxy-benzamide 
• 112886-50-7 4-Amino-5-chloro-2-ethoxy-N-(4-pentafluorophenylmethyl-morpholin-2-ylmethyl)-benzamide 

Relevant academic research and scientific papers

Method for preparing mosapride intermediate

The invention provides a method for preparing a mosapride intermediate, and concretely relates to a method for preparing a key mosapride intermediate 2-ethoxy-4-amino-chlorobenzoic acid. The method ischaracterized in that the intermediate is prepared from sodium 4-aminosalicylate by four steps of N-carbethoxyphthalimide acylation, ethyl bromide bisethylation, N-chlorosuccinimide chlorination andalcoholic hydrazine hydrate solution deprotection and hydrolysis. The method which improves the synthesis process of the intermediate greatly improves the yield of the intermediate, shortens the reaction time and effectively reduces the production cost.

Synthesis and biological evaluation of berberine derivatives as IBS modulator

Irritable bowel syndrome is the most common functional gastrointestinal disorder characterized by chronic abdominal pain or discomfort in association with a change in bowel habit. 5-HT receptor modulators have been developed as IBS therapeutic agents and proved to be effective in the treatment of the disease. In this letter, 12 berberine derivatives were designed and synthesized as 5-HT receptor modulators. Preliminary biological tests suggested that the new compounds exhibited promising activity for IBS therapy.

Synthesis and structure-activity relationship of 3-substituted benzamide, benzo[b]furan-7-carboxamide, 2,3-dihydrobenzo[b]furan-7- carboxamide, and indole-5-carboxamide derivatives as selective serotonin 5- HT4 receptor agonists

The title compounds (6-9) were prepared and evaluated for serotonin 5- HT4 agonistic activity in in vitro tests. Introducing a propyl or allyl group at the 3-position of benzamide caused only a slight enhancement of agonistic activity. Construction of the benzo[b']furan skeleton and 2,3- dihydrobenzo[b]furan skeleton caused a significant enhancement of the activity. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2- methylbenzo[b]furan-7-carboxamide (7b) hemifumarate was as potent as cisapride. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3- dihydro-2-methylbenzo[b]furan-7-carboxamide (8a) hemifumarate, 4-amino-N-[2- (1-azabicyclo [3.3.0]octan-5-yl)ethyl]5-chloro-2,3-dihydro-2- ethylbenzo[b]furan-7-carboxamide (8c) hemifumarate, and 4-amino-N-]2-(1- azabicyclo[3.3.0]octan-5-yl]-5-chloro-2,3-dihydro-2,3-dimethylhenzo[b]furan- 7-carboxamide (8d) hemifumarate were more potent than cisapride. Furthermore, 8a hemifumarate was free from dopamine D1, D2, serotonin 5-HT1, 5-HT2 and muscarine M1, M2 receptor binding activity in the in vitro tests. On the other hand, construction of the indole skeleton caused a remarkable decrease in activity.

Novel benzamides as selective and potent gastrokinetic agents. 2.1 Synthesis and structure-activity relationships of 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl] benzamide citrate (AS-4370) and related compounds

The title compounds (19-55) with a 4-substituted 2-(aminomethyl)morpholine group were prepared and evaluated for the gastrokinetic activity by determining their effect on gastric emptying of phenol red semisolid meal in rats. Introduction of chloro, fluoro, and trifluoromethyl groups to the benzyl group of the parent compounds 1a and 1b enhanced the activity. Among compounds tested, 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl] methyl]benzamide (23b) showed the most potent gastric emptying activity (effects on phenol red semisolid meal in rats and mice, and on resin pellets solid meal in rats). The gastrokinetic activity of 23b citrate (AS-4370) compared very favorably with that of cisapride and was higher than that of metoclopramide. In contrast to metoclopramide and cisapride, AS-4370 was free from dopamine D2 receptor antagonistic activity in both in vitro ([3H]spiperone binding) and in vivo (apomorphine-induced emesis in dogs) tests.