108282-38-8

Basic information

• Product Name: 2-Ethoxy-4-amino-5-chlorobenzoic acid
• Synonyms: 2-ETHOXY-4-AMINO-5-CHLOROBENZOIC ACID;4-AMINO-5-CHLORO-2-ETHOXYBENZOIC ACID;METHYL 4-AMINO-5-CHLORO-2-METHOXYBENZOATE;4-Amino-5-Chloro-2-Ethoxy Benzoic Acid 2-Ethoxy-4-Amino-5-Chlorobenzoic Acid;3-Carbomethoxy-1-chloro-4-methoxyanaline;4-amino-5-chloro-2-ethoxy-benzoic acid (intermediate of mosapride citrate );Benzoic acid,4-aMino-5-chloro-2-ethoxy-;Mosapride Impurity I
• CAS NO: 108282-38-8
• Molecular Formula: C₉H₁₀ClNO₃
• Molecular Weight: 215.63
• EINECS: 1592732-453-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;(intermediate of mosapride citrate );Aromatics Compounds;Pharmaceutical Intermediates
• Mol File: 108282-38-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 165-169°C
• Boiling Point: 377.708 °C at 760 mmHg
• Flash Point: 182.232 °C
• Appearance: white crystal powder
• Density: 1.376 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.50±0.10(Predicted)
• CAS DataBase Reference: 2-Ethoxy-4-amino-5-chlorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxy-4-amino-5-chlorobenzoic acid(108282-38-8)
• EPA Substance Registry System: 2-Ethoxy-4-amino-5-chlorobenzoic acid(108282-38-8)

Safety Data

• Hazardous Substances Data: 108282-38-8(Hazardous Substances Data)

Usage

Description

2-Ethoxy-4-amino-5-chlorobenzoic acid is an organic compound characterized by its chemical structure that features an ethoxy group at the 2nd position, an amino group at the 4th position, and a chlorine atom at the 5th position on a benzoic acid backbone. It is a white or almost white powder with specific chemical properties that make it suitable for various applications in different industries.

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 this compound 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

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

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 articles and documents

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 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.