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

Chemical Properties

White or almost white powder

Uses

Methyl 4-Amino-5-chloro-2-methoxybenzoate is used in preparation of phenoxymethylpyridine derivatives as immunomodulators.

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

• 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 
• 4093-28-1 methyl 4-acetamido-2-hydroxybenzoate 
• 4235-43-2 4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester 

Downstream Products

• 1132683-11-4 (S)-6-{2-[(4-amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-yl}-hexanoic acid ethyl ester 
• 1132683-37-4 (R)-6-(2-((4-amino-5-chloro-2-ethoxy-benzoylamino)-methyl)-morpholino)-hexanoic acid ethyl ester 
• 1132682-95-1 (R)-quinuclidin-3-yl 6-((R)-2-((4-amino-5-chloro-2-ethoxybenzamido)methyl)morpholino)hexanoate 
• 1132683-07-8 (S)-5-{2-[(4-amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-yl}-pentanoic acid ethyl ester 
• 1132683-33-0 (R)-5-{2-[(4-amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-yl}-pentanoic acid ethyl ester 
• 1132683-34-1 (R)-4-{2-[(4-amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-yl}-butyric acid ethyl ester 
• 1388193-51-8 Br^(1-)*C₃₂H₃₆ClN₂O₇⁽¹⁺⁾ 
• 1388193-68-7 C₁₁H₁₃BrClNO₃ 
• 1388193-69-8 C₁₂H₁₅BrClNO₃ 
• 124257-25-6 4-amino-N-<(4-benzyl-3,4,5,6-tetrahydro-2H-1,4-thiazin-2-yl)methyl>-5-chloro-2-ethoxybenzamide 

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.