Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Base Information

• Chemical Name: Methyl 4-acetamido-5-chloro-2-methoxybenzoate
• CAS No.: 4093-31-6
• Molecular Formula: C11H12ClNO4
• Molecular Weight: 257.674
• Hs Code.: 29242990
• European Community (EC) Number: 223-840-1
• UNII: 3D7Z5O4UXA
• DSSTox Substance ID: DTXSID6057740
• Nikkaji Number: J61.603F
• Wikidata: Q27257067
• ChEMBL ID: CHEMBL3561753
• Mol file: 4093-31-6.mol

Synonyms:Methyl 4-acetamido-5-chloro-2-methoxybenzoate;4093-31-6;Methyl 4-acetamido-5-chloro-o-anisate;Benzoic acid, 4-(acetylamino)-5-chloro-2-methoxy-, methyl ester;MFCD00048191;UNII-3D7Z5O4UXA;methyl 4-(acetylamino)-5-chloro-2-methoxybenzoate;3D7Z5O4UXA;DTXSID6057740;methyl 2-methoxy-4-acetamido-5-chlorobenzoate;EINECS 223-840-1;EC 223-840-1;methyl 2-methoxy-4-acetylamino-5-chlorobenzoate;Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate;4-acetamido-5-chloro-2-methoxybenzoic acid methyl ester;methyl 5-chloro-4-acetamido-2-methoxybenzoate;Oprea1_093629;SCHEMBL130152;CHEMBL3561753;DTXCID3031529;BCP30994;Tox21_113842;AC7971;AKOS002952816;NCGC00253723-01;AC-14848;AS-12356;SY034797;CAS-4093-31-6;CS-0128349;FT-0617372;Methyl4-acetamido-5-chloro-2-methoxybenzoate;Methyl-4-acetamido-5-chloro-2-methoxybenzoate;methyl 4-acetamido-5-chloro-2-methoxy-benzoate;METOCLOPRAMIDE IMPURITY B [EP IMPURITY];SR-01000944779;SR-01000944779-1;W-106329;Methyl 4-acetamido-5-chloro-2-methoxybenzoate, 99%;Q27257067;methyl 4-(acetylamino)-5-chloro-2-(methyloxy)benzoate;METHYL-4-ACETYLAMINO-5-CHLORO-2-METHOXYBENZOATE;4-Acetylamino-5-chloro-2-methoxy-benzoic acid methyl ester;2-Methoxy-4-(acetylamino)-5-chlorobenzoic acid methyl ester;4-(N-acetylamino)-5-chloro-2-methoxybenzoic acid, methyl ester

Chemical Property of Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Chemical Property:

• Appearance/Colour: white to light beige fine crystalline powder
• Vapor Pressure: 5.99E-08mmHg at 25°C
• Melting Point: 153-156 °C
• Refractive Index: 1.564
• Boiling Point: 440.2 °C at 760 mmHg
• PKA: 13.16±0.70(Predicted)
• Flash Point: 220 °C
• PSA: 64.63000
• Density: 1.312 g/cm³
• LogP: 2.16660
• Storage Temp.: 2-8°C
• Water Solubility.: 1.14g/L at 25℃
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 257.0454856
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-Acetylamino-5-chloro-2-methoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=C(C=C(C(=C1)OC)C(=O)OC)Cl
• Uses: Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate is an biotransformed metabolite of Metoclopramide (M338685), an dopamine D2 receptor antagonist and antiemetic agent. Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate (Metoclopramide EP Impurity B; Metoclopramide USP Related Compound B) is an biotransformed metabolite of Metoclopramide (M338685), an dopamine D2 receptor antagonist and antiemetic agent.

Technology Process of Methyl 4-acetamido-5-chloro-2-methoxybenzoate

There total 11 articles about Methyl 4-acetamido-5-chloro-2-methoxybenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.3%

methyl 4-(acetylamino)-o-anisate (4093-29-2) → methyl 2-methoxy 4-acetamido 5-chloro benzoate (4093-31-6)

Guidance literature:

With N-chloro-succinimide; In N,N-dimethyl-formamide; at 40 - 65 ℃; for 9h; Temperature;

Reference yield: 80.0%

methyl 4-amino-5-chloro-2-methoxybenzoate (20896-27-9) + acetic anhydride (108-24-7) → methyl 2-methoxy 4-acetamido 5-chloro benzoate (4093-31-6)

Guidance literature:

With acetic acid; at 50 ℃; for 5h;

Reference yield: 67.0%

methyl 4-amino-5-chloro-2-methoxybenzoate (20896-27-9) + acetic acid (64-19-7,77671-22-8) + acetyl chloride (75-36-5) → methyl 2-methoxy 4-acetamido 5-chloro benzoate (4093-31-6)

Guidance literature:

for 12h; Reflux;

upstream raw materials:

methyl 4-(acetylamino)-o-anisate

Methyl 4-amino-2-methoxybenzoate

methyl 4-amino-5-chloro-2-methoxybenzoate

6-amino-5-nitro-pyridine-2-carboxylic acid methyl ester

Downstream raw materials:

N-(2-Amino-6-chloro-4-formyl-3-methoxy-phenyl)-acetamide

N-(6-Chloro-4-hydroxymethyl-3-methoxy-2-nitro-phenyl)-acetamide

N-(6-Chloro-4-formyl-3-methoxy-2-nitro-phenyl)-acetamide

2-(3,4-diamino-5-chloro-2-methoxyphenyl)-5-methyl-4-(3-pyridyl)imidazole

Refernces

• 1、 -. "As neuroprotective agents of pharmaceutical compounds". . . Retrieved 2019/06/26.
• 2、 Deng, Xin,Zhao, Xinxin,Han, Jing,Wang, Jingjie,Huang, Wenlong,Qian, Hai,Ge, Liang. "Synthesis and biological evaluation of berberine derivatives as IBS modulator". scheme or table. p. 489 - 493. Retrieved 2012/08/29.