2-Anilino-5-methoxybenzoic acid

Base Information

• Chemical Name: 2-Anilino-5-methoxybenzoic acid
• CAS No.: 89224-95-3
• Molecular Formula: C14H13NO3
• Molecular Weight: 243.262
• DSSTox Substance ID: DTXSID60500738
• Wikidata: Q82352614
• Mol file: 89224-95-3.mol

Synonyms:89224-95-3;2-Anilino-5-methoxybenzoic acid;SCHEMBL10652538;DTXSID60500738;JNJNRHBPVSHRQY-UHFFFAOYSA-N;5-methoxy-2-(phenylamino)benzoic acid

Chemical Property of 2-Anilino-5-methoxybenzoic acid

Chemical Property:

• PSA: 58.56000
• LogP: 3.21000
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 243.08954328
• Heavy Atom Count: 18
• Complexity: 276

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)NC2=CC=CC=C2)C(=O)O

Technology Process of 2-Anilino-5-methoxybenzoic acid

There total 6 articles about 2-Anilino-5-methoxybenzoic acid 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: 55.0%

potassium 2-chloro-5-methoxybenzoate (95216-58-3) + aniline (62-53-3) → 5-methoxy-2-(phenylamino)benzoic acid (89224-95-3)

Guidance literature:

With copper; In i-Amyl alcohol; for 21h; Heating;

DOI:10.1021/jm50001a006

Reference yield: 49.0%

aniline (62-53-3) + 2-bromo-5-methoxy-benzoic acid (22921-68-2) → 5-methoxy-2-(phenylamino)benzoic acid (89224-95-3)

Guidance literature:

With copper; potassium carbonate; In N,N-dimethyl-formamide; at 150 ℃; for 2h;

DOI:10.1002/cmdc.200900454

Reference yield:

2-iodo-5-methoxybenzoic acid (54413-93-3) + aniline (62-53-3) → 5-methoxy-2-(phenylamino)benzoic acid (89224-95-3)

Guidance literature:

With copper diacetate; sodium acetate; In water; Reflux;

DOI:10.1021/ol400371h

upstream raw materials:

2-chloro-5-methoxybenzoic acid

aniline

2-bromo-5-methoxy-benzoic acid

potassium 2-chloro-5-methoxybenzoate

Downstream raw materials:

2-methoxy-9(10H)-acridinone

N-(4-methoxyphenyl)phenylamine

C₁₆H₁₇NO₃

5-methoxy-2-(methyl(phenyl)amino)benzaldehyde

Refernces

• 1、 Chang, Jia-jia,Hou, Shi,Lan, Xiu-juan,Li, Song,Li, Wei,Sun, Wei,Xiao, Jun-hai,Yan, Xin-lin,Yang, Xiao-hong. "Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists". . . Retrieved 2020/01/09.
• 2、 Liu, Le,Du, Liang,Zhang-Negrerie,Du, Yunfei. "NIS-mediated intramolecular oxidative α-functionalization of tertiary amines: Transition metal-free synthesis of 1,2-dihydro-(4H)-3,1-benzoxazin-4-one derivatives". . p. 29774 - 29781. Retrieved 2015/05/20.