3-(4-Methoxyanilino)crotonic acid ethyl ester

Base Information

• Chemical Name: 3-(4-Methoxyanilino)crotonic acid ethyl ester
• CAS No.: 33240-23-2
• Molecular Formula: C13H17 N O3
• Molecular Weight: 235.283
• NSC Number: 25203
• Nikkaji Number: J2.249.336A,J605.032H
• Mol file: 33240-23-2.mol

Synonyms:NSC25203;SCHEMBL10558287;HMS1398A04;NSC-25203;AKOS015831617;3-(4-Methoxyanilino)crotonic acid ethyl ester;ethyl (z)-3-(4-methoxyanilino)-2-butenoate;3-(4-Methoxyphenylamino)-2-butenoic acid ethyl ester;33240-23-2

Chemical Property of 3-(4-Methoxyanilino)crotonic acid ethyl ester

Chemical Property:

• Vapor Pressure: 5.06E-05mmHg at 25°C
• Boiling Point: 348.3°C at 760 mmHg
• Flash Point: 164.5°C
• Density: 1.108g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 235.12084340
• Heavy Atom Count: 17
• Complexity: 268

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=C(C)NC1=CC=C(C=C1)OC
• Isomeric SMILES: CCOC(=O)/C=C(/C)\NC1=CC=C(C=C1)OC

Technology Process of 3-(4-Methoxyanilino)crotonic acid ethyl ester

There total 5 articles about 3-(4-Methoxyanilino)crotonic acid ethyl ester 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: 98.0%

ethyl acetoacetate (141-97-9) + 4-methoxy-aniline (104-94-9) → ethyl (Z)-3-(4-methoxyanilino)-2-butenoate (33240-23-2,66558-24-5)

Guidance literature:

With iron(III) trifluoromethanesulfonate; In neat (no solvent); at 20 ℃; for 0.0666667h; Green chemistry;

DOI:10.2478/s11696-014-0544-8

Reference yield: 97.0%

ethyl acetoacetate (141-97-9) + 4-methoxy-aniline (104-94-9) → ethyl 3-((4-methoxyphenyl)amino)but-2-enoate (33240-23-2)

Guidance literature:

With [Cu(naphthalene-2,6-disulfonate)_0.5(2,4,5-tri(4-pyridyl)imidazole)]_n; In neat (no solvent); at 20 ℃; for 0.5h; chemoselective reaction;

DOI:10.1016/j.ica.2015.03.014

Reference yield: 80.0%

4-methoxy-aniline (104-94-9) + acetoacetic acid methyl ester (105-45-3) → ethyl (Z)-3-(4-methoxyanilino)-2-butenoate (33240-23-2,66558-24-5)

Guidance literature:

With iron ethylene-1,2-diamine complex loaded on carbon nanotubes; In 1,2-dichloro-ethane; at 80 ℃; for 24h; under 750.075 Torr;

DOI:10.1002/chem.201905468

upstream raw materials:

ethyl acetoacetate

4-methoxy-aniline

Ethyl 2-butynoate

acetoacetic acid methyl ester

Downstream raw materials:

6-methoxy-2-methylquinolin-4-ol

5-[1-(4-methoxy-anilino)-ethylidene]-3-methyl-[1,3]oxazinane-2,4,6-trione

ethyl acetoacetate

4-methoxy-aniline

Refernces

• 1、 Wu, Lisha,Yan, Shiqiang,Wang, Wensheng,Li, Yinta. "Multicomponent reaction for the synthesis of highly functionalized piperidine scaffolds catalyzed by TMSI". . p. 4311 - 4322. Retrieved 2020/07/13.
• 2、 Baell, Jonathan B.,Ding, Qifeng,Huang, Fei,Huang, He,Xu, Mingjie,Yu, Yang,Zhang, Lihui,Zheng, Jian-Guo. "A Reusable CNT-Supported Single-Atom Iron Catalyst for the Highly Efficient Synthesis of C?N Bonds". supporting information. . Retrieved 2020/03/24.