Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate

Base Information

• Chemical Name: Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate
• CAS No.: 908802-68-6
• Molecular Formula: C12H12N2O3
• Molecular Weight: 232.239
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID40695999
• Wikidata: Q82625399
• Mol file: 908802-68-6.mol

Synonyms:908802-68-6;Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate;3-(4-AMINO-PHENYL)-ISOXAZOLE-5-CARBOXYLIC ACID ETHYL ESTER;ethyl 3-(4-aminophenyl)-1,2-oxazole-5-carboxylate;951626-03-2;3-(4-Amino-phenyl)-isoxazole-5-carboxylicacidethylester;SCHEMBL2294258;DTXSID40695999;UEUPNCATSZRUAV-UHFFFAOYSA-N;SB40193;Ethyl3-(4-aminophenyl)isoxazole-5-carboxylate;A860677;3-(4-amino-phenyl)-isoxazol-5-carboxylic acid ethyl ester

Chemical Property of Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate

Chemical Property:

• PSA: 78.35000
• LogP: 2.68170
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 232.08479225
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

97% ^*data from raw suppliers

Ethyl3-(4-aminophenyl)isoxazole-5-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=NO1)C2=CC=C(C=C2)N

Technology Process of Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate

There total 4 articles about Ethyl 3-(4-aminophenyl)isoxazole-5-carboxylate 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: 82.0%

ethyl 5-(4-nitrophenyl)isoxazole-3-carboxylate (159670-70-9) → ethyl 5-(4-amino-phenyl)isoxazole-3-carboxylate (908802-68-6)

Guidance literature:

With stannous chloride dihydrate; potassium carbonate; In ethyl acetate; for 6h; Reflux;

Reference yield:

5-(4-tert-butoxycarbonylaminophenyl)isoxazole-3-carboxylic acid ethyl ester (908581-03-3) → ethyl 5-(4-amino-phenyl)isoxazole-3-carboxylate (908802-68-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jm8002894

Reference yield:

(4-nitrophenyl)ethanone (100-19-6) → ethyl 5-(4-amino-phenyl)isoxazole-3-carboxylate (908802-68-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium; oxalic acid diethyl ester / 24 h / 20 °C

2: hydroxylamine hydrochloride / ethanol / 4 h / Reflux

3: tin(II) chloride dihdyrate / ethyl acetate / 6 h / Reflux

With tin(II) chloride dihdyrate; hydroxylamine hydrochloride; sodium; oxalic acid diethyl ester; In ethanol; ethyl acetate;

DOI:10.1016/j.bmcl.2014.04.118

upstream raw materials:

5-(4-tert-butoxycarbonylaminophenyl)isoxazole-3-carboxylic acid ethyl ester

4-(4-nitrophenyl)-2,4-dione-butyric acid ethyl ester

ethyl 5-(4-nitrophenyl)isoxazole-3-carboxylate

(4-nitrophenyl)ethanone

Downstream raw materials:

ethyl 4-(5-(4-guanidinophenyl)isoxazole-3-carboxamido)benzoate hydrochloride

5-(4-Guanidinophenyl)-N-p-tolylisoxazole-3-carboxamide hydrochloride

N-(2,6-dimethylphenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride

N-(3-bromophenyl)-5-(4-guanidinophenyl)isoxazole-3-carboxamide hydrochloride

Refernces

• 1、 Zhao, Juntao,Tian, Wei,Qi, Jingjing,Lv, Diya,Liu, Yang,Jiang, Yan,Dong, Guoqiang,Chen, Qianqian,Zhou, Youjun,Zhu, Ju,Wang, Heling,Sheng, Chunquan,Lv, Jiaguo. "Design and synthesis of phenylisoxazole derivatives as novel human acrosin inhibitors". . p. 2802 - 2806. Retrieved 2014/06/10.
• 2、 Kozikowski, Alan P.,Tapadar, Subhasish,Luchini, Doris N.,Ki, Hwan Kim,Billadeau, Daniel D.. "Use of the Nitrile Oxide Cycloaddition (NOC) reaction for molecular probe generation: A new class of enzyme selective histone deacetylase inhibitors (HDACIs) showing picomolar activity at HDAC6". supporting information; experimental part. p. 4370 - 4373. Retrieved 2009/05/30.