N-(2-nitrophenyl)-2-phenylacetamide

Base Information

• Chemical Name: N-(2-nitrophenyl)-2-phenylacetamide
• CAS No.: 1504-26-3
• Molecular Formula: C14H12N2O3
• Molecular Weight: 256.261
• DSSTox Substance ID: DTXSID10877422
• Nikkaji Number: J1.604.276E
• Wikidata: Q82859220
• ChEMBL ID: CHEMBL386964
• Mol file: 1504-26-3.mol

Synonyms:1504-26-3;N-(2-nitrophenyl)-2-phenylacetamide;o-Nitrobenzylformanilid;Oprea1_410729;CHEMBL386964;SCHEMBL3260677;DTXSID10877422;N-(2-Nitrophenyl)benzeneacetamide;STK299878;AKOS000604348;Benzeneacetamide, N-(2-nitrophenyl)-;SR-01000200722;SR-01000200722-1

Chemical Property of N-(2-nitrophenyl)-2-phenylacetamide

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 256.08479225
• Heavy Atom Count: 19
• Complexity: 321

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(=O)NC2=CC=CC=C2[N+](=O)[O-]

Technology Process of N-(2-nitrophenyl)-2-phenylacetamide

There total 9 articles about N-(2-nitrophenyl)-2-phenylacetamide 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: 81.0%

phenylacetic acid (103-82-2) + 2-nitro-aniline (88-74-4) → N-(2-nitrophenyl)-2-phenylacetamide (1504-26-3)

Guidance literature:

phenylacetic acid; With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at -15 - 20 ℃; for 2h; Inert atmosphere;

2-nitro-aniline; With potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.1c00406

Reference yield: 70.0%

2-nitro-aniline (88-74-4) + benzeneacetic acid methyl ester (101-41-7) → N-(2-nitrophenyl)-2-phenylacetamide (1504-26-3)

Guidance literature:

With zinc; In N,N-dimethyl-formamide; for 0.133333h; microwave irradiation;

DOI:10.1139/v05-134

Reference yield: 60.0%

2-nitrophenyl bromide (577-19-5) + potassium (2-phenyl-1-((trimethylsilyl)oxy)ethylidene)amide → N-(2-nitrophenyl)-2-phenylacetamide (1504-26-3)

Guidance literature:

potassium (2-phenyl-1-((trimethylsilyl)oxy)ethylidene)amide; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos; In 1,4-dioxane; at 100 ℃; for 0.166667h;

2-nitrophenyl bromide; In 1,4-dioxane; at 100 ℃; for 16h;

DOI:10.1055/s-0035-1560724

upstream raw materials:

phenylacetic acid

2-nitro-aniline

benzeneacetic acid methyl ester

phenylacetyl chloride

Downstream raw materials:

2-benzylbenzimidazole

Refernces

• 1、 McPherson, Christopher G.,Livingstone, Keith,Jamieson, Craig,Simpson, Iain. "Palladium-Catalyzed Synthesis of Aryl Amides through Silanoate-Mediated Hydrolysis of Nitriles". supporting information. p. 88 - 92. Retrieved 2015/12/26.
• 2、 Duchek, Jan,Vasella, Andrea. "Synthesis of benzimidazoles by phosphine-mediated reductive cyclisation of ortho-nitro-anilides". experimental part. p. 977 - 986. Retrieved 2011/08/05.