95384-58-0

Basic information

• Product Name: N-(2-hydroxyphenyl)-2-phenylacetamide
• Synonyms: N-(2-hydroxyphenyl)-2-phenylacetamide
• CAS NO: 95384-58-0
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.25852
• Mol File: 95384-58-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2-hydroxyphenyl)-2-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxyphenyl)-2-phenylacetamide(95384-58-0)
• EPA Substance Registry System: N-(2-hydroxyphenyl)-2-phenylacetamide(95384-58-0)

Safety Data

• Hazardous Substances Data: 95384-58-0(Hazardous Substances Data)

Upstream product

• 95-55-6 2-amino-phenol 
• 103-80-0 phenylacetyl chloride 
• 98-80-6 phenylboronic acid 
• 64908-64-1 2-phenoxyisoindol-1,3-dione 
• 4846-21-3 O-phenylhydroxylamine 
• 103-82-2 phenylacetic acid 
• 536-74-3 phenylacetylene 
• 103-83-3 N,N'-dimethylbenzylamine 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 201230-82-2 carbon monoxide 
• 854880-13-0 1-(2-phenyl-acetylamino)-2-valeryloxy-benzene 
• 1001845-90-4 1-benzoyloxy-2-(2-phenyl-acetylamino)-benzene 
• 860744-33-8 1-chloroacetoxy-2-(2-phenyl-acetylamino)-benzene 
• 858446-05-6 1-(2-phenyl-acetylamino)-2-propionyloxy-benzene 

Downstream Products

• 860744-33-8 1-chloroacetoxy-2-(2-phenyl-acetylamino)-benzene 
• 28458-93-7 benzo[d]oxazol-2-yl(phenyl)methanone 
• 132283-16-0 Naphthalene-1-carboxylic acid 2-phenylacetylamino-phenyl ester 
• 692767-36-5 1-acetoxy-2-(2-phenyl-acetylamino)-benzene 

Relevant articles and documents

Visible light-promoted copper catalyzed regioselective acetamidation of terminal alkynes by arylamines

Herein, we describe a copper photoredox catalyzed synthesis of acetamide via regioselective C-N coupling of arylamines with terminal alkynes using molecular oxygen (O2) as an oxidant at room temperature under visible light irradiation (47 examples). Unique simultaneous formation of both amide and ester functionalities occurs via intramolecular cyclization in a single-step reaction in the case of anthranilic acids using inexpensive copper as a catalyst and eco-friendly O2 as an oxidant and reagent. Different substrates undergo different reaction pathways to generate similar acetamide products, as evidenced by 18O2 labelling experiments. The current protocol was also applied for the rapid, few step preparation of biologically active inhibitors (BACE-1 and PDE4). This process can be readily scaled up to a gram scale, and calculations of green metrics suggest the economic feasibility and eco-friendly nature of the current photoredox approach.

Catalytic direct amidations in: Tert -butyl acetate using B(OCH2CF3)3

Catalytic direct amidation reactions have been the focus of considerable recent research effort, due to the widespread use of amide formation processes in pharmaceutical synthesis. However, the vast majority of catalytic amidations are performed in non-polar solvents (aromatic hydrocarbons, ethers) which are typically undesirable from a sustainability perspective, and are often poor at solubilising polar carboxylic acid and amine substrates. As a consequence, most catalytic amidation protocols are unsuccessful when applied to polar and/or functionalised substrates of the kind commonly used in medicinal chemistry. In this paper we report a practical and useful catalytic direct amidation reaction using tert-butyl acetate as the reaction solvent. The use of an ester solvent offers improvements in terms of safety and sustainability, but also leads to an improved reaction scope with regard to polar substrates and less nucleophilic anilines, both of which are important components of amides used in medicinal chemistry. An amidation reaction was scaled up to 100 mmol and proceeded with excellent yield and efficiency, with a measured process mass intensity of 8.

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.

Cp?Rh(III)/Bicyclic Olefin Cocatalyzed C-H Bond Amidation by Intramolecular Amide Transfer

A bicyclic olefin was discovered as a cocatalyst in a Cp?Rh(III)-catalyzed C-H bond amidation proceeding by an intramolecular amide transfer in N-phenoxyacetamide derivatives. Combining experimental and theoretical studies, we propose that the olefin promotes a Rh(III) intermediate to undergo oxidative addition into the O-N bond to form a Rh(V) nitrenoid species and subsequently direct the nitrenoid to add to the ortho position. The amide directing group plays a dual role as a cleavable coordinating moiety as well as an essential coupling partner for the C-H amidation. This methodology was successfully applied to the late-stage diversification of natural products and a marketed drug under mild conditions.

Novel green acylamide synthesis method through quaternary ammonium salt C-N bond fracture

The invention provides a novel green acylamide synthesis method through quaternary ammonium salt C-N bond fracture. The structure of the compound is expressed by methods such as H NMR, C, NMR and HRMS and is confirmed. A series of phenmethyl quaternary ammonium salts and aminated compounds are used; under the catalysis effect of PdCl2(dppf), PPh3 is used as a ligand, Na2CO3 is used as the alkali, and corresponding amide compounds are generated in the 100-DEG C CO atmosphere in a pHMe/DMSO mixed solvent. The method has the advantages that the efficiency is high; the toxicity is low; the conditions are mild; the application range of the substrate is wide; the yield is high; the product purity is high; the separation is convenient; the method can be applicable to large-scale preparation; the application prospects are wide.

Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation

2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.

Nonpeptide inhibitors of measles virus entry

Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-μM blockade of the MV, one of which (AS-48) exhibits IC50 = 0.6-3.0 μM across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.

Smart cleavage reactions: The synthesis of benzimidazoles and benzothiazoles from polymer-bound esters

The preparation of an array of benzimidazoles and benzothiazoles from polymer-bound esters is described. Polymer-bound esters were treated with 2-aminothiophenols or 1,2-phenylenediamines in the presence of a Lewis acid to afford the corresponding benzothiazole or benzimidazole cleavage products. The reaction of 2-aminophenols with the polymer-bound esters failed to give the desired benzoxazole products using this procedure.

Synthesis and microbiological activity of some novel N-(2-hydroxyl-5- substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides as the possible metabolites of antimicrobial active benzoxazoles

Synthesis of some novel N-(2-hydroxyl-5- substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides (5a-k) were described in order to determine their in vitro antimicrobial activity against 3 Gram-positive, 3 Gram-negative bacteria and the fungus Candida albicans comparing with several control drugs. The derivative 5e was found active at a MIC value of 25μg/ml against the whole tested Gram- positive bacteria strains and the Gram-negative microorganism Klebsiella pneumoniae. Moreover, the synthesized compounds 5a-k exhibited significant antibacterial activity against the enterobacter Pseudomonas aureginosae when compared to the control drugs. For the antifungal activity against C. albicans, the compound 5k was found more active than the other synthesized derivatives. On the other hand, the antimicrobial activity of some of these acetamide derivatives (5c, 5d, 5e, 5j and 5k) which are the possible metabolites of benzoxazoles, were also compared with their cyclic analogues 6-10. However, most of the MIC values of the benzoaxazole derivatives provided better activity than the compared acetamides, while some others of the acetamide derivatives possessed either one fold improved (5d, 5e and 5j) or the same potency (5c, 5d, 5e, 5j and 5k) against the tested microorganisms.

Facile synthesis of 2-substituted benzoxazoles via ketenes

The generation of diphenyl-, phenyl-, phenoxy-, and chloroketenes by treatment of the corresponding acid chlorides with triethylamine in the presence of 2-aminophenol resulted in good yields of 2-substituted benzoxazoles.