4424-17-3

Basic information

• Product Name: 2'-AMINOBENZANILIDE
• Synonyms: 2'-AMINOBENZANILIDE;2-AMINO-N-PHENYL-BENZAMIDE;O-AMINOBENZANILIDE;2-amino-benzanilid;2-amino-n-phenyl-benzamid;anthranilanilide;n-(2-aminobenzoyl)aniline;2-Amino-N-phenylbenzamide~Phenylanthranilamide
• CAS NO: 4424-17-3
• Molecular Formula: C₁₃H₁₂N₂O
• Molecular Weight: 212.25
• EINECS: 224-599-5
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 4424-17-3.mol

Chemical Properties

• Melting Point: 133-134°C
• Boiling Point: 352.09°C (rough estimate)
• Flash Point: 141 °C
• Appearance: /
• Density: 1.1128 (rough estimate)
• Vapor Pressure: 0.00175mmHg at 25°C
• Refractive Index: 1.6920 (estimate)
• PKA: 13.24±0.70(Predicted)
• BRN: 782786
• CAS DataBase Reference: 2'-AMINOBENZANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-AMINOBENZANILIDE(4424-17-3)
• EPA Substance Registry System: 2'-AMINOBENZANILIDE(4424-17-3)

Safety Data

• Safety Statements: 22-24/25
• RTECS: CV2325000
• HazardClass: IRRITANT
• Hazardous Substances Data: 4424-17-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-Aminobenzanilide is used as a key intermediate for the synthesis of various pharmaceuticals. Its presence of amine and amide functional groups allows for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and therapeutic agents.
Used in Dye Industry:
In the dye industry, 2'-Aminobenzanilide serves as an intermediate for the production of different types of dyes. Its chemical structure facilitates the creation of dyes with specific color properties, enhancing the range of colorants available for various applications.
Used in Industrial Processes:
2'-Aminobenzanilide is studied for its potential use as a corrosion inhibitor. Its application in this field aims to protect materials from corrosion, extending their lifespan and improving the efficiency of industrial processes by reducing maintenance and replacement costs.

InChI:InChI=1/C13H12N2O/c14-11-8-4-5-9-12(11)15-13(16)10-6-2-1-3-7-10/h1-9H,14H2,(H,15,16)

Upstream product

• 118-48-9 isatoic anhydride 
• 864131-95-3 N,N'-diphenylformamidine 
• 62-53-3 aniline 
• 2385-27-5 N-phenyl-2-nitrobenzamide 
• 7647-01-0 hydrogenchloride 
• 861326-09-2 sulfurous acid mono-(1-oxy-2-phenyl-2H-indazol-3-yl ester) 
• 67-56-1 methanol 
• 91-56-5 indole-2,3-dione 
• 552-16-9 ortho-nitrobenzoic acid 
• 2099-63-0 anthranilic acid hydrochloride 
• 123767-94-2 anthraniloyl chloride ; hydrochloride 
• 108-86-1 bromobenzene 
• 28144-70-9 anthranilic acid amide 
• 7664-93-9 sulfuric acid 

Downstream Products

• 13220-57-0 tryptanthrine 
• 54364-31-7 2-(Acetylamino)-N-phenylbenzamide 
• 16347-60-7 3-phenyl-4(3H)-quinazolinone 
• 94565-37-4 2-(3,4-dimethoxyphenyl)-3-phenyl-1,2,3,4-tetrahydroquinazolin-4-one 
• 143424-18-4 2-{[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-amino}-N-phenyl-benzamide 
• 143424-13-9 2-(2,4-dimethoxy-benzylideneamino)-N-phenyl-benzamide 
• 34237-88-2 N-phenyl-2-(phenylamino)benzamide 
• 22686-82-4 2,3-diphenyl-3H-quinazolin-4-one 
• 5605-26-5 2-propyl-3-phenyl-3H-quinazolin-4-one 
• 306324-91-4 2-(2-hydroxy-benzylideneamino)-N-phenyl-benzamide 
• 139602-69-0 2-(3,4-Dimethoxy-benzylamino)-N-phenyl-benzamide 
• 139602-64-5 2-(2,4-Dimethoxy-benzylamino)-N-phenyl-benzamide 
• 143424-28-6 2-[Acetyl-(3,4-dimethoxy-benzyl)-amino]-N-phenyl-benzamide 
• 143424-23-1 2-[Acetyl-(2,4-dimethoxy-benzyl)-amino]-N-phenyl-benzamide 

Relevant articles and documents

UV-Light-Induced Dehydrogenative N -Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.

Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl) benzamides/sulphonamides: The stereoselective synthesis of 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[f][1,2,5]thiadiazepine-1,1-dioxides

The Pd(0) catalysed cyclisation reactions betweentert-butyl propargyl carbonates and 2-aminotosyl benzamides or sulphonamides deliver 1,4-benzodiazepin-5-ones or sultam derivatives, key components of many biologically active compounds. But 2-amino benzamides/sulphonamides require propargyl carbonates substituted at acetylenic carbon to undergo the reaction resulting in the stereoselective formation of the said products.

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.

Efficient synthesis of 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives catalyzed by functionalized nanoporous silica

An efficient and facile method has been developed for the synthesis of various 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives, via a three-component reaction of 2-amino-N-(R)-benzamide derivatives with 2-formylbenzoic acid using sulfonic acid functionalized nanoporous silica as an efficient catalyst in ethanol under reflux. High yield of the desired products, reusability of the catalyst, and effortless workup step without using chromatography are the advantages of this method. Graphic abstract: [Figure not available: see fulltext.]

Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives

A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.

Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one

Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.

N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones

N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.

Microwave-promoted one-pot three-component synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by heteropolyanion-based ionic liquids under solvent-free conditions

A series of 2,3-dihydroquinazoline-4(1H)-one derivatives have been synthesized via one-pot three-component reaction using isatoic anhydrides, amines and aldehydes (or ketones) catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions. The practical protocol was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, solvent-free media and operational simplicity are the main highlights. Furthermore, the catalyst can be recovered and reused without evident loss of reactivity. This method provides a green and much improved protocol over the existing methods.

Regioselective Br?nsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with N′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2- a]quinazolin-5(1 H)ones

A highly regioselective synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N′-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form desired tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one in good to excellent yield with complete regioselectivity. This protocol tolerates a great variety of functional groups and thus provides a simple and step-efficient method for pyrroloquinazolinone synthesis.