4943-85-5

Basic information

• Product Name: 2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE
• Synonyms: 2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE;BENZAMIDE, 2-AMINO-N-(2-METHYLPHENYL)-;OTAVA-BB 1133397;2-Amino-benzoesaeure-o-toluidid
• CAS NO: 4943-85-5
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.27
• Mol File: 4943-85-5.mol
• Article Data: 20

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE(4943-85-5)
• EPA Substance Registry System: 2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE(4943-85-5)

Safety Data

• Hazardous Substances Data: 4943-85-5(Hazardous Substances Data)

Usage

General Description

2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE is an organic chemical compound with the molecular formula C14H13N3O. It is a benzamide derivative containing an amine group and a methylphenyl group. 2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE is commonly used in the pharmaceutical industry for the synthesis of various drugs and pharmaceuticals. It has been studied for its potential therapeutic properties, including anti-inflammatory and anti-cancer activities. Additionally, 2-AMINO-N-(2-METHYLPHENYL)BENZAMIDE is used as a building block in organic synthesis and as a reagent in chemical reactions.

Synthetic route

2-nitro-N-(2-tolyl)benzamide (2385-25-3) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 50℃; for 24h;	99%
With tetrahydroxydiboron; palladium on activated charcoal; water In acetonitrile at 50℃; for 24h; Inert atmosphere;	99%
With hydrogen; palladium on activated charcoal In ethyl acetate under 750.075 Torr;	87%

2-methylchlorobenzene (95-49-8) + anthranilic acid amide (28144-70-9) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + 2-(2-methylphenylamino)benzamide (95216-60-7)

Conditions	Yield
With palladium diacetate; potassium carbonate; XPhos In tert-butyl alcohol at 110℃; for 17h;	A 10% B 87%

isatoic anhydride (118-48-9) + o-toluidine (95-53-4) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
With aqueous extract of mesocarp of fruit of Balanites roxburghii plant at 60℃; for 0.333333h;	83%
In ethanol for 20h; Reflux;	67%

o-toluidine (95-53-4) + 2-aminobenzoyl chloride (21563-73-5) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
In diethyl ether at 0 - 10℃; for 0.5h;	81.39%

isatoic anhydride (118-48-9) + o-Methylbenzamid (527-85-5) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
In ethyl acetate at 90℃; for 18h;	50%

methaqualone (72-44-6) → 2-Acetamidobenzoesaeure-2'-methylanilid (70180-39-1) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + o-toluidine (95-53-4)

Conditions	Yield
With sodium hydroxide for 7h; Heating; hydrolysis;

o-toluidine (95-53-4) + chloric acid → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / aq. K2CO3 / tetrahydrofuran / 12 h / Heating 2: 51 percent / H2 / 5percent Pd/C / 3 h / 2327.2 Torr View Scheme

2-nitrobenzyl chloride (610-14-0) + 3-<β-amino-ethyl>-indole-carboxylic acid-(2) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / aq. K2CO3 / tetrahydrofuran / 12 h / Heating 2: 51 percent / H2 / 5percent Pd/C / 3 h / 2327.2 Torr View Scheme

6'-triisopropylbiphenyl + 2-methylchlorobenzene (95-49-8) + anthranilic acid amide (28144-70-9) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + 2-(2-methylphenylamino)benzamide (95216-60-7)

Conditions	Yield
With potassium carbonate; tris-(dibenzylideneacetone)dipalladium(0) In hexane	A 98 mg (87%) B n/a

anthranilic acid (118-92-3) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 4.5 h / 80 °C 2: diethyl ether / 0.5 h / 0 - 10 °C View Scheme

ortho-nitrobenzoic acid (552-16-9) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C 2: triethylamine / dichloromethane 3: ammonium chloride; zinc / tetrahydrofuran; water / 20 °C View Scheme

2-nitrobenzyl chloride (610-14-0) → 2-amino-N-(2-methylphenyl)benzamide (4943-85-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: ammonium chloride; zinc / tetrahydrofuran; water / 20 °C View Scheme

1,3-cylohexanedione (504-02-9) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → 2-(4-oxopentyl)-3-(o-tolyl)quinazolin-4-one

Conditions	Yield
With camphor-10-sulfonic acid In water; ethyl acetate at 100℃; for 24h;	99%
With camphor-10-sulfonic acid In water at 100℃; for 24h; Green chemistry;	69%

ethanol (64-17-5) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → methaqualone (72-44-6)

Conditions	Yield
Stage #1: ethanol With oxygen; eosin y In dimethyl sulfoxide at 25℃; for 20h; Sealed tube; Irradiation; Green chemistry; Stage #2: 2-amino-N-(2-methylphenyl)benzamide With toluene-4-sulfonic acid In dimethyl sulfoxide at 25℃; for 24h; Reagent/catalyst; Wavelength; Temperature; Solvent; Sealed tube; Irradiation; Green chemistry;	98%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] at 150℃; for 24h; Inert atmosphere; Sealed tube;	97%

thiophene-2-carbaldehyde (98-03-3) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → 2-Thiophen-2-yl-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one

Conditions	Yield
With acetic acid In ethanol Heating;	95%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + acetylacetone (123-54-6) → methaqualone (72-44-6)

Conditions	Yield
With camphor-10-sulfonic acid In water at 100℃; for 16h; Green chemistry;	93%
With camphor-10-sulfonic acid In water at 100℃; for 24h;	93%
With toluene-4-sulfonic acid In toluene at 120℃; for 10h; Sealed tube;	89%
With iron(III) chloride hexahydrate In water at 100℃; for 24h; Green chemistry;	73%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + Glyoxilic acid (298-12-4) → 3-(2-methylphenyl)quinazolin-4(3H)-one (16899-50-6)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; di-tert-butyl peroxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 120℃; for 24h; Schlenk technique;	92%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + isobutyraldehyde (78-84-2) → 2-Isopropyl-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one

Conditions	Yield
With acetic acid In ethanol Heating;	91%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → 3-(2-methylphenyl)benzo-1,2,3-triazin-4(3H)-one (54970-85-3)

Conditions	Yield
With tert.-butylnitrite; saccharin In ethanol at 50℃; for 6h; Green chemistry;	90%
With tert.-butylnitrite; tetra-(n-butyl)ammonium iodide In acetonitrile at 60℃; for 12h; Green chemistry;	85%
With toluene-4-sulfonic acid In methanol at 0 - 40℃; for 5h;	77%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + acetaldehyde (75-07-0) → 2-methyl-3-(o-tolyl)-2,3-dihydro-4(1H)-quinazolinone (1773-01-9)

Conditions	Yield
With acetic acid In ethanol Heating;	88%
With L-Tartaric acid; N,N'-Dimethylurea at 90℃; Green chemistry;	87%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + acetone (67-64-1) → 2,2-Dimethyl-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one

Conditions	Yield
With acetic acid In ethanol Heating;	85%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + butanone (78-93-3) → 2-methyl-2-ethyl-3-(o-tolyl)-2,3-dihydro-4(1H)-quinazolinone (66074-09-7)

Conditions	Yield
With acetic acid In ethanol Heating;	85%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + propionaldehyde (123-38-6) → 2-Ethyl-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one

Conditions	Yield
With acetic acid In ethanol Heating;	81%

formaldehyd (50-00-0) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → 3-(o-tolyl)-2,3-dihydro-4(1H)-quinazolinone (1086-23-3)

Conditions	Yield
With acetic acid In ethanol Heating;	75%

bis(1-methyl-1-phenylethyl)peroxide (80-43-3) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → 3-(2-methylphenyl)quinazolin-4(3H)-one (16899-50-6)

Conditions	Yield
With 1H-imidazole; copper(II) acetate monohydrate In chlorobenzene at 120℃; for 10h;	75%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + benzaldehyde (100-52-7) → 2-phenyl-3-(o-tolyl)-2,3-dihydro-4(1H)-quinazolinone (16285-34-0)

Conditions	Yield
With acetic acid In ethanol Heating;	72%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + PEG-400 → methaqualone (72-44-6)

Conditions	Yield
With p-toluenesulfonic acid monohydrate; oxygen at 110℃; Sealed tube; Green chemistry;	71%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → 3-(2-methylphenyl)quinazolin-4(3H)-one (16899-50-6)

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile at 70℃; for 24h;	70%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + vanillin (121-33-5) → 2-(4-Hydroxy-3-methoxy-phenyl)-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one (94565-58-9)

Conditions	Yield
In ethanol water bath;	67%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + Benzoylformic acid (611-73-4) → 3-(2-methylphenyl)-2-phenylquinazolin-4(3H)-one (37856-16-9)

Conditions	Yield
With tetraethylammonium hexafluorophosphate In 2,2,2-trifluoroethanol at 20℃; for 6h; Electrochemical reaction; Green chemistry;	66%

LACTIC ACID (849585-22-4) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → methaqualone (72-44-6)

Conditions	Yield
With tert.-butylhydroperoxide In water; 1,2-dichloro-ethane at 80℃; for 36h;	63%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + dimethyl sulfoxide (67-68-5) → 3-(2-methylphenyl)quinazolin-4(3H)-one (16899-50-6)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; dipotassium peroxodisulfate at 160℃; for 2h; Microwave irradiation;	61%

(E)-3-phenylpropenal (14371-10-9) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → 2-((E)-Styryl)-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one (94565-43-2)

Conditions	Yield
In ethanol water bath;	60%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + sodium chlorodifluoroacetate (1895-39-2) → 3-(2-methylphenyl)quinazolin-4(3H)-one (16899-50-6)

Conditions	Yield
With caesium carbonate In acetonitrile at 120℃; for 24h; Schlenk technique;	60%

diethyl sulphide (70-29-1) + 2-amino-N-(2-methylphenyl)benzamide (4943-85-5) → methaqualone (72-44-6)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; dipotassium peroxodisulfate In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 2h; Microwave irradiation;	57%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + pivalaldehyde (630-19-3) → 2-tert-Butyl-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one

Conditions	Yield
With acetic acid In ethanol Heating;	54%

2-amino-N-(2-methylphenyl)benzamide (4943-85-5) + salicylaldehyde (90-02-8) → 2-(2-Hydroxy-phenyl)-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one (94565-46-5)

Conditions	Yield
In ethanol water bath;	50%

Upstream product

• 118-48-9 isatoic anhydride 
• 95-53-4 o-toluidine 
• 72-44-6 methaqualone 
• 2385-25-3 2-nitro-N-(2-tolyl)benzamide 
• 95-49-8 2-methylchlorobenzene 
• 28144-70-9 anthranilic acid amide 
• 610-14-0 2-nitrobenzyl chloride 
• 118-92-3 anthranilic acid 
• 21563-73-5 2-aminobenzoyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 527-85-5 o-Methylbenzamid 

Downstream Products

• 54970-85-3 3-(2-methylphenyl)benzo-1,2,3-triazin-4(3H)-one 
• 28439-81-8 (2-o-tolylcarbamoyl-phenyl)-oxalamic acid ethyl ester 
• 32203-03-5 2-phenyl-3-o-tolyl-2,3-dihydro-1H-benzo[1,3,2]diazaborinin-4-one 
• 94565-43-2 2-((E)-Styryl)-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one 
• 16899-50-6 3-(2-methylphenyl)quinazolin-4(3H)-one 
• 94565-55-6 2-(4-Hydroxy-phenyl)-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one 
• 94565-58-9 2-(4-Hydroxy-3-methoxy-phenyl)-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one 
• 94565-38-5 2-(3,4-Dimethoxy-phenyl)-3-o-tolyl-2,3-dihydro-1H-quinazolin-4-one 
• 1086-23-3 3-(o-tolyl)-2,3-dihydro-4(1H)-quinazolinone 
• 1773-01-9 2-methyl-3-(o-tolyl)-2,3-dihydro-4(1H)-quinazolinone 
• 66074-09-7 2-methyl-2-ethyl-3-(o-tolyl)-2,3-dihydro-4(1H)-quinazolinone 
• 127662-25-3 3-o-tolyl-1,2,3,4-tetrahydro-quinazoline 
• 28439-80-7 N-(3-morpholin-4-yl-propyl)-N'-(2-o-tolylcarbamoyl-phenyl)-oxalamide 
• 28439-83-0 N-(2-Dimethylamino-ethyl)-N'-(2-o-tolylcarbamoyl-phenyl)-oxalamide 

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