5260-41-3

Basic information

• Product Name: 4(3H)-Quinazolinone, 2-ethyl-3-phenyl-
• CAS NO: 5260-41-3
• Molecular Formula: C16H14N2O
• Molecular Weight: 250.3
• Mol File: 5260-41-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 4(3H)-Quinazolinone, 2-ethyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(3H)-Quinazolinone, 2-ethyl-3-phenyl-(5260-41-3)
• EPA Substance Registry System: 4(3H)-Quinazolinone, 2-ethyl-3-phenyl-(5260-41-3)

Safety Data

• Hazardous Substances Data: 5260-41-3(Hazardous Substances Data)

Usage

General Description

4(3H)-Quinazolinone, 2-ethyl-3-phenyl- is a chemical compound with the molecular formula C17H14N2O. It is a quinazolinone derivative, a class of compounds with potential biological and pharmaceutical applications. This specific compound is used in the synthesis and development of pharmaceutical drugs, particularly for its potential as an antitumor and anticancer agent. It has also been studied for its potential antifungal and antibacterial properties. Additionally, 4(3H)-Quinazolinone, 2-ethyl-3-phenyl- has shown promise in the development of new treatments for neurological disorders and inflammatory diseases.

Synthetic route

2-aminobenzanilide (4424-17-3) + Triethyl orthopropionate (115-80-0) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
With acetic acid In ethanol at 110℃; for 24h; Inert atmosphere; Sealed tube;	92%

ethylmagnesium bromide (925-90-6) + 1-phenyl-3-(2-ethoxycarbonylphenyl) carbodiimide (622403-42-3) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 3h;	69%

3-(2,6-dibromophenyl)-2-ethylquinazolin-4(3H)-one → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) + (P)-3-(2-bromophenyl)-2-ethylquinazolin-4(3H)-one + 3-(2-bromophenyl)-2-ethylquinazolin-4(3H)-one

Conditions	Yield
With sodium tetrahydroborate; (R)-DTBM-SEGPHOS; palladium diacetate In N,N-dimethyl-formamide at 0℃; for 21h; Inert atmosphere; enantioselective reaction;	A 45% B 35% C n/a

2-ethyl-benzo[d][1,3]oxazin-4-one (2916-09-8) + aniline (62-53-3) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
With trichlorophosphate In dichloromethane for 4h; Heating;	42%

N-propionyl-anthranilic acid anilide (25628-85-7) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
at 250℃;

N-(2-benzoylphenyl)propionamide (549500-24-5) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
With sodium azide; chloroform; sulfuric acid

aniline (62-53-3) + 2-(propionylamino)benzoic acid (19165-26-5) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
With phosphorus trichloride
With phosphorus trichloride In toluene
With phosphorus trichloride In toluene at 110℃;

anthranilic acid (118-92-3) + 1-chloro-4-methyl-thioxanthone → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / 4 h / Heating 2: 42 percent / phosphorus oxychloride / CH2Cl2 / 4 h / Heating View Scheme

anthranilic acid (118-92-3) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / dimethylformamide 2: PCl3 / toluene View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 2 h / 0 °C 2: phosphorus trichloride / toluene / 110 °C View Scheme

C16H18N2 → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium iodide / ethanol; water / 6 h / 20 °C 2: piperidine / 20 - 50 °C View Scheme

C20H24N2O2 → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
With piperidine at 20 - 50℃; Kornblum decomposition;

N-(2-nitrobenzyl)aniline (33331-19-0) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: platinum(IV) oxide; hydrogen / ethanol / 20 °C 2: ethanol / 5 h / 20 °C 3: potassium iodide / ethanol; water / 6 h / 20 °C 4: piperidine / 20 - 50 °C View Scheme

N-(2-aminobenzyl)aniline (20887-06-3) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 5 h / 20 °C 2: potassium iodide / ethanol; water / 6 h / 20 °C 3: piperidine / 20 - 50 °C View Scheme

aniline (62-53-3) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: benzene / 5 h / Reflux; Dean Stark apparatus 1.2: 20 °C 2.1: platinum(IV) oxide; hydrogen / ethanol / 20 °C 3.1: ethanol / 5 h / 20 °C 4.1: potassium iodide / ethanol; water / 6 h / 20 °C 5.1: piperidine / 20 - 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / benzene / 2 h / Inert atmosphere; Reflux 1.2: 4 h / 0 - 20 °C / Inert atmosphere 1.3: 2 h / 85 °C / Inert atmosphere 2.1: acetic acid / ethanol / 24 h / 110 °C / Inert atmosphere; Sealed tube View Scheme

2-nitro-benzaldehyde (552-89-6) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: benzene / 5 h / Reflux; Dean Stark apparatus 1.2: 20 °C 2.1: platinum(IV) oxide; hydrogen / ethanol / 20 °C 3.1: ethanol / 5 h / 20 °C 4.1: potassium iodide / ethanol; water / 6 h / 20 °C 5.1: piperidine / 20 - 50 °C View Scheme

ethyl 2-(triphenylphosphoranylidene-amino)benzoate (179039-70-4) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 5 h / 0 - 20 °C 2: tetrahydrofuran / 3 h / -78 - 20 °C View Scheme

2-azidobenzoic acid ethyl ester (90408-05-2) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: dichloromethane / 5 h / 0 - 20 °C 3: tetrahydrofuran / 3 h / -78 - 20 °C View Scheme

2-aminobenzanilide (4424-17-3) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(I) oxide; tricyclohexylphosphine / chloroform / 24 h / 100 °C / Schlenk technique; Sealed tube 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 1 h / 20 °C / Schlenk technique; Sealed tube View Scheme

2-ethyl-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (38511-63-6) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform at 20℃; for 1h; Schlenk technique; Sealed tube;	40.5 mg

2,6-dibromoaniline (608-30-0) + 2-(propionylamino)benzoic acid (19165-26-5) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) + (P)-3-(2-bromophenyl)-2-ethylquinazolin-4(3H)-one + 3-(2-bromophenyl)-2-ethylquinazolin-4(3H)-one

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus trichloride / toluene / 20 h / 80 - 120 °C / Inert atmosphere 2: palladium diacetate; sodium tetrahydroborate; (R)-DTBM-SEGPHOS / N,N-dimethyl-formamide / 21 h / 0 °C / Inert atmosphere View Scheme

ortho-nitrobenzoic acid (552-16-9) → 2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride / benzene / 2 h / Inert atmosphere; Reflux 1.2: 4 h / 0 - 20 °C / Inert atmosphere 1.3: 2 h / 85 °C / Inert atmosphere 2.1: acetic acid / ethanol / 24 h / 110 °C / Inert atmosphere; Sealed tube View Scheme

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) → 2-(1-bromoethyl)-3-phenylquinazolin-4(3H)-one (860002-83-1)

Conditions	Yield
With bromine; sodium acetate; acetic acid at 20℃; for 3h;	55%
With bromine; sodium acetate; acetic acid

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) + phenylmagnesium bromide → 2-ethyl-4,4-diphenyl-4H-benzo[d][1,3]oxazine (50547-57-4)

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) → 2-[1-(2-dimethylamino-ethylamino)-ethyl]-3-phenyl-3H-quinazolin-4-one (860002-89-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2; AcOH; AcONa 2: ethanol / Heating View Scheme

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) → decanoic acid (2-dimethylamino-ethyl)-[1-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl)-ethyl]-amide

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2; AcOH; AcONa 2: ethanol / Heating 3: Et3N / dioxane View Scheme

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) → 2-(1-(4-amino-3-(3-fluoro-4-isopropoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-phenylquinazolin-4(3H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / 3 h / 20 °C 2: N,N-dimethyl-formamide / 12 h / 20 °C 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 14 h / 100 °C View Scheme

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) → C30H24FN7O2

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / 3 h / 20 °C 2: N,N-dimethyl-formamide / 12 h / 20 °C 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 14 h / 100 °C View Scheme

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) → 2-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-phenylquinazolin-4(3H)-one

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; acetic acid; bromine / 3 h / 20 °C 2: N,N-dimethyl-formamide / 12 h / 20 °C View Scheme

2-ethyl-3-phenyl-3H-quinazolin-4-one (5260-41-3) → 2-(1-(4-amino-3-(2,3-difluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-3-phenylquinazolin-4(3H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium acetate; acetic acid; bromine / 3 h / 20 °C 2: N,N-dimethyl-formamide / 12 h / 20 °C 3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 14 h / 100 °C View Scheme

Upstream product

• 552-16-9 ortho-nitrobenzoic acid 
• 4424-17-3 2-aminobenzanilide 
• 115-80-0 Triethyl orthopropionate 
• 608-30-0 2,6-dibromoaniline 
• 19165-26-5 2-(propionylamino)benzoic acid 
• 38511-63-6 2-ethyl-3-phenyl-2,3-dihydroquinazolin-4(1H)-one 
• 90408-05-2 o-azidobenzoic acid ethyl ester 
• 179039-70-4 ethyl 2-(triphenylphosphoranylidene-amino)benzoate 
• 925-90-6 ethylmagnesium bromide 
• 622403-42-3 1-phenyl-3-(2-ethoxycarbonylphenyl) carbodiimide 
• 552-89-6 2-nitro-benzaldehyde 
• 62-53-3 aniline 
• 20887-06-3 N-(2-aminobenzyl)aniline 
• 33331-19-0 N-(2-nitrobenzyl)aniline 

Downstream Products

• 860002-83-1 2-(1-bromoethyl)-3-phenylquinazolin-4(3H)-one 
• 132982-00-4 3-phenyl-2-ethylquinazoline-4(3H)-thione 
• 860002-89-7 2-[1-(2-dimethylamino-ethylamino)-ethyl]-3-phenyl-3H-quinazolin-4-one 
• 50547-57-4 2-ethyl-4,4-diphenyl-4H-benzo[d][1,3]oxazine 

Relevant articles and documents

Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination

Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N-C axial chirality) and a chiral carbon.

Quinazolin-4(3H)-ones and 5,6-dihydropyrimidin-4(3H)-ones from β-aminoamides and orthoesters

Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12–24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110?C for 12–72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, 1H-NMR, 13C-NMR, and HRMS.

Catalytic Enantioselective Synthesis of N-C Axially Chiral Mebroqualone and Its Derivatives through Reductive Asymmetric Desymmetrization

In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2 catalyst, treatment of various 3-(2,6-dibromophenyl)quinazolin-4-ones with NaBH4 gave optically active N-C axially chiral quinazolinone (mebroqualone) derivatives through reductive asymmet