30507-16-5

Basic information

• Product Name: 3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one
• Synonyms: 3-(4-Methoxy-phenyl)-2-methyl-3H-quinazolin-4-one; 4(3H)-quinazolinone, 3-(4-methoxyphenyl)-2-methyl-
• CAS NO: 30507-16-5
• Molecular Formula: C₁₆H₁₄N₂O₂
• Molecular Weight: 266.2946
• Mol File: 30507-16-5.mol

Chemical Properties

• Boiling Point: 448.5°C at 760 mmHg
• Flash Point: 225°C
• Density: 1.19g/cm³
• Vapor Pressure: 3.1E-08mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: 3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one(30507-16-5)
• EPA Substance Registry System: 3-(4-methoxyphenyl)-2-methylquinazolin-4(3H)-one(30507-16-5)

Safety Data

• Hazardous Substances Data: 30507-16-5(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 89-52-1 o-acetylamino-benzoic acid 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 36684-49-8 2-iodo-N-(4-methoxyphenyl)benzamide 
• 143-37-3 acetamidine 
• 118-48-9 isatoic anhydride 
• 78-39-7 Triethyl orthoacetate 
• 64-19-7 acetic acid 
• 25116-00-1 2-acetamidobenzonitrile 
• 123-54-6 acetylacetone 
• 20878-54-0 2-amino-N-(4-methoxyphenyl)benzamide 
• 95970-05-1 2,6-dibromo-4-methoxyaniline 
• 100-17-4 para-methoxynitrobenzene 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 1789-09-9 1-(2-methyl-4-oxo-4H-quinazolin-3-yl)-4-hydroxybenzene 
• 80884-25-9 2-Bromomethyl-3-(4-methoxy-phenyl)-3H-quinazolin-4-one 
• 80884-15-7 3-(4-Methoxy-phenyl)-2-[(2-p-tolyl-ethylamino)-methyl]-3H-quinazolin-4-one 
• 80884-17-9 2-{[2-(4-Chloro-phenyl)-ethylamino]-methyl}-3-(4-methoxy-phenyl)-3H-quinazolin-4-one 
• 80884-20-4 2-[(2,4-Dichloro-benzylamino)-methyl]-3-(4-methoxy-phenyl)-3H-quinazolin-4-one 
• 115781-70-9 3-(p-methoxyphenyl)-2-styryl-3,4-dihydro-4-quinazolone 
• 30507-26-7 (E)-3-(4-methoxyphenyl)-2-(4-methoxystyryl)quinazolin-4(3H)-one 

Relevant articles and documents

Metal-free C-H methylation and acetylation of heteroarenes with PEG-400

The generation of a methyl carbon source from renewable and cheap sources is challenging. Herein, we describe a novel and an efficient route for methylation and acetylation of aza-heteroarenes using PEG-400 under O2and TsOH·H2O for the first time by tuning the reaction conditions using a different set of starting materials. The key features of the current protocol are oxidative C-O and C-C bond scission under metal-free conditions with good functional group tolerance, and a broad substrate scope. The potential applicability of the designed methodology was demonstrated for the synthesis of central nervous system (CNS) depressant and anticonvulsant drug molecules by a one-pot strategy.

Screening of natural deep eutectic solvents for green synthesis of 2-methyl-3-substituted quinazolinones and microwave-assisted synthesis of 3-aryl quinazolinones in ethanol

In this study, two fast and efficient protocols for green synthesis of 3-substituted quinazolinones were perfomed. A synthesis of 2-methyl-3-substituted quinazolinones was performed in natural deep eutectic solvents, while 3-aryl quinazolinones were obtained by using microwave assisted synthesis. Benzoxazinone, which was used as an intermediate in the synthesis of 2-methyl-3-substituted quinazolinones, was prepared conventionally from anthranilic acid and acetic anhydride. In order to find the most appropriate synthetic path, twenty natural deep eutectic solvents were applied as a solvent in these syntheses. Choline chloride:urea (1: 2) was found to be the most efficient solvent and was further used in the synthesis of 2-methyl quinazolinone derivatives (2–12). 3-Aryl quinazolinones (13–17), on the other hand, were synthesized in one-pot microwave-assisted reaction of anthranilic acid, different amines and trimethyl orthoformate. All compounds were synthesized in good to excellent yields, characterized by LC-MS/MS spectrometry and 1H- and 13C-NMR spectroscopy.

Preparation of 4(3H)-quinazolinones from aryldiazonium salt, nitriles and 2-aminobenzoate via a cascade annulation

One-pot synthesis of 3-aryl-4(3H)-quinazolinones has been realized through a cascade annulation. Reaction of aryldiazonium salt with a nitrile provides in situ generation of a reactive nitrilium ion, which is attacked by the amino group of 2-aminobenzoate followed by cyclization to deliver the desired product. This strategy offers a convenient and easy access to a wide range of functionalized quinazolinone.

Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation

A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted both as a solid CO source and a reductant. Notably, methaqualone as a sedative and hypnotic medication can be prepared easily in 68% yield (4b) under our conditions as well.

FeCl3-catalyzed tandem condensation/intramolecular nucleophilic addition/C-C bond cleavage: A concise synthesis of 2-substitued quinazolinones from 2-aminobenzamides and 1,3-diketones in aqueous media

A concise approach for the synthesis of 2-substituted quinazolinones using an iron-catalyzed tandem reaction of 2-aminobenzamides with acyclic or cyclic 1,3-diketones via condensation, intramolecular nucleophilic addition, C-C bond cleavage in an aqueous solution of poly(ethylene glycol) under oxidant-free conditions has been developed.

Synthesis, biological evaluation and structure-activity relationship of 2-styrylquinazolones as anti-tubercular agents

2-Styrylquinazolones are reported as a novel class of potent anti-mycobacterial agents. Forty-six target compounds have been synthesized using one pot reaction involving isatoic anhydride, amine, and triethyl orthoacetate followed by aldehyde to construct

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

Copper-Catalyzed Tandem Reaction of 2-Aminobenzamides with Tertiary Amines for the Synthesis of Quinazolinone Derivatives

We developed a copper-catalyzed tandem reaction of 2-aminobenzamides with tertiary amines for the formation of quinazolinone derivatives. The strategy includes two steps (cyclization and coupling) performed in one pot. A number of substrates reacted well under standard conditions to give the corresponding quinazolinone derivatives in moderate to good yields.

The reaction of 2-(acylamino)benzonitriles with primary aromatic amines: A convenient synthesis of 2-substituted 4-(arylamino)quinazolines

Abstract 2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.

Br?nsted acid-catalyzed selective C-C bond cleavage of 1,3-diketones: A facile synthesis of 4(3H)-quinazolinones in aqueous ethyl lactate

A facile and green approach was developed for the synthesis of 4(3H)-quinazolinones by using camphorsulfonic acid as a catalyst in an aqueous solution of biodegradable ethyl lactate. Various 2-aryl-, 2-alkyl-, and 2-(4-oxoalkyl)quinazolinones were obtained by cyclization of 2-aminobenzamides with a wide range of acyclic or cyclic 1,3-diketones via C-C bond cleavage in satisfactory to excellent yields.