1788-93-8

Basic information

• Product Name: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon
• Synonyms: 2-methyl-3-(4’-chlorphenyl)chinazolon-(4);2-methyl-3-(4-chlorophenyl)-4(3h)-quinazolinone;3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon;2-methyl-3-(4-chlorophenyl)quinazolin-4-one
• CAS NO: 1788-93-8
• Molecular Formula: C₁₅H₁₁ClN₂O
• Molecular Weight: 270.71364
• Mol File: 1788-93-8.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 439°Cat760mmHg
• Flash Point: 219.3°C
• Appearance: /
• Density: 1.2576 (rough estimate)
• Vapor Pressure: 6.6E-08mmHg at 25°C
• Refractive Index: 1.6330 (estimate)
• CAS DataBase Reference: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon(1788-93-8)
• EPA Substance Registry System: 3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon(1788-93-8)

Safety Data

• Hazardous Substances Data: 1788-93-8(Hazardous Substances Data)

Usage

General Description

3-(p-chlorophenyl)-2-methyl-4(3h)-quinazolinon, also known as pirenzepine, is a chemical compound that belongs to the quinazolinone class. It has been studied for its potential use as an antagonist of the muscarinic acetylcholine receptors. Pirenzepine has been found to have a high affinity for the M1 subtype of muscarinic receptors, and has been investigated for its potential use in the treatment of peptic ulcers, as well as its potential as a cognitive enhancer. Additionally, it has been studied for its potential use in the treatment of chronic obstructive pulmonary disease and other respiratory conditions. Pirenzepine's chemical structure and properties make it a promising candidate for further research and development in the area of therapeutics targeting muscarinic receptors.

InChI:InChI=1/C15H11ClN2O.ClH/c1-10-17-14-5-3-2-4-13(14)15(19)18(10)12-8-6-11(16)7-9-12;/h2-9H,1H3;1H

Upstream product

• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 106-47-8 4-chloro-aniline 
• 20265-96-7 p-chloroaniline hydrochloride 
• 25116-00-1 2-acetamidobenzonitrile 
• 108-88-3 toluene 
• 89-52-1 o-acetylamino-benzoic acid 
• 7719-12-2 phosphorus trichloride 
• 118-48-9 isatoic anhydride 
• 78-39-7 Triethyl orthoacetate 
• 4943-86-6 2-amino-N-(4-chlorophenyl)benzamide 
• 118-92-3 anthranilic acid 
• 75-16-1 methylmagnesium bromide 
• 622403-43-4 2-(4-Chloro-phenyliminomethyleneamino)-benzoic acid ethyl ester 
• 179039-70-4 ethyl 2-(triphenylphosphoranylidene-amino)benzoate 

Downstream Products

• 128457-98-7 3-(4-Chloro-phenyl)-2-((E)-3-oxo-3-p-tolyl-propenyl)-3H-quinazolin-4-one 
• 128457-94-3 3-(4-Chloro-phenyl)-2-((E)-3-oxo-3-phenyl-propenyl)-3H-quinazolin-4-one 
• 80806-72-0 3-(4-Chloro-phenyl)-2-[(E)-2-(4-hydroxy-3-nitro-phenyl)-vinyl]-3H-quinazolin-4-one 
• 81541-41-5 3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazoline-2-carbaldehyde 
• 61554-51-6 2-Bromomethyl-3-(4-chloro-phenyl)-3H-quinazolin-4-one 
• 596807-51-1 2-(3-chloro-2-oxo-propyl)-3-(4-chlorophenyl)-3H-quinazolin-4-one 
• 596807-56-6 3-(4-chloro-phenyl)-2-(3-hydrazino-2-oxo-propyl)-3H-quinazolin-4-one 
• 80884-23-7 3-(4-Chloro-phenyl)-2-[(2,4-dimethyl-benzylamino)-methyl]-3H-quinazolin-4-one 
• 80884-16-8 3-(4-Chloro-phenyl)-2-[(2-p-tolyl-ethylamino)-methyl]-3H-quinazolin-4-one 
• 80884-18-0 3-(4-Chloro-phenyl)-2-{[2-(4-chloro-phenyl)-ethylamino]-methyl}-3H-quinazolin-4-one 
• 80884-21-5 3-(4-Chloro-phenyl)-2-[(2,4-dichloro-benzylamino)-methyl]-3H-quinazolin-4-one 
• 131532-76-8 C₁₆H₁₂ClN₅OS 
• 131532-77-9 C₁₇H₁₄ClN₅OS 
• 131532-78-0 C₁₉H₁₆ClN₅OS 

Relevant articles and documents

Microwae-assisted one-pot three component synthesis of some new 4(3H)-quinazolinone derivatives

Efficient microwave-assisted synthesis of 4(3H)-quinazolinones by the one-pot three-component condensation of isatoic anhydride, primary amines and orthoesters in the presence of catalytic amounts of p-toluenesulfonic acid in high yields is reported.

A novel superparamagnetic powerful guanidine-functionalized γ-Fe2O3based sulfonic acid recyclable and efficient heterogeneous catalyst for microwave-assisted rapid synthesis of quinazolin-4(3H)-one derivatives in Green media

The novel organic-inorganic nanohybrid superparamagnetic (γ-Fe2O3@CPTMS-guanidine@SO3H) nanocatalyst modified with sulfonic acid represents an efficient and green catalyst for the one-pot synthesis of quinazolin-4(3H)-one derivativesviathree-component condensation reaction between anthranilic acid, acetic anhydride and different amines under microwave irradiation and solvent-free conditions (4a-q). XRD, FT-IR, FE-SEM, TGA, VSM and EDX were used to characterize this new magnetic organocatalyst. Outstanding performance, short response time (15-30 min), simple operation, easy work-up procedure, and avoidance of toxic catalysts can be regarded as its significant advantages. Moreover, it can be easily separated from the reaction solution through magnetic decantation using an external magnet, and recycled at least six times without notable reduction in its activity.

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.

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.