340-57-8

Basic information

• Product Name: mecloqualone
• Synonyms: mecloqualone;3-(2-Chlorophenyl)-2-methylquinazolin-4(3H)-one;CHI-8;NSC-142005;W 4744;W-4744;3-(2-chlorophenyl)-2-methyl-quinazolin-4-one;3-(2-chlorophenyl)-2-methylquinazolin-4-one
• CAS NO: 340-57-8
• Molecular Formula: C₁₅H₁₁ClN₂O
• Molecular Weight: 270.73
• EINECS: 206-432-8
• Mol File: 340-57-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 126-128°
• Boiling Point: 421.7°C at 760 mmHg
• Flash Point: 208.9°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 2.55E-07mmHg at 25°C
• Refractive Index: 1.647
• PKA: 1.66±0.70(Predicted)
• CAS DataBase Reference: mecloqualone(CAS DataBase Reference)
• NIST Chemistry Reference: mecloqualone(340-57-8)
• EPA Substance Registry System: mecloqualone(340-57-8)

Safety Data

• Hazardous Substances Data: 340-57-8(Hazardous Substances Data)

Usage

Uses

Sedative-hypnotic.

Hazard

Moderately toxic by ingestion.

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

Upstream product

• 95-51-2 o-chloroaniline 
• 89-52-1 o-acetylamino-benzoic acid 
• 137-04-2 2-chloroaniline hydrochloride 
• 25116-00-1 2-acetamidobenzonitrile 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 118-92-3 anthranilic acid 
• 1021007-50-0 2-chloro-N-(2-nitro-benzyl)-aniline 
• 552-89-6 2-nitro-benzaldehyde 
• 118-48-9 isatoic anhydride 
• 78-39-7 Triethyl orthoacetate 
• 50622-99-6 2-nitro-benzoic acid-(2-chloro-anilide) 
• 838-77-7 2-amino-N-(o-chlorophenyl)benzamide 
• 552-16-9 ortho-nitrobenzoic acid 
• 610-14-0 2-nitrobenzyl chloride 

Downstream Products

• 73283-21-3 2-[2-Oxo-2-(2-pyridyl)ethyl]-3-o-chlorophenyl-4(3H)-quinazolinone 
• 73283-22-4 2-[2-Oxo-2-(3-pyridyl)ethyl]-3-o-chlorophenyl-4(3H)-quinazolinone 
• 73283-23-5 2-[2-oxo-2-(4-pyridyl)ethyl]-3-o-chlorophenyl-4(3H)-quinazolinone 
• 596807-50-0 2-(3-chloro-2-oxo-propyl)-3-(2-chloro-phenyl)-3H-quinazolin-4-one 
• 73283-20-2 2-(3,3,3-Trifluoroacetonyl)-3-o-chlorophenyl-4(3H)-quinazolinone 
• 514830-27-4 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid N'-[3-(2-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylmethyl]-hydrazide 
• 514830-29-6 3-(4-dimethylamino-phenyl)-acrylic acid N'-[3-(2-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylmethyl]-hydrazide 
• 514830-30-9 3-(4-methoxy-phenyl)-acrylic acid N'-[3-(2-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylmethyl]-hydrazide 
• 514830-28-5 3-phenyl-acrylic acid N'-[3-(2-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylmethyl]-hydrazide 
• 514830-23-0 acetic acid N'-[3-(2-chloro-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-ylmethyl]-hydrazide 
• 514830-19-4 3-(2-chloro-phenyl)-2-hydrazinomethyl-3H-quinazolin-4-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.

Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: Synthesis of natural products and drugs

A mild and greener protocol was developed to synthesize substituted quinazolinones and dihydroquinazolinones via deep eutectic solvent (DES) mediated cyclization with a series of aliphatic, aromatic, and heteroaromatic aldehydes in good to excellent yields. This greener strategy was further utilised to synthesize various quinazolinone natural products and drugs.

Convenient synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones: Applications towards the synthesis of drugs

Simple, convenient, and green synthetic protocols have been developed for the one pot synthesis of 2,3-disubstituted quinazolin-4(3H)-ones and 2-styryl-3-substituted quinazolin-4(3H)-ones under catalyst and solvent free conditions. The multicomponent reaction (3-MCR) involving isatoic anhydride, an amine, and orthoester afforded the 2,3-disubstituted quinazolin-4(3H)-ones in excellent yields under classical heating at 120 °C for 5 h or under microwave irradiation at 140°C for 20-30 min. The use of ammonium acetate instead of the amine provides the 2-substituted quinazolin-4(3H)-ones. The reactions are compatible with various substituted isatoic anhydrides, aryl/heteroaryl/alkyl/cycloalkyl amines, and orthoesters. The strategies are extended to the one pot tandem condensation involving isatoic anhydride, an amine, orthoester, and aldehyde to afford highly functionalized (E)-3-aryl/heteroaryl-2-styrylquinazolin/(2-(heteroaryl)vinyl)quinazolin-4(3H)-ones. The applications of the methodologies are demonstrated through the synthesis of various drugs which act on the central nervous system such as methaqualone, mebroqualone, mecloqualone, piriquialone, and diproqualone.