16064-27-0

Basic information

• Product Name: 8-METHOXY-4-QUINAZOLONE
• Synonyms: 8-METHOXY-4-QUINAZOLONE;8-Methoxyquinazolin-4(3H)-one;8-Methoxyquinazolin-4-ol;8-Methoxy-4(1H)-quinazolinone;4-Hydroxy-8-Methoxyquinazoline;8-methoxyquinazolin-4(1H)-one
• CAS NO: 16064-27-0
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Mol File: 16064-27-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 298-300℃ (methanol )
• Boiling Point: 340.0±44.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.93±0.20(Predicted)
• CAS DataBase Reference: 8-METHOXY-4-QUINAZOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-METHOXY-4-QUINAZOLONE(16064-27-0)
• EPA Substance Registry System: 8-METHOXY-4-QUINAZOLONE(16064-27-0)

Safety Data

• Hazardous Substances Data: 16064-27-0(Hazardous Substances Data)

Usage

General Description

8-Methoxy-4-quinazolone is a chemical compound with the molecular formula C9H7NO2. It is a derivative of quinazoline, a heterocyclic compound composed of two fused six-membered rings containing a nitrogen atom. This specific derivative contains a methoxy group attached to the carbon atom at position 8 of the quinazolone ring. 8-Methoxy-4-quinazolone has potential applications in the pharmaceutical industry, particularly as a building block for the synthesis of pharmaceutical compounds and as a precursor in organic chemistry. Its structure and properties make it a valuable tool in drug discovery and development.

Upstream product

• 3177-80-8 2-amino-3-methoxybenzoic acid 
• 77287-34-4 formamide 
• 18503-89-4 N,N-dimethylformamide diisopropyl acetal 
• 106782-78-9 3-methoxy-2-aminobenzamide 
• 5121-34-6 methyl 2-amino-3-methoxybenzoate 

Downstream Products

• 90417-38-2 8-hydroxy-2-methyl-4(3H)-quinazolinone 
• 154288-09-2 4-chloro-8-methoxyquinazoline 

Relevant articles and documents

A in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method

The invention discloses a in the aqueous phase under microwave conditions using halogenated benzamide fast synthesis of quinazoline compounds of the method, the use of palladium chloride to serve as the catalyst, in water under microwave heating conditions, neighbouring halogen benzamide with an isocyanate reaction to produce the quinazoline compounds of the method, the invention an environment-friendly, the operation is simple, cheap and safe, efficient process for producing quinazoline compounds of the method. Compared with the prior art, this method not only can be applied to a large number of functional groups, the productive rate is high, few by-products, and the operation is simple, safe, low cost, environmental protection.

Optimization of a Novel Quinazolinone-Based Series of Transient Receptor Potential A1 (TRPA1) Antagonists Demonstrating Potent in Vivo Activity

There has been significant interest in developing a transient receptor potential A1 (TRPA1) antagonist for the treatment of pain due to a wealth of data implicating its role in pain pathways. Despite this, identification of a potent small molecule tool possessing pharmacokinetic properties allowing for robust in vivo target coverage has been challenging. Here we describe the optimization of a potent, selective series of quinazolinone-based TRPA1 antagonists. High-throughput screening identified 4, which possessed promising potency and selectivity. A strategy focused on optimizing potency while increasing polarity in order to improve intrinisic clearance culminated with the discovery of purinone 27 (AM-0902), which is a potent, selective antagonist of TRPA1 with pharmacokinetic properties allowing for >30-fold coverage of the rat TRPA1 IC50 in vivo. Compound 27 demonstrated dose-dependent inhibition of AITC-induced flinching in rats, validating its utility as a tool for interrogating the role of TRPA1 in in vivo pain models.

N3-Alkylation during formation of quinazolin-4-ones from condensation of anthranilamides and orthoamides

Dimethylformamide dimethylacetal (DMFDMA) is widely used as a source of electrophilic one-carbon units at the formate oxidation level; however, electrophilic methylation with this reagent is previously unreported. Reaction of anthranilamide with DMFDMA at 150 °C for short periods gives mainly quinazolin-4-one. However, prolonged reaction with dimethylformamide di(primary-alkyl)acetals leads to subsequent alkylation at N3. 3-Substituted anthranilamides give 8-substituted 3-alkylquinazolin-4-ones. Condensation of anthranilamides with dimethylacetamide dimethylacetal provides 2,3-dimethylquinazolin-4-ones. In these reactions, the source of the N 3-alkyl group is the O-alkyl group of the orthoamides. By contrast, reaction with the more sterically crowded dimethylformamide di(isopropyl)acetal diverts the alkylation to the oxygen, giving 4-isopropoxyquinazolines, along with N3-methylquinazolin-4-ones where the methyl is derived from N-Me of the orthoamides. Reaction of anthranilamide with the highly sterically demanding dimethylformamide di(t-butyl)acetal gives largely quinazolin-4-one, whereas dimethylformamide di(neopentyl)acetal forms a mixture of quinazolin-4-one and N3-methylquinazolin-4-one. The observations are rationalised in terms of formation of intermediate cationic electrophiles (alkoxymethylidene-N,N-dimethylammonium) by thermal elimination of the corresponding alkoxide from the orthoamides. These are the first observations of orthoamides as direct alkylating agents.