1677-46-9

Basic information

• Product Name: 4-HYDROXY-1-METHYL-2-QUINOLONE
• Synonyms: AURORA KA-2363;4-HYDROXY-1-METHYL-2-QUINOLONE;4-HYDROXY-1-METHYL-1,2-DIHYDROQUINOLIN-2-ONE;4-HYDROXY-1-METHYL-1H-QUINOLIN-2-ONE;4-HYDROXY-1-METHYL-2(1H)-QUINOLONE;4-HYDROXY-N-METHYL-2-QUINOLONE;1-methyl-4-hydroxy-2-chinolinon;1-methyl-4-hydroxy-2-chinolon
• CAS NO: 1677-46-9
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• EINECS: 216-830-3
• Product Categories: Intermediates of Dyes and Pigments;Building Blocks;Heterocyclic Building Blocks;Quinolines
• Mol File: 1677-46-9.mol
• Article Data: 31

Chemical Properties

• Melting Point: 269-271 °C(lit.)
• Boiling Point: 306.47°C (rough estimate)
• Flash Point: 131.2°C
• Appearance: /
• Density: 1.326
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-HYDROXY-1-METHYL-2-QUINOLONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-1-METHYL-2-QUINOLONE(1677-46-9)
• EPA Substance Registry System: 4-HYDROXY-1-METHYL-2-QUINOLONE(1677-46-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: FG7350000
• Hazardous Substances Data: 1677-46-9(Hazardous Substances Data)

Usage

Uses

4-Hydroxy-1-methyl-2(1H)-quinolone was used as nucleophile in electrochemical oxidation of catechols and the reaction was studied by cyclic voltammetry and controlled-potential coulometry. It was used in ceric ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds to yield substituted dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones and dihydrofurophenalenones. It was used in the synthesis of :3-(4-methoxybenzyl)-4-hydroxy-1-methylquinolinone3-(benzo[d][1,3]dioxol-5-ylmethyl)-4-hydroxy-1-methylquinolin-2(1H)-one3-(4-chlorobenzyl)-4-hydroxy-1-methylquinolin-2(1H)-one3,3′-bis(4-chlorobenzylidene)-1,10-methylquinolin-2,20-(1H)-one

InChI:InChI=1/C10H9NO2/c1-11-8-5-3-2-4-7(8)9(12)6-10(11)13/h2-6,12H,1H3

Upstream product

• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 10328-92-4 N-Methylisatoic anhydride 
• 146828-46-8 1-methyl-2,4-dioxo-quinoline-3-carboxylic acid 
• 5946-42-9 methyl 2-(N-bromoacetyl-N-methylamino)benzoate 
• 39581-30-1 3-(N-methyl-N-phenylamino)-3-oxopropanenitrile 
• 115-18-4 2-methyl-3-buten-2-ol 
• 152628-30-3 3-Iod-N-methyl-4-tosyloxy-chinolin-2(1H)-on 
• 2922-83-0 L-kynurenine 
• 485-80-3 S-adenosyl-L-methionine 
• 73-32-5 L-isoleucine 
• 100-61-8 N-methylaniline 
• 105-53-3 diethyl malonate 

Downstream Products

• 50333-13-6 N-methylflindersine 
• 112547-35-0 N-methyl-3,3-dimethyl-2-methylen-2,3-dihydrofuro<3,2-c>chinolin-4-on 
• 112547-33-8 1,1-bis(N-methyl-4'-hydroxychinolin-2'-on-3'-yl)-3-methylbut-2-en 
• 106058-73-5 3,3'-benzylidenebis<4-hydroxy-1-methyl-2-quinolone> 
• 126936-71-8 1-Methyl-4-(2-oxo-2-p-tolyl-ethoxy)-1H-quinolin-2-one 
• 126936-72-9 4-[2-(4-Chloro-phenyl)-2-oxo-ethoxy]-1-methyl-1H-quinolin-2-one 
• 106058-75-7 3,3'-((4-methoxyphenyl) methylene) bis(4-hydroxy-1-methylquinolin-2(1H)-one) 
• 125215-67-0 4-hydroxy-1-methyl-3-(3-oxo-3-phenylpropyl)-1H-quinolin-2-one 
• 161185-37-1 4-hydroxy-6-methyl-3-phenyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione 
• 181937-62-2 4-Methyl-benzoic acid 1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl ester 
• 181937-67-7 4-Methoxy-benzoic acid 1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl ester 
• 211686-36-1 4-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one 
• 211686-40-7 3-cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one 
• 247237-54-3 3-((4-chlorophenyl)thio)-4-hydroxy-1-methylquinolin-2(1H)-one 

Relevant articles and documents

Synthesis of new quinolinones from 3-nitropyranoquinolinones

Alkaline hydrolysis of 3-nitropyranoquinolinones (6-alkyl-4-hydroxy-3-nitro-2H-pyrano[3,2-c]quinoline-2,5(6H)-diones) for different reaction times gave five products which were formed by the progressive degradation of the nitropyrano ring. Varying amounts of 3-nitroacetylquinolinones, quinolinones with side-chains of β- And β-ketoacids, quinolinone-3-carboxylic acids and 4-hydroxyquinolinones were isolated. With the aim of preparing new biologically active quinolone derivatives, the products of reaction of the 3-nitropyranoquinolinones with side-chains of α- And β-ketoacids with some nitrogen and carbon nucleophiles were also studied, some giving rise to annulated products.

Substituted quinolinones. Part 19. New and unexpected results from oxidation of 3-acetyl-1-alkyl- 4-hydroxyquinolin-2(1H)-ones using selenium dioxide

Oxidation of 3-acetyl-1-alkyl-4-hydroxyquinolin-2(1H)-ones using selenium dioxide under Riley conditions was described. The oxidation reaction produced a mixture of 2 unexpected α-keto acid and its dehydrated dimer derivatives. The oxidation reaction was studied under different reaction conditions in order to maximize the yields and optimize reaction conditions. Also, 1-alkyl-4-hydroxy-3-(2-nitroacetyl)quinolin-2(1H)-one and/or 3-acetyl-1-alkyl-4-diflouro-boryloxyquinolin-2(1H)-one derivatives were subjected to the same oxidation reaction giving rise improved reaction yields and selectivity in case of the boron-complex. Alkaline degradation of the dehydrated dimers led to formation of the 4-hydroxy-2-oxoquinoline-3-carboxylic acids while under the same conditions the α-keto acids underwent deoxalylation.

Rapid preparation of pyranoquinolines using microwave dielectric heating in combination with fractional product distillation

4-Hydroxy-6-methyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione was prepared by microwave-assisted cyclocondensation of N-methylaniline with 2 equiv of diethyl malonate. Key to the success of the synthesis was the use of open vessel controlled microwave heating technology, allowing the simultaneous removal of the formed ethanol from the reaction mixture by fractional distillation.

Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.

Novel Pyrazoloquinolin-2-ones: Design, synthesis, docking studies, and biological evaluation as antiproliferative EGFR-TK inhibitors

Two new series of diethyl 2-[2-(substituted-2-oxo-1,2-dihydroquinolin-4-yl)hydrazono]-succinates 6a-g and 1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazoles 7a-f have been designed and synthesized. The structures of the synthesized compounds were proved by IR, mass, NMR (2D) spectra and elemental analyses. The target compounds were evaluated for their in vitro cytotoxic activity against 60 cancer cell lines according to NCI protocol. Consequently, seven compounds were further examined against the most sensitive cell lines, leukemia CCRF-CEM, and MOLT-4. 5-Amino-1-(6-bromo-2-oxo-1,2-dihydroquinolin-4-yl)-1H-pyrazole-3,4-dicarbonitrile (7f) was the most active product, with IC50 = 1.35 uM and 2.42 uM against MOLT-4 and CCRF-CEM, respectively. Also, it showed a remarkable inhibitory activity compared to erlotinib on the EGFR TK with IC50 = 247.14 nM and 208.42 nM, respectively. Cell cycle analysis of MOLT-4 cells treated with 7f showed cell cycle arrest at G2/M phase (supported by Caspases, BAX and Bcl-2 studies) with a significant pro-apoptotic activity as indicated by annexin V-FITC staining. Moreover, the docking study indicated that both the pyrazole moiety and the quinolin-2-one ring showed good fitting into EGFR (PDB code: 1M17). In order to interpret SAR of the designed compounds, and provide a basis for further optimization, molecular docking of the synthesized compounds to known EGFR inhibitors was performed. The study illustrated the effect of several factors on the compounds’ activity.