519-66-4

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-1-methyl-3-phenyl-1,2-dihydroquinolin-2-one is used as a pharmacophore for drug design and development due to its unique structure and functional groups. Its potential as a lead compound in the creation of new medications can be explored, particularly for targeting specific biological pathways or receptors.
Used in Chemical Synthesis:
In the chemical industry, 4-hydroxy-1-methyl-3-phenyl-1,2-dihydroquinolin-2-one serves as a building block for the synthesis of other chemical compounds. Its versatile structure allows for further modification and functionalization, making it a valuable intermediate in the development of novel chemical entities with various applications.
Used in Medical Research:
4-Hydroxy-1-methyl-3-phenyl-1,2-dihydroquinolin-2-one is utilized in medical research for studying its biological properties and potential therapeutic effects. Researchers can investigate its interactions with biological systems, its pharmacological profile, and its safety and efficacy in treating specific diseases or conditions.

InChI:InChI=1/C16H13NO2/c1-17-13-10-6-5-9-12(13)15(18)14(16(17)19)11-7-3-2-4-8-11/h2-10,18H,1H3

Upstream product

• 83-13-6 diethyl 2-phenylmalonate 
• 100-61-8 N-methylaniline 
• 144603-33-8 3-chloro-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 10387-40-3 potassium thioacetate 
• 103-80-0 phenylacetyl chloride 
• 149-30-4 2-Mercaptobenzothiazole 
• 31491-20-0 (1-ethoxy-2-phenylvinyloxy)trimethylsilane 
• 10328-92-4 N-Methylisatoic anhydride 
• 1859-76-3 2-(methylamino)benzophenone 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 85-91-6 Methyl N-methylanthranilate 
• 521980-39-2 1-methyl-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanate 
• 342598-46-3 N-(2-benzoylphenyl)-2,2,2-trichloro-N-methylacetamide 
• 401635-58-3 3-bromo-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 

Downstream Products

• 80356-42-9 4-Amino-1-methyl-3-phenyl-chinolin-2(1H)-on 
• 83609-72-7 5-Methyl-11-phenyl-isochinolino<4,3-c>chinolin-6(5H)-on 
• 56857-90-0 4-Chloro-1-methyl-2-oxo-3-phenyl-1,2-dihydroquinoline 
• 144603-33-8 3-chloro-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 113737-84-1 3-hydroxy-1-methyl-3-phenylquinoline-2,4(1H,3H)-dione 
• 94298-57-4 3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one 
• 1447565-10-7 3-butyl-1'-methyl-2-phenyl-2',4'-dihydro-1'H-spiro[indene-1,3'-quinoline]-2',4'-dione 
• 1447565-37-8 6-butyl-1-methyl-3,5-diphenylpyrano[2,3,4-de]quinolin-2(1H)-one 
• 1447565-08-3 1'-methyl-2,3-diphenyl-2',4'-dihydro-1'H-spiro[indene-1,3'-quinoline]-2',4'-dione 
• 1447565-32-3 1-methyl-3,5,6-triphenylpyrano[2,3,4-de]quinolin-2(1H)-one 
• 1447565-50-5 1-methyl-3-phenyl-5-((phenylsulfonyl)methyl)-1H-furo[2,3,4-de]quinolin-2(5H)-one 
• 1447565-46-9 12-methyl-6-[(phenylsulfonyl)methyl]-6H-isochromeno[4,3-c]quinolin-11(12H)-one 
• 1447565-45-8 2-(12-methyl-11-oxo-11,12-dihydro-6H-isochromeno[4,3-c]quinolin-6-yl)acetonitrile 
• 1447565-49-2 2-(1-methyl-2-oxo-3-phenyl-2,5-dihydro-1H-furo[2,3,4-de]quinolin-5-yl)acetonitrile 

Relevant academic research and scientific papers

Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones

In this study, a 50-membered library of substituted 4-hydroxyquinolin-2(1H)-ones and two closely related analogues was designed, scored in-silico for drug likeness and subsequently synthesized. Thirteen derivatives, all sharing a common 3-phenyl substituent showed minimal inhibitory concentrations against Mycobacterium tuberculosis H37Ra below 10 μM and against Mycobacterium bovis AN5A below 15 μM but were inactive against faster growing mycobacterial species. None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as the most promising member of the library with a MIC of 3.2 μM and a CC50 against MRC-5 of 67.4 μM.

Stereochemistry of the reduction of α-chloroketones with sodium borohydride—application to 3-chloroquinoline-2,4-diones: Dedicated to the memory of Professor Dr.?Vojeslav ?těrba who died in September 2015 being nearly 93 years old

3-Chloroquinoline-2,4-diones were reduced with sodium borohydride to give syn- and anti-chlorohydrins, the stereochemistry of which was established by NMR spectroscopy. Both stereoisomeric chlorohydrins were reacted with potassium carbonate in methanol. a

Oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones into N-(α-ketoacyl)anthranilic acids Dedicated to Professor Slovenko Polanc on his 65th birthday

N-(α-Ketoacyl)anthranilic acids were prepared by oxidative ring opening of 3-hydroxyquinoline-2,4(1H,3H)-diones by using paraperiodic acid (H5IO6) or sodium periodate (NaIO4). The optimisation of the reaction conditions is

Catalyst-controlled divergent C-H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds with alkynes and alkenes

Achieving site-selective, switchable C-H functionalizations of substrates that contain several different types of reactive C-H bonds is an attractive objective to enable the generation of different products from the same starting materials. Herein, we dem

Reaction of some 2-quinolone derivatives with phosphoryl chloride: Synthesis of novel phosphoric acid esters of 4-hydroxy-2-quinolone

3-Chloroquinoline-2,4-diones do not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized by 1H and 13C NMR, IR, EI-MS, and ESI-MS spectroscopy, and in select cases by 31P NMR spectroscopy.

Modified mukaiyama reaction for the synthesis of quinoline alkaloid analogues: Total synthesis of 3,3-diisopentenyl-N-methylquinoline-2,4-dione

A general synthetic approach, capable of accessing a diverse range of 3,3-disubstituted quinoline-2,4-diones and 1,8-naph-thyridine-2,4-diones via titanium tetrachloride catalyzed C-acylation of silyl ketene acetals is described. The suggested methodological platform is surveyed using different reaction conditions and is applied to the total syntheses of 3,3-diisopentenyl-N-methylquinoline-2,4-dione and 3-demethyl-N-methylatanine.

Synthesis of coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolinones by tellurium-triggered cyclizations

Coumarins, 4-hydroxycoumarins, and 4-hydroxyquinolin-2(1H)-ones can be conveniently prepared by treatment of α-halocarboxylic acid esters of salicylaldehyde, o-hydroxyacetophenone, methyl salicylate, and methyl N-methyl- or N-phenylanthranilates with sodium or lithium telluride. Phenylketene formation competes with cyclization of the α-chlorophenylacetate ester of methyl salicylate as demonstrated by a trapping experiment with benzylamine. Elemental tellurium may be recovered and reused.

Novel tandem hydration/cyclodehydration of α-thiocyanatoketones to 2-oxo-3-thiazolines. Application, to thiazolo[5,4-c]quinoline-2}4(3aH,5H)-dione synthesis

Novel tandem hydration of α-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]-thiazolo[5,4-c]quinoline-2, 4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as both corresponding 2,3-dioxo-1,2,3,4-tetrahydroquinolin-3-yl thiocyanates (2) and S-(2,4-dioxo-1,2,3,4-tetrahydroquinolin-3-yl) thiocarbamates (3) rapidly hydrolyze in the presence of water to 4-hydroxyquinolin-2(1H)-ones (1).

Electrosynthesis of 3-chloro-1,4-disubstituted-2(1H)-quinolinones and 3,3-dichloro-4-hydroxy-1,4-disubstituted-3,4-dihydro-2(1H)-quinolinones, as well as a new convenient process to dioxindoles

Cathodic reduction of N-(2-acyl(or aroyl)phenyl)-2,2,2,-trichloro-N-alkylacetamide at - 1.2 V (vs SCE) under aprotic conditions yields 3-chloro-1,4-disubstituted-2(1H)-quinolinones (1) as the major product. When the reaction is carried out at -0.8 V (vs S

1-Methyl-3-phenyl-3-thiocyanato-1H,3H-quinoline-2,4-dione: A Novel Thiocyanating Agent

Under mild reaction conditions, the thiocyanato group is selectively transferred from 1-methyl-3-phenyl-3-thiocyanato-1H,3H-quinoline-2,4-dione (3) to some nucleophiles. Aliphatic primary and secondary amines are converted to S-cyanothiohydroxylamines, anilines afford p-thiocyanatoanilines, Wittig reagent is thiocyanated in α-position, and thiols are oxidized to disulfides.