32606-03-4

Usage

Chemical structure

A unique structure consisting of a quinoline ring with three methyl groups and a dione group.

Vibrant color

Exhibits a strong and intense color, making it suitable for use as a pigment in various industries.

High stability

Resistant to various environmental factors, such as light, heat, and moisture, which contributes to its widespread use in dyes, inks, and coatings.

Pharmaceutical potential

Studied for its potential anti-cancer and anti-inflammatory properties, indicating possible applications in the development of new drugs.

Organic synthesis intermediate

Serves as a building block for a variety of chemical reactions and products, making it valuable in the field of organic chemistry.

Diverse applications

Used in various industries, including the manufacturing of dyes, inks, coatings, and potentially pharmaceuticals.

Molecular weight

Approximately 207.25 g/mol

Appearance

Yellow to orange crystalline solid

Solubility

Soluble in organic solvents such as ethanol, methanol, and acetone, but less soluble in water.

InChI:InChI=1/C12H13NO2/c1-12(2)10(14)8-6-4-5-7-9(8)13(3)11(12)15/h4-7H,1-3H3

Upstream product

• 70254-43-2 4-Hydroxy-2-quinolone 
• 74-88-4 methyl iodide 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 10328-92-4 N-Methylisatoic anhydride 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 106875-07-4 3,3-dimethylquinoline-2,4(1H,3H)-dione 
• 118-48-9 isatoic anhydride 
• 27667-34-1 4-methoxyquinolin-2(1H)-one 
• 1677-46-9 4-hydroxy-1-methyl-2(1H)-quinolone 

Downstream Products

• 53207-57-1 4-hydroxy-1,3,3-trimethyl-3,4-dihydro-1H-quinolin-2-one 

Relevant academic research and scientific papers

2,2,2-trifluoroethanol-promoted access to symmetrically 3,3-disubstituted quinoline-2,4-diones

The unprecedented use of 2,2,2-trifluoroethanol as reaction solvent provided a facile and convenient access to symmetrically 3,3-disubstitued quinoline-2,4-diones in moderate to excellent yields and high regioselectivity, by reaction of 4-hydroxy-2-quinolones with electrophiles like methyl iodide, as well as benzyl and allyl bromides in the presence of K2CO3. Silver (I) oxide is required to increase the yield of the methylations.

Reductive coupling of isatins with ketones and aldehydes by low-valent titanium

The reductive coupling of isatins with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydoxy-3-(1-hydoxyalkyl)oxindoles and 3-alkylideneoxindoles, selectively by controlling the reaction conditions. Alt

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.

4-IMIDAZOLYL-1,2,3,4-TETRAHYDROQUINOLINE DERIVATIVES AND THEIR USE AS ALDOSTERONE/11-BETA-HYDROXYLASE INHIBITORS

The present invention provides a compound of formula (I), said compound is inhibitor of aldosterone synthase, and/or 11beta-hydroxylase (CYP11B1), and thus can be employed for the treatment of a disorder or disease mediated by aldosterone synthase and/or CYP11B1. Finally, the present invention also provides a pharmaceutical composition.

One-step Synthesis for the Preparation of Quinoline Alkaloid Analogues

(Matrix Presented) A new one-step methodology has been introduced for the synthesis of quinoline alkaloid analogues. The reaction is based on a modification of the Mukaiyama aldol condensation, making use of the high reactivity of lactones or anhrydrides. The reaction is general and allows for the construction of new hetero polycondenced molecules in a one-step synthesis.

Methylation of 4-Hydroxy-2-quinolone

The reaction of 4-hydroxy-2-quinolone (1a) with methyl iodide/potassium hydroxide in boiling acetone gave a mixture of 1-methyl-4-methoxy-2-quinolone (1d), 1,3-dimethyl-4-methoxy-2-quinolone (1e), and 1,3,3-trimethyl-2,4-dioxo-1,2,3,4-tetrahydroquinoline (2).As by-product 2,4-dimethoxyquinoline (3) was identified.Under the same conditions 4-methoxy-2-quinolone (1c) yielded 1d, 1e, 2 and 3, while 1-methyl-4-hydroxy-2-quinolone (1b) gave 1d, 1e and 2.