56600-90-9

Usage

Uses

Used in Pharmaceutical Industry:
4-(6-Methoxy-2-naphthalenyl)-3-buten-2-one is used as a precursor for the synthesis of Nabumetone (N200500), which is an anti-inflammatory and antibacterial agent. Its role in the production of Nabumetone is crucial, as it contributes to the drug's effectiveness in treating conditions such as arthritis, ankylosing spondylitis, and other inflammatory disorders.
As a chemical intermediate, 4-(6-Methoxy-2-naphthalenyl)-3-buten-2-one may also have potential applications in the development of other pharmaceuticals, although the provided materials do not specify these additional uses. Its reactivity and structural features make it a valuable compound for further research and development in the pharmaceutical sector.

InChI:InChI=1/C15H14O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h3-10H,1-2H3/b4-3+

Upstream product

• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 78-94-4 methyl vinyl ketone 
• 3453-33-6 6-methoxynaphthalene-2-carbaldehyde 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 73356-31-7 4-(6-methoxy-2-naphthalenyl)-4-hydroxybut-3-en-2-one 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 15231-91-1 6-bromo-naphthalen-2-ol 
• 16239-18-2 1,6-dibromo-2-naphthol 
• 135-19-3 β-naphthol 
• 220786-56-1 (±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone 
• 67-64-1 acetone 

Downstream Products

• 1258422-88-6 (1S,6R)-1'-benzyl-6-(6-methoxynaphthalen-2-yl)-2-methylspiro[cyclohex[2]ene-1,3'-indoline]-2',4-dione 
• 65726-31-0 3,4,5-Trimethoxy-benzoic acid 3-(6-methoxy-naphthalen-2-yl)-1-methyl-propyl ester 
• 42924-53-8 nabumetone 

Relevant academic research and scientific papers

Organocatalytic diastereo- And enantioselective oxa-hetero-Diels-Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans

Tetrahydropyran derivatives are found in bioactives, and introduction of the trifluoromethyl group into molecules often improves biofunctions. Here we report diastereo- and enantioselective oxa-hetero-Diels-Alder reactions catalyzed by amine-based catalyst systems that afford trifluoromethyl-substituted tetrahydropyranones. Catalyst systems and conditions suitable for the reactions to provide the desired diastereomer products with high enantioselectivities were identified, and various trifluoromethyl-substituted tetrahydropyranones were synthesized with high diastereo- and enantioselectivities. Mechanistic investigation suggested that the reactions involve a [4 + 2] cycloaddition pathway, in which the enamine of the enone acts as the diene and the ketone carbonyl group of the aryl trifluoromethyl ketone acts as the dienophile. In this study, tetrahydropyran derivatives with the desired stereochemistry that are difficult to synthesize by previously reported methods were concisely obtained, and the range of tetrahydropyran derivatives that can be synthesized was expanded. This journal is

A CATALYST FOR ONE POT SYNTHESIS OF NABUMETONE AND PROCESS OF PREPARATION THEREOF

The present invention relates to novel heterogeneous catalyst composition for selective synthesis of Nabumetone in one pot process and process to prepare the catalyst. The present invention provides a novel catalyst comprises of Lanthanum, Magnesium, and Nickel particles doped on specific type of silica support, preferably that the support is in amorphous nature. The catalyst is having bifunctional condensation and hydrogenation properties for one pot synthesis of Nabumetone comprising of: Nickel and Lanthanum-magnesium mixed oxide on support of mesoporous silica; Wherein 25 to 30 % w/w of Lanthanum-magnesium mixed oxide are entrapped in pores and surface of support is coated with 3 to 5% w/w Nickel with the result that it prevent the leaching of Lanthanum-magnesium mixed oxide in reaction medium and provides reusability of catalyst.

A scalable two-step continuous flow synthesis of nabumetone and related 4-aryl-2-butanones

Three different continuous flow strategies for the generation of important 4-aryl-2-butanone derivatives including the anti-inflammatory drug nabumetone [4-(6-methoxy-2-naphthalenyl)-2-butanone] and the aroma compounds raspberry ketone [4-(4-hydroxyphenyl)-2-butanone] and its methyl ether [4-(4-methoxyphenyl)-2-butanone] were evaluated. All three protocols involve the initial preparation of the corresponding 4-aryl-3-buten-2-ones via Mizoroki-Heck, Wittig, or aldol strategies, which is then followed by selective hydrogenation of the C=C double bond to the desired 4-aryl-2-butanones. The synthetic routes to 4-aryl-3-buten-2-ones were first optimized/intensified on small scale to reaction times of 1-10 min using batch microwave heating technology and then translated to a scalable continuous flow process employing commercially available stainless steel capillary tube reactors. For the synthesis of 4-(4-methoxyphenyl)-3-buten-2-one a further scale-up using a custom-built mesofluidic mini-plant flow system capable of processing several liters per hour was designed to further expand the scale of the process. The final hydrogenation step was performed using a fixed-bed continuous flow hydrogenator employing Ra/Ni as a catalyst.

Process research and structural studies on nabumetone

A short, simple and economical process for large-scale preparation of nabumetone has been developed. The single-crystal structures of nabumetone and one of its key intermediates have been determined by X-ray diffraction studies. Two impurities have been isolated and characterised.

Production of nabumetone or precursors thereof

In producing nabumetone or precursor thereof, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl bromide or methyl chloride, in a halogen-free liquid solvent comprising at least about 40% by weight of one or more compounds of the formula RZ where R is a hydrogen atom or an alkyl group, and Z is a hydroxyl group or a cyanide group with the proviso that if Z is a cyanide group, R is an alkyl group, and in the presence of at least one strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed. The 6-bromo-2-naphthol in turn is preferably formed by reacting 1,6-dibromo-2-naphthol with hydrogen in a halogen-containing liquid solvent comprising at least about 50% by weight of (A) at least one liquid organic halide solvent in which the halogen content has an atomic number of 35 or less or (B) a mixture of water and at least one such liquid organic halide solvent, and in the presence of catalytic amounts of (i) a tungsten carbide-based catalyst, and (ii) at least one phase transfer catalyst, most preferably while purging HBr from the reaction mixture as it is formed. In this way, the quantities of by-products formed in the overall operation are reduced, the need for use of excess iron and/or dimethyl sulfate as reaction components is avoided, and the overall efficiency of plant operation is improved especially when conducted on a large scale.