Category: 5653-62-3

Wollenweber, Eckhard published the artcile8,2′-Dihydroxyflavone from Primula pulverulenta, Name: 2,3-Dimethoxybenzonitrile, the main research area is hydroxyflavone Primula.

A novel flavone, isolated from the farinose exudate of P. pulverulenta, was identified as 8,2′-dihydroxyflavone (I). This is the first naturally occurring flavone in which ring A is oxygenated only at C-8. The structure was deduced from spectral comparisons with the structurally related flavones 5,2′-, 3,2′-, and 2′,3′-dihydroxyflavone and confirmed by total synthesis. The spectral properties of other flavones oxygenation with a simple pattern are discussed in relation to 8,2′-dihydroxyflavone.

Phytochemistry published new progress about Flavonols Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Name: 2,3-Dimethoxybenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gevorgyan, Ashot published the artcileFormal C-H Carboxylation of Unactivated Arenes, Product Details of C9H9NO2, the main research area is carboxyl unactivated arene preparation green chem regioselective; unactivated arene carbon dioxide carboxylation copper catalyst; carbon dioxide aryl boronate carboxylation copper catalyst; C−H activation; carbon dioxide; carboxylation; green solvent; late-stage functionalization.

A formal C-H carboxylation of unactivated arenes e.g., I using CO2 in green solvents is described. The present strategy combines a sterically controlled Ir-catalyzed C-H borylation followed by a Cu-catalyzed carboxylation of the in situ generated organoboronates. The reaction is highly regioselective for the C-H carboxylation of unactivated arenes e.g., I (1,3-disubstituted and 1,2,3-trisubstituted benzenes, 1,2- or 1,4-sym. substituted benzenes, fluorinated benzenes and different heterocycles). The developed methodol. was applied to the late-stage C-H carboxylation of com. drugs and ligands.

Chemistry – A European Journal published new progress about Aromatic carboxylic acids Role: SPN (Synthetic Preparation), PREP (Preparation). 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Product Details of C9H9NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Master, Hoshang E. published the artcileDesign and synthesis of low molecular weight compounds with complement inhibition activity, Recommanded Product: 2,3-Dimethoxybenzonitrile, the main research area is tetrazole derivative preparation complement inhibitor; complement inhibitor phenylacrylic acid derivative preparation.

An attempt was made to synthesize a series of noncytotoxic low mol. weight compounds of varying substitutions and functionalities having pharmacophore activity like carbonyl compounds, carboxylic acid and bioisosteres like tetrazole and Ph acrylic acid. The in vitro assay of these analogs for the inhibition of complement activity revealed significant inhibitory activity for varying substituents and, particularly, for bioisosteres, i.e., tetrazole and Ph acrylic acid derivatives

Bioorganic & Medicinal Chemistry published new progress about Structure-activity relationship (complement-inhibiting). 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Recommanded Product: 2,3-Dimethoxybenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Moore, Jared T. published the artcileCatalytic alkene cyclization reactions for the stereoselective synthesis of complex “”terpenoid-like”” heterocycles, Formula: C9H9NO2, the main research area is terpenoid like heterocyclic compound preparation stereoselective synthesis.

A new catalytic synthesis of densely substituted tetrahydroquinoline derivatives is described. This reaction forms up to two rings, three bonds and three stereogenic centers with excellent stereocontrol and regiocontrol in a single step. Although control experiments demonstrate that the active catalyst is protic acid, Sc(OTf)3 serves as an effective and practical pre-catalyst. The scope of this reaction is demonstrated with cyclization reactions and bicyclization reactions. The synthesis of the target compounds (terpenoid derivatives) was achieved using geraniol derivatives as intermediates. The title compounds thus formed included a quinoline thioether derivative (I) and an isoquinoline derivative (II) and related substances, such as selenium ether derivatives

Chemical Science published new progress about Bicyclic compounds Role: SPN (Synthetic Preparation), PREP (Preparation). 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Formula: C9H9NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Yuxiao published the artcileRuthenium Trichloride Catalyzed Highly Efficient Deoximation of Oximes to the Carbonyl Compounds and Nitriles without Acceptors, Application In Synthesis of 5653-62-3, the main research area is ketone preparation green chem; ketoxime deoximation ruthenium trichloride catalyst; nitrile preparation green chem; aldoxime deoximation ruthenium trichloride catalyst.

The acceptor-free catalysis protocol for the deoximation of ketoximes e.g., I and aldoximes RCH:NOH (R = C6H5, 2,3-(H3CO)2C6H3, 4-H3CC6H4, 2-HOC6H4) using RuCl3 as the catalyst has been developed. Under the optimized conditions, various oximes were converted to ketones e.g., II and nitriles RCN with excellent isolated yields.

Chinese Journal of Chemistry published new progress about Aromatic nitriles Role: SPN (Synthetic Preparation), PREP (Preparation). 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Application In Synthesis of 5653-62-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ushijima, Sousuke published the artcileOne-pot conversion of aromatic bromides and aromatics into aromatic nitriles, Synthetic Route of 5653-62-3, the main research area is aryl bromide cyanation sequential lithiation DMF addition; arene cyanation sequential lithiation DMF addition; aromatic nitrile green preparation.

Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by sequential treatment with BuLi and DMF, followed by treatment with I2 in aqueous NH3. The same treatment of typical aromatics and heteroaromatics also provided the corresponding aromatic nitriles in good yields. The present reactions are novel 1-pot methods for the preparation of aromatic nitriles from aromatic bromides and aromatics, resp., through the formation of aryllithiums and their DMF adducts.

Synlett published new progress about Aromatic nitriles Role: SPN (Synthetic Preparation), PREP (Preparation). 5653-62-3 belongs to class nitriles-buliding-blocks, name is 2,3-Dimethoxybenzonitrile, and the molecular formula is C9H9NO2, Synthetic Route of 5653-62-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 5653-62-3, name is 2,3-Dimethoxybenzonitrile, molecular formula is C9H9NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 2,3-Dimethoxybenzonitrile

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (20 g) in dry ether (150 mL) was added 2.4M n-butyllithium in hexane (5 mL). After 10 min at room temperature, 2,3-Dimethoxybenzonitrile (16.3 g) was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was the poured onto excess 3N HCl. The aqueous layer was separated, basified with 50% NaOH and the product was exuacted three times with 10% methanol in methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvents removed in vacuo to afford 2,3-Dimethoxy-benzamidine as a glassy solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5653-62-3, its application will become more common.

Reference:
Patent; Neurogen Corporation; US5681956; (1997); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 5653-62-3, name is 2,3-Dimethoxybenzonitrile, molecular formula is C9H9NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 2,3-Dimethoxybenzonitrile

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (20 g) in dry ether (150 mL) was added 2.4M n-butyllithium in hexane (5 mL). After 10 min at room temperature, 2,3-Dimethoxybenzonitrile (16.3 g) was added in one portion and the mixture was kept at room temperature for 16 h. The reaction mixture was the poured onto excess 3N HCl. The aqueous layer was separated, basified with 50% NaOH and the product was exuacted three times with 10% methanol in methylene chloride. The combined organic extracts were dried over magnesium sulfate and the solvents removed in vacuo to afford 2,3-Dimethoxy-benzamidine as a glassy solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5653-62-3, its application will become more common.

Reference:
Patent; Neurogen Corporation; US5681956; (1997); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 5653-62-3, The chemical industry reduces the impact on the environment during synthesis 5653-62-3, name is 2,3-Dimethoxybenzonitrile, I believe this compound will play a more active role in future production and life.

Preparation of 2, 3-dihydroxy benzoic acid form 2, 3-dimethoxy benzoic acid To a stirred solution of 2, 3-dimethoxy benzoic acid (lOOg; 0.549 mol) in dichloromethane (500 mL) and catalytic amount of DMF (~2 mL) at a temperature about 30-35C, thionyl chloride (130.6g ; 1.102 mol) was added and stirred for a period of two hours. Reaction was monitored by TLC for completion of the starting material (NMT- 5%).If reaction not completed added thionyl chloride (9.8 g; 0.823 mol). Upon completion of reaction, the reaction mass was quenched in to the -5C chilled aqueous ammonia (580 mL) solution at a temperature below 15C under stirring. The reaction mass was stirred at temperature 30-35C over a period of 30 min. The separated organic fraction was concentrated under atmospheric distillation at below 50C, charged toluene (100 ml) and co-distilled until the reaction mass moisture content become less than 0.5 %. The obtained benzamide compound was dissolved in toluene (500 mL) at temperature about 30-35C.To the reaction mass was added POCl3 (126.3 g; 0.824 mol).The temperature of the reaction mass was raised to 80-85C and maintained over a period of 1 -2 hours for the completion of the reaction (Progress of the reaction was monitored by HPLC until the benzamide NMT 1.0 %). If the reaction was not completed, added second lot of POCl3 (lO.lg; 0.06 mol) at 30-35C. The reaction mass was cooled to a temperature about 30-35C upon completion of the reaction. The reaction mixture was added to cold water (1000 mL) at 0-5C.The organic fraction was separated and washed with 8% sodium bicarbonate solution. The organic fraction was separated and azeotropic distilled at 110-115C (until moisture content NMT 0.2 %), after reaching moisture content to normal limit cooled the reaction mass temperature to 40C and distilled reaction mass volume becomes ~3 volumes under vacuum at a temperature 40-50C.After distillation cooled the reaction mass temperature to 30-35C. In another RB flask charged toluene (160 ml), triethyl amine (199.7 g; 1.977 mol) at 30-35C and stirred for 10 min. charged aluminum chloride (52.7 g 5; 1.977 mol) in five lots with the gap of 10 min between each lot addition (addition of aluminum chloride may raise the temperature to 45-50C). The reaction mass temperature was raised to about 70-75 C and added above reaction mass (methoxy compound) for 30 min. maintained the reaction mass at 70-75C for 8 hr. Progress of the reaction was monitored by HPLC (until the 2,3-dimethoxybenzonitrile content 0.25 % and 3-methoxy-2-hydroxybenzonitrile content 0.2 %). If reaction was not completed added second lot of triethyl amine (27.7 g; 0.27 mol) and aluminum chloride (36.6 g; 0.27 mol).Upon completion of the reaction, the reaction mixture was cooled to 30-35C and quenched with chilled aqueous HC1 (prepared by addition of water (500 ml) and Cone. HC1 (500 ml)) at 15C. Stirred reaction mass at 25-30C for about 30 min, filtered the obtained solids and separated aqueous and organic layers. Charged MIBK (320 ml) to the solids and charged above aqueous layer, filtered through celite and separated aqueous and organic layers. To the aqueous layer given MIBK (320+160 ml) extractions. To the combined organic layer given 20% sodium chloride solution washing, organic layer was azeotropic distilled at 110C to remove the water (moisture content NMT 0.2 %).Cooled the reaction mass temperature to 30C and filtered through 0.45 micron / 1 micron filter. To the filterate charged 1% EDTA (400 ml), stirred for 30 min and filtered through 10 micron cloth. The organic fraction was separated and distilled off to obtain the residue. The residue was treated with dichloromethane (400 ml) and the solid obtained was filtered and dried under vacuum over 6 hr at 60-65C to obtain the title compound 2, 3-dihydroxy benzonitrile. (56g, yield 75.4%) Purity by HPLC 99.81 %; Impurity A: 0.05% Impurity B: 0.07 %

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,3-Dimethoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; MUDDULURU, Hari Krishna; MADHAVARAM, Shankar; WO2014/13512; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

5653-62-3, name is 2,3-Dimethoxybenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 2,3-Dimethoxybenzonitrile

2,3-Dimethoxybenzonitrile (2.0 g, 12.3 mmol), ZnBr2 (2.8 g, 12.3 mmol), and sodium azide (0.88 g, 13.5 mmol) were suspended in H2O (25 mL) and iPrOH (3 mL) and heated behind a blast shield at reflux for 24 hours. The mixture was allowed to cool to ambient temperature and diluted with EtOAc and 2N HCl. The aqueous phase was back extracted with EtOAc and the combined organic phases were dried over Na2SO4, filtered through a 1/4″ silica gel plug, and the filtrate was concentrated under reduced pressure. The residue was purified by trituration with diethyl ether to provide the title compound. MS (DClTNH3) m/z 207 (MH-H)+, m/z 181 (M+NH4-HN3)+.

The synthetic route of 5653-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2006/86229; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts