Category: 65515-39-1

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, the common compound, a new synthetic route is introduced below. COA of Formula: C9H10N2O

The 2-methoxy-4,6-dimethylnicotinic acid required as first starting material is obtained as follows: 97 g (0.6 mole) of 2-methoxy-4,6-dimethylnicotinonitrile and 230 g of solid potassium hydroxide are dissolved in 1000 ml of ethanol and 120 ml of water and the solution is refluxed under nitrogen for 82 hours. The mixture is cooled, the precipitated substance collected by filtration, and the bulk of the ethanol is distilled off from the filtrate in vacuo. The residue is dissolved in 500 ml of water and extracted with methylene chloride. The alkaline aqueous phase is adjusted to pH 3.3 with concentrated hydrochloric acid and the precipitated crude product is collected by filtration. Recrystallisation of this crude product from ethanol yields pure 2-methoxy-4,6-dimethylnicotinic acid (m.p. 210-215 C).

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4089960; (1978); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65515-39-1 , The common heterocyclic compound, 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, its 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.

2-methoxy-4,6-dimethyl-nicotinonitrile (1.0 g, 6.166 mmol) was disolved in 30 mL of anhydrous methylene chloride and then added with 6 mL of trifluoro acetic acid and N-iodosuccinimide (2.2 g, 9.248 mmol) in this order while stirring at 0 C under the nitrogen atmosphere and then stirred again at room temperature for about 4 hours. The mixture was added with 60 mL of a saturated solution of sodium carbonate and 60 mL of a saturated solution of Na2S203 and then extracted twice with 80 mL of methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, and filtered. A silica gel column chromatography (5% EtOAc/Hexanes) was performed on the resulting residue and 1.67 g (94%) of 5-iodo- 2-methoxy-4,6-dimethyl-nicotinonitrile was obtained in white solid. 1H NMR (300 MHz, CDC13) 5 2.64 (s, 3H), 2.75 (s, 3H), 4.01 (s, 3H).

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK CHEMICALS, CO., LTD.; WO2005/63768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 65515-39-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(a) 4-(but-3-en-l-yl)-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (1.5 g, 9.25 mmol) in THF (40 mL) was added LiHMDS (10.17 mL, 10.17 mmol) at -78 C, and the mixture was stirred at -78 C for 1 h. 3-Bromoprop-l-ene (0.880 mL, 10.17 mmol) was added and the mixture was stirred at -78 C for 1 h and warmed to 0 C over 1 h. The mixture was then stirred at 0 C for 3 h. The reaction was quenched with saturated aqueous H4C1 solution and extracted with EtOAc (3x). The combined organics were dried over Na2SC”4 and concentrated. The residue was purified using reverse phase HPLC using Trilution software, with a phenomenex Gemini 5u CI 8(2) 100 A, AXIA 30×100 mm 5 micron, 10- minute run (30 mL/min, 40% CH3CN/H20, 0.1% formic acid to 80% CH3CN/H20, 0.1% formic acid) with UV detection at 254 nm to afford 4-(but-3-en-l-yl)-2-methoxy-6- methylnicotinonitrile (1.01 g, 54%) as a pale yellow oil. LC-MS(ES) m/z = 203 [M+H]+.

According to the analysis of related databases, 65515-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 2-Methoxy-4,6-dimethylnicotinonitrile

To a cooled (ice water bath) solution of 2-methoxy-4,6-dimethylnicotinonitrile (10 g, 61.7 mmol) in Et2O (200 mL) was added dropwise 1 M LiAIH4 in Et2O (123 mL, 123 mmol). The ice bath was removed and the reaction mixture was stirred at r.t. for 16 h. The reaction mixture was cooled in an ice water bath and quenched with a mininum amount of water (until no more hydrogen was generated). The reaction was filtered and the insoluble material was washed with 10: 1 DCM/MeOH. The combined organic filtrates were concentrated. The residue was purified via column chromatography (0 – 30% MeOH/DCM; 100 g-HP- silica gel column) to give (2-methoxy-4,6-dimethylpyridin-3- yl)methanamine (8.9 g) as a yellowish semi-solid.

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BRACKLEY, III, James A.; GRAVES, III, Alan Peterson; KNIGHT, Steven David; MCNULTY, Kenneth C.; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (114 pag.)WO2017/2064; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 2-Methoxy-4,6-dimethylnicotinonitrile

To a cooled (ice water bath) solution of 2-methoxy-4,6-dimethylnicotinonitrile (10 g, 61.7 mmol) in Et2O (200 mL) was added dropwise 1 M LiAIH4 in Et2O (123 mL, 123 mmol). The ice bath was removed and the reaction mixture was stirred at r.t. for 16 h. The reaction mixture was cooled in an ice water bath and quenched with a mininum amount of water (until no more hydrogen was generated). The reaction was filtered and the insoluble material was washed with 10: 1 DCM/MeOH. The combined organic filtrates were concentrated. The residue was purified via column chromatography (0 – 30% MeOH/DCM; 100 g-HP- silica gel column) to give (2-methoxy-4,6-dimethylpyridin-3- yl)methanamine (8.9 g) as a yellowish semi-solid.

The synthetic route of 65515-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; BRACKLEY, III, James A.; GRAVES, III, Alan Peterson; KNIGHT, Steven David; MCNULTY, Kenneth C.; NEWLANDER, Kenneth Allen; TIAN, Xinrong; (114 pag.)WO2017/2064; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, molecular weight is 162.19, as common compound, the synthetic route is as follows.

(a) 4-ethyl-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (3.5 g, 21.58 mmol) in THF (100 mL) was added LHMDS (1M in THF) (22.66 mL, 22.66 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction was stirred at this temperature for 1 h. lodomethane (2.418 mL, 22.66 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride (60 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2x). The combined organics were dried over Na2S04, filtered, concentrated, and purified by flash chromatography (0-5% EtOAc in hexanes, 80 g column; re-columned using 0-5% EtOAc in hexanes, 80 g column) to afford 4-ethyl-2-methoxy-6-methylnicotinonitrile (2.01 g, 90% purity) as a white crystalline solid. LC-MS(ES) m/z = 176.9 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 65515-39-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile, molecular formula is C9H10N2O, molecular weight is 162.19, as common compound, the synthetic route is as follows.

(a) 4-ethyl-2-methoxy-6-methylnicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (3.5 g, 21.58 mmol) in THF (100 mL) was added LHMDS (1M in THF) (22.66 mL, 22.66 mmol) at 0 C dropwise via dropping funnel over 10 min, and the reaction was stirred at this temperature for 1 h. lodomethane (2.418 mL, 22.66 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride (60 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2x). The combined organics were dried over Na2S04, filtered, concentrated, and purified by flash chromatography (0-5% EtOAc in hexanes, 80 g column; re-columned using 0-5% EtOAc in hexanes, 80 g column) to afford 4-ethyl-2-methoxy-6-methylnicotinonitrile (2.01 g, 90% purity) as a white crystalline solid. LC-MS(ES) m/z = 176.9 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 65515-39-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65515-39-1, 2-Methoxy-4,6-dimethylnicotinonitrile, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, COA of Formula: C9H10N2O, blongs to pyridine-derivatives compound. COA of Formula: C9H10N2O

Example 8: (2-Methoxy-4,6-dimethylpyridin-3-yl)methanamine To a slurry solution of aluminum (III) lithium hydride (234 mg, 6.17 mmol) in diethyl ether (2 ml_) was added a saturated solution of 2-methoxy-4,6- dimethylnicotinonitrile (500 mg, 3.08 mmol) in ether (5 ml_) and stirred at room temperature for 1 h. After completion of the reaction, minimum amount of water was carefully added and the crude product obtained was extracted with hot benzene / toluene and concentrated. Resulting oily compound was distilled at 0.5 mm vacuum at 95-100 SC to obtain the title compound. Yield: 300 mg (58.66 %); 1H NMR (DMSO-d6, 300 MHz): delta 6.53 (s, 1 H), 3.92 (s, 3H), 3.76 (s, 2H), 2.36 (s, 3H), 2.27 (s, 3H); MS (ESI+): m/z 166.9 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,65515-39-1, 2-Methoxy-4,6-dimethylnicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; SHARMA, Rajiv; GUPTE, Amol; ROYCHOWDHURY, Abhijit; JADHAV, Ravindra, Dnyandev; KANDRE, Shivaji, Sadashiv; KADAM, Kishorkumar, Shivajirao; CHAVAN, Sambhaji; GADEKAR, Pradip, Keshavrao; GUHA, Tandra; WO2014/155301; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem