Category: 76469-88-0

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 4-(cyanomethyl)benzoate

General procedure: To a solution of potassium tert-butoxide (8.0 g, 0.08 mmol,2.5 equiv) in THF (25 ml) at 30 C was added a solution of methyliodide (5.35 ml, 0.09 mmol, 3.0 equiv) and methyl 4-(cyanomethyl)benzoate (5.0 g, 0.03 mmol,1.0 equiv) in THF (25 ml) under nitrogen atmosphere over 20 min. The cooling bath was removed and the reaction mixture was allowed to warm to rt and stirred for 2 h.Following this the reaction was quenched with water (10 ml) and ethyl acetate was added and the organic and aqueous layers were separated. The organic layer was washed with water, brine, anddried over sodium sulfate. The organic solvent was removed under vacuum to obtain a violet residue that was purified by column chromatography using 20:80 EtOAc:Pet ether to obtain an off white solid that was crystallized in CHCl3:Pet ether to afford the title compound (4.0 g, 69%) as a white solid.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kadam, Kishorkumar S.; Jadhav, Ravindra D.; Kandre, Shivaji; Guha, Tandra; Reddy, M. Mahesh Kumar; Brahma, Manoja K.; Deshmukh, Nitin J.; Dixit, Amol; Doshi, Lalit; Srinivasan, Shaila; Devle, Jayendra; Damre, Anagha; Nemmani, Kumar V. S.; Gupte, Amol; Sharma, Rajiv; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 337 – 347;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 76469-88-0, 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. 76469-88-0 name is Methyl 4-(cyanomethyl)benzoate, This 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 100 mL flask was charged with methyl 4-(cyanomethyl)benzoate (1 g, 5.7 mmol), acetonitrile (46 mL), cesium carbonate (5.6 g, 17 mmol) and 1,2-dibromoethane (1.3 g, 5.8 mmol). The resulting suspension was stirred at 80C for three hours, cooled at room temperature and quenched with water (30 mL). The aqueous mixture was extracted with ethyl acetate (2 × 20 mL), the combined organic phases were washed with water (5 mL), brine (5 mL), dried with Na2SO4, filtered and evaporated. Purification by chromatography over silica gel (cyclohexane/ethyl acetate gradient, 1:01:1) affords methyl 4-(1-cyanocyclopropyl)benzoate. (0527) 1H-NMR (400 MHz, CDCl3): d = 8.05-8.00 (m, 2H), 7.37-7.33 (m, 2H), 3.93 (s, 3H), 1.85-1.80 (m, 2H), 1.51-1.47 (m, 2H); ); (0528) LC-MS (method 1): Rt 0.87, m/z = 202 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-(cyanomethyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien, Daniel, Henri; EDMUNDS, Andrew; EMERY, Daniel; HALL, Roger, Graham; HUETER, Ottmar, Franz; KOLLETH KRIEGER, Amandine; RENDLER, Sebastian; SCHAETZER, Juergen, Harry; (0 pag.)WO2020/2563; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, belongs to nitriles-buliding-blocks compound, 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 76469-88-0, Recommanded Product: 76469-88-0

Referential Example 57 Methyl 4-[2-(tert-butoxycarbonylamino)ethyl]benzoate Methyl 4-cyanomethylbenzoate (0.20 g) was dissolved in a mixed solvent of methanol (15 ml) and chloroform (0.4 ml). To the resulting solution, platinum dioxide (33 mg) was added, followed by catalytic reduction at room temperature under 3 atmospheric pressure for 3 hours. The catalyst was removed by filtration through Celite and the solvent was distilled off under reduced pressure. The residue was suspended in dichloromethane (5 ml), followed by the addition of triethylamine (160 mul). After the addition of a solution of di-tert-butyl dicarbonate (0.29 g) in dichloromethane (dichloromethane: 2 ml) under ice cooling, the resulting solution was stirred at room temperature for 13 hours. The reaction mixture was diluted with dichloromethane, washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate 10:1~5:1), whereby the title compound (0.28 g, 88%) was obtained. 1H-NMR (CDCl3) delta: 1.43(9H,s), 2.86(2H,t,J=6.8 Hz), 3.39(2H,m), 3.91(3H,s), 4.53(1H,br), 7.27(2H,d,J=8.3 Hz), 7.98(2H,d,J=8.3 Hz).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Daiichi Pharmaceutical Co., Ltd.; US6525042; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 76469-88-0, A common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, molecular formula is C10H9NO2, 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.

Step 1; Methyl 4-(cyanomethyl)benzoate (1.8 g, 10 mmol, 1 eq) was dissolved in THF (100 mL) and cooled to 0C. Sodium hydride (60% w/w in mineral oil, 820 mg, 20 mmol, 2 eq) was added portionwise and the mixture was stirred for 10 minutes. Methyl iodide (1.3 mL, 20 mmol, 2 eq) was added dropwise and the reaction was stirred at 0C until the starting material was consumed by TLC (2 hours). The reaction mixture was quenched with water and was partitioned between EtOAc and brine. The aqueous layer was discarded, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which was chromatographed on silica gel (gradient elution, 0% to 50% EtOAc in hexanes, Si02) to afford the desired product as a white crystalline solid (1.88g, 74%).

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, belongs to nitriles-buliding-blocks compound, 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 76469-88-0, SDS of cas: 76469-88-0

A solution of methyl 4- (cyanomethyl) benzoate 24, (2.0 g, 11.4 mmol) in 6M Sodium hydroxide (15 mi) and methanol (15 mL) was heated at 90 C. overnight. After concentrating the reaction mixture, the aqueous layer was washed with dichloromethane (30 mL chi 2), then acidified to pH~3 with 12 HC1. The aqueous solution was extracted with ethyl acetate (20 ml 2). Organics was combined, dried over Na2S< and evaporated in vacuo to give titled compound. (1.45 mg, 70%). [M+H]* = 181.4 (APCI+) . If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it. Reference:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, A new synthetic method of this compound is introduced below., Formula: C10H9NO2

General procedure: To a solution of potassium tert-butoxide (8.0 g, 0.08 mmol,2.5 equiv) in THF (25 ml) at 30 C was added a solution of methyliodide (5.35 ml, 0.09 mmol, 3.0 equiv) and methyl 4-(cyanomethyl)benzoate (5.0 g, 0.03 mmol,1.0 equiv) in THF (25 ml) under nitrogen atmosphere over 20 min. The cooling bath was removed and the reaction mixture was allowed to warm to rt and stirred for 2 h.Following this the reaction was quenched with water (10 ml) and ethyl acetate was added and the organic and aqueous layers were separated. The organic layer was washed with water, brine, anddried over sodium sulfate. The organic solvent was removed under vacuum to obtain a violet residue that was purified by column chromatography using 20:80 EtOAc:Pet ether to obtain an off white solid that was crystallized in CHCl3:Pet ether to afford the title compound (4.0 g, 69%) as a white solid.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kadam, Kishorkumar S.; Jadhav, Ravindra D.; Kandre, Shivaji; Guha, Tandra; Reddy, M. Mahesh Kumar; Brahma, Manoja K.; Deshmukh, Nitin J.; Dixit, Amol; Doshi, Lalit; Srinivasan, Shaila; Devle, Jayendra; Damre, Anagha; Nemmani, Kumar V. S.; Gupte, Amol; Sharma, Rajiv; European Journal of Medicinal Chemistry; vol. 65; (2013); p. 337 – 347;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 4-(cyanomethyl)benzoate

Step 2: Synthesis of (Z)-methyl 4-(2-(6-chloro-1-(4-fluorobenzyl)-1H-indazol-3-yl)-1-cyanovinyl)benzoateThe product from step 1 (30.8mg, 0.106mmol), methyl 4-(cyanomethyl)benzoate (18.7mg, 0.106mmol), NaOH (4.3mg, 0.106mmol) were dissolved in MeOH (l . lmL) at room temperature then heated to 50C for 20 minutes. The mixture was then cooled, filtered and dried to give a solid (49mg).

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAKEA, INC.; HUTCHINSON, John, Howard; PARR, Timothy, Andrew; BUNKER, Kevin, Duane; LONERGAN, David; WO2015/42052; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 76469-88-0, 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. 76469-88-0 name is Methyl 4-(cyanomethyl)benzoate, This 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 100 mL flask was charged with methyl 4-(cyanomethyl)benzoate (1 g, 5.7 mmol), acetonitrile (46 mL), cesium carbonate (5.6 g, 17 mmol) and 1,2-dibromoethane (1.3 g, 5.8 mmol). The resulting suspension was stirred at 80C for three hours, cooled at room temperature and quenched with water (30 mL). The aqueous mixture was extracted with ethyl acetate (2 × 20 mL), the combined organic phases were washed with water (5 mL), brine (5 mL), dried with Na2SO4, filtered and evaporated. Purification by chromatography over silica gel (cyclohexane/ethyl acetate gradient, 1:01:1) affords methyl 4-(1-cyanocyclopropyl)benzoate. (0527) 1H-NMR (400 MHz, CDCl3): d = 8.05-8.00 (m, 2H), 7.37-7.33 (m, 2H), 3.93 (s, 3H), 1.85-1.80 (m, 2H), 1.51-1.47 (m, 2H); ); (0528) LC-MS (method 1): Rt 0.87, m/z = 202 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-(cyanomethyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; GAGNEPAIN, Julien, Daniel, Henri; EDMUNDS, Andrew; EMERY, Daniel; HALL, Roger, Graham; HUETER, Ottmar, Franz; KOLLETH KRIEGER, Amandine; RENDLER, Sebastian; SCHAETZER, Juergen, Harry; (0 pag.)WO2020/2563; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, 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. name: Methyl 4-(cyanomethyl)benzoate

j00372j To a solution of product from Step 2 (200 mg, 0.695 mmol) in methanol (30 mL) were added methyl 4-(cyanomethyl)benzoate (0.83 4 mmol) and NaOH (1.39 mmol). The resulting mixture was stirred at 50C for 4h. After the reaction mixture was cooled, it was diluted with THF (20 mL) then stirred at room temperature for 10 minutes. The solids were isolated by filtration to provide the title compound (202 mg, 65%) as a yellow solid. LCMS [M+H]: 444.9.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Electric Literature of 76469-88-0, A common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, molecular formula is C10H9NO2, 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.

A solution of methyl iodide (5.35ml) and methyl 4-(cyanomethyl)benzoate (5g) in THF (25ml) was added slowly to a solution of potassium tert-butoxide (8 g) in THF (25ml) at -30 C in an inert atmosphere. The reaction mixture was stirred at RT for about 2 hours. It was then quenched with water (10 ml) and EtOAc was added. The organic and aqueous layers were separated. Organic layer was washed successively with water, brine and dried over sodium sulfate. Organic solvent was concentrated to obtain violet residue which was purified by silica gel column chromatography using 20 % EtOAc – Petroleum ether to obtain off white solid. The off white solid was crystallized in chloroform – petroleum ether to obtain title compound as white solid. *HNMR (CDC13; 300MHz): delta 8.06 (d, 2H), 7.58 (d, 2H), 3.97 (s, 3H), 1.76 (s, 6H); MS (ESI) m/z 204.1 [M+H]+.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.