Category: 76469-88-0

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

To a solution of methyl 4-(cyanomethyl)benzoate (9.5 g, 54.2 mmol) in ethanol (100 mL), hydroxylamine hydrochloride (6.78 g, 98 mmol) and sodium bicarbonate (8.20 g, 98 mmol) were added. The resulting reaction mixture was stirred at 65 oC for 18 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to obtain methyl-4-(2-amino-2- (hydroxyimino)ethyl)benzoate (11.2 g, 53.8 mmol, 99 % yield).

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

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. Application In Synthesis of Methyl 4-(cyanomethyl)benzoate

Step 2: 2-(4-(Methoxycarbonyl)phenyl)acetic Acid A stirred solution of methyl 4-(cyanomethyl)benzoate (22.0 g, 0.125 mol) in methanol (550 mL) was bubbled through with hydrogen chloride gas for 8 h under reflux conditions. The reaction mixture was cooled to 20 C., stirred for an additional 24 h and filtered. The filtrate was evaporated under reduced pressure. The resultant residue was dissolved in diethyl ether, washed sequentially with water and saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and evaporated to afford the methyl ester as a solid residue. 1H NMR (400 MHz, CDCl3): 8.00 (d, J=8 Hz, 2H); 7.35 (d, J=8.4 Hz, 2H); 3.91 (s 3H); 3.70 (s, 3H); 3.68 (s, 2H). GCMS: 209 (M+H). The methyl ester (8.21 g, 0.039 mmol) was dissolved in methanol, treated with sodium hydroxide (1.58 g, 0.039 mol), heated to 50 C., stirred for 4 h, cooled to room temperature, stirred for an additional 24 h and concentrated in vacuo. The resultant residue was partitioned between diethyl ether and water. The aqueous layer was acidified with concentrated HCl. The resultant precipitate was removed by filtration and dried overnight, under vacuum, to afford 2-(4-(methoxycarbonyl)phenyl)-acetic acid (80%) as an off-white solid. 1H NMR (400 MHz, DSMO-d6): 7.90 (d, J=8 Hz, 2H); 7.422 (d, J=8 Hz, 2H); 3.85 (s 3H) 3.68 (s, 2H). [M+H] 195

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

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., Computed Properties of C10H9NO2

PREPARATION 13 4-(cyanomethyl)benzoic acid To a stirred solution of methyl 4-(cyanomethyl)benzoate (10 g, 60 mmol) in THF (500 ml) a solution of LiOH (2.90 g, 70 mmol) in water (600 ml) was added. It was stirred at room temperature for 16h. The mixture was concentrated in vacuo and onto the aqueous phase left a solution of HCl 35% (6ml) was added. The solid obtained was filtered, washed with water and hexane and dried in vacuo at 40C for 64h. It was treated with hexane (100 ml) stirring for 1 h. The solid obtained was filtered and dried to yield 7.95 g (86%) of the title compound. LRMS: m/z 260 (M-1)- Retention time: 2.10 min (method A)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Almirall, S.A.; EP2343287; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 76469-88-0, 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.

Step 1 : A solution of A/fA/-diisopropylethytamine (2.4 mL, 17.1 mmol, 1 eq) in THF (10 mL) was cooled to -78C. A solution of /7-butyllithium in hexanes (2.5M, 6.85 mL, 17.1 eq) was added dropwise with stirring. The solution was warmed to 0C for 10 min, then cooled again to -78C. At -78C, a solution of methyl 4-(cyanomethyl)benzoate (3g, 20 mmol, 1 eq) in THF (8 mL) was added dropwise to the LDA solution (a dark red slurry formed). After stirring the resulting slurry for 10 minutes at -78C, 1-bromo-3,3- dimethylbutane (2.46 mL, 17.9 mmol, 1.05 eq) was added rapidly. The reaction was stirred for 30 minutes at -78C then was warmed to room temperature. After 1h, hexamethylphosphoramide (2.5 mL, 14 mmol) was added, and the reaction was stirred at room temperature for 16h. The reaction mixture was partitioned between EtOAc and 1N HCi. The aqueous layer was discarded, and the organic layer was washed with 1 HCI and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which waschromatographed on silica gel (gradient elution, 0% to 30% EtOAc in hexanes, SiO2) to afford the desired product as a white crystalline solid (2.49g, 54%),

The synthetic route of Methyl 4-(cyanomethyl)benzoate 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

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

Methyl 4-(cyanomethyl)benzoate (25g, 0.14mol) dissolved in 300mL methanol was add 160mL 1N NaOH and refluxed for3 hours. Most of the solvent was removed in vacuo. The residue was added 500mL water and acidified to pH 2-3 with concentrated HCl. The generated solid was filtered, washed with water and dried to give the title compound as white solid (21.2g, 92.2%): 1H NMR (400MHz, DMSO-d6) delta 12.89 (brs, 1H), 7.87 (d, J=8.2Hz, 2H), 7.37 (d, J=8.2Hz, 2H), 3.45 (s, 2H); MS(EI): 161[M]+.

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

Reference:
Article; Chen, Danqi; Shen, Aijun; Li, Jian; Shi, Feng; Chen, Wuyan; Ren, Jing; Liu, Hongchun; Xu, Yechun; Wang, Xin; Yang, Xinying; Sun, Yiming; Yang, Min; He, Jianhua; Wang, Yueqin; Zhang, Liping; Huang, Min; Geng, Meiyu; Xiong, Bing; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 87; (2014); p. 765 – 781;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts