Category: 18469-52-8

Application of 18469-52-8,Some common heterocyclic compound, 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, molecular formula is C9H11NO2, 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.

General procedure: To a solution of 2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid (1.0 equiv) in DMF was added HOBT (1.2 equiv) and EDCI (1.2 equiv), and the mixture was stirred for thirty minutes at room temperature. Triethylamine and corresponding 5a-5e was added, and then reaction was stirred for 8 h at room temperature. Then it was quenched by H2O. The mixture was washed with brine and extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by chromatography on a silica gel chromatography (petroleum ether/ethyl acetate = 1:1 to 1:20) to give corresponding products 6a-6e (yield 43%-62%) as white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-(aminomethyl)benzoate, its application will become more common.

Reference:
Article; Liao, Chenzhong; Tian, Yongbin; Xie, Zhouling; Bioorganic and medicinal chemistry letters; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, belongs to esters-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 18469-52-8, SDS of cas: 18469-52-8

(1) To a solution of methyl 4-(aminomethyl)benzoate (5.08 g) in methylene chloride (30 mL) was added di-tert-butyl dicarbonate (6.4 g) under ice-cooling and the mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with methylene chloride (20 mL) and thereto was added water (40 mL). After stirring, the organic layer was separated and concentrated in vacuo to give crude methyl 4-[N-(tert-butoxycarbonyl)aminomethyl] benzoate.

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; TANABE SEIYAKU CO., LTD.; EP1772454; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, belongs to esters-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 18469-52-8, Recommanded Product: 18469-52-8

General procedure: To a solution of acid 3 (1.25 g, 3.1 mmol), HBTU (1.6 g, 3.7 mmol),and Et3N (10 mL) in 20 mL acetonitrile was added 1.2 equimolaramount of the appropriate amine. The mixture was kept stirring atroom temperature for 5 h. TLC detection found that the reactionwas complete, then the mixture was evaporated under reducedpressure to remove solvent. The residue was taken up saturatedsodium chloride and 1mL 3 N HCl and extracted with ethyl acetate(30 mL x 3), and the combined organic layers were washed twotimes with saturated sodium chloride and 1mL 3 N HCl. Theorganic layers were dried (MgSO4), filtered, and solvent wasremoved under reduced pressure at 40 C to give the crude product,which was purified by column chromatography to produce thecorresponding intermediate, 4 and 7.

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

Reference:
Article; Jia, Ruifang; Zhang, Jian; Ai, Wei; Ding, Xiao; Desta, Samuel; Sun, Lin; Sun, Zhuosen; Ma, Xiuli; Li, Zhong; Wang, Defeng; Huang, Bing; Zhan, Peng; Liu, Xinyong; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 64 – 80;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 18469-52-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

Commercially available methyl bromomethylbenzoate (manufactured by Aldrich Corporation) (10.0 g) was dissolved in DMF (100 ml), and the solution was added with potassium phthalimide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (9.70 g) and the whole was stirred at room temperature for 1.5 hours. After completion of the reaction, the solution was concentrated and added with water, followed by extraction with chloroform. The resultant was washed with a saturated saline solution and dried with anhydrous sodium sulfate, and the solvent was distilled off, thereby obtaining a white solid (12.9 g). Subsequently, 7.56 g of the solid was dissolved in methanol (100 ml), and the solution was added with hydrazine monohydrate (manufactured by Nacalai Tesque, Inc.) (6.25 ml) and the whole was stirred at 60C for 1.5 hours. After completion of the reaction, the precipitated solid was filtrated out and the solvent was distilled off. The resultant was added with water and subjected to extraction with chloroform. The resultant was washed with a 0.3 mol/l sodium hydroxide aqueous solution and a saturated saline solution and dried with anhydrous sodium sulfate, and the solvent was distilled off. Methanol (120 ml) and 2-imidazole carboxaldehyde (manufactured by Aldrich Corporation) (2.35 g) were added to the resultant and the whole was stirred at room temperature for 2 days. After completion of the reaction, the precipitated solid was filtrated out. The liquid layer was concentrated and evaporated to dryness, and washing was performed by adding anhydrous methanol (30 ml). Then, the solid was filtrated out. The resultant solid and the solid that had been previously filtrated out were suspended in methanol (86 ml), and sodium borohydride (1.42 g) was added under ice-cooling. The solution was stirred at room temperature for 1 hour, and the solvent was distilled off. After addition of water, extraction was performed with chloroform, and the organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure and drying, thereby obtaining a colorless oily substance (4.32 g). 4.28 g of the oily substance was dissolved in DMF (65 ml), and the solution was added with di-t-butyldicarbonate (8.90 ml) and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off, and the residue was dissolved in chloroform, followed by washing with a saturated saline solution. After drying with anhydrous sodium sulfate, the solvent was distilled off, and THF (43 ml), methanol (43 ml), and a 1 mol/l sodium hydroxide aqueous solution (43 ml) were added to the resultant, followed by stirring at room temperature for 14 hours. After completion of the reaction, the solvent was distilled off, and water (5.0 ml) was added to the resultant. Further, 1 mol/l hydrochloric acid was carefully added to the solution, and the acid-precipitate was filtrated out and dried, thereby obtaining the subject compound (4.87 g) as a white solid. MS(FAB,Pos.):m/z=332[M+H]+

The chemical industry reduces the impact on the environment during synthesis Methyl 4-(aminomethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18469-52-8, name is Methyl 4-(aminomethyl)benzoate, belongs to esters-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-(aminomethyl)benzoate

Step 4. A solution of 5-fluoro-1H-indazole-3-carboxylic acid (0.25 g, 0.74 mmol) in dichloromethane (5.0 mL) was treated with triethylamine (0.083 g, 0.11 mL, 0.82 mmol), 4-dimethylamino pyridine (0.14 g, 1.1 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.17 g, 0.89 mmol). 4-Aminomethyl-benzoic acid methyl ester (0.16 g, 0.82 mmol) was added. The mixture was stirred at room temperature for 16 hours, then partitioned between diethyl ether and 1N HCl. The organic phase was washed with water and brine, dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), to yield 4-({[1-(4-difluoromethoxy-benzyl)-5-fluoro-1H-indazole-3-carbonyl]-amino}-methyl)-benzoic acid methyl ester as a yellow solid, 0.19 g (54%), m/z (ISP): 484.5 (M+H).

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ackermann, Jean; Bleicher, Konrad; Ceccarelli, Simona M.; Chomienne, Odile; Mattei, Patrizio; US2008/103182; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics