Category: 13388-75-5

Electric Literature of 13388-75-5, A common heterocyclic compound, 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, molecular formula is C10H11NO2, 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.

Example 487 Preparation of the intermediate 5-bromo-3-(3,5- dimethoxy-phenyl)-pyrazolo[1 ,5-a]pyrimidineExample 487a Preparation of 2-(3,5-dimethoxy-phenyl)-3- dimethylamino-acrylonitrileA mixture of (3,5-dimethoxy-phenyl)-acetonitrile (19.9 g, 112 mmol), N,N,N’,N’-tetramethyl-ethane-1 ,2-diamine (2.86 mL, 19.09 mmol) and dimethyl formamide dimethyl acetal (72 mL) were heated at reflux for 4 h. On cooling, the reaction was partitioned between EtOAc and saturated aqueous ammonium chloride solution, and the mixture filtered, and the residue washed with EtOAc and dried to give 2-(3,5-dimethoxy-phenyl)-3- dimethylamino-acrylonitrile (7.1 g, 27%). The filtrates were combined, extracted and the combined organic phase washed with brine and concentrated in vacuo. The crude product was purified by chromatography on silica gel to give 2-(3,5-dimethoxy-phenyl)-3-dimethylamino-acrylonitrile (11.1 g, 43%). 1H-NMR (300 MHz, d6-DMSO): delta = 7.44 (1H, s), 6.42 (2H, d), 6.20 (1 H, t), 3.69 (6H, s), 3.15 (6H, s) ppm.

The synthetic route of 13388-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2007/147647; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

13388-75-5, Adding some certain compound to certain chemical reactions, such as: 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, 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 13388-75-5.

Under a nitrogen atmosphere, add 0.2 mmol of 3,5-dimethoxyphenylacetonitrile to a 25 mL reaction flask equipped with a reflux condenser.0.6 mmol of lithium tert-butoxide, 0.6 mmol of alpha-trifluoromethylstyrene, 4 ml of dimethyl sulfoxide, the reaction system was stirred at 80C for 12 hours,Stop heating and stirring, cool to room temperature, add water to quench the reaction, add ethyl acetate to extract the reaction solution,The ethyl acetate layer was subjected to rotary evaporation under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product,The column chromatography eluent used was a petroleum ether: ethyl acetate mixed solvent with a volume ratio of 30:1; the yield of the product was 83%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 13388-75-5.

Reference:
Patent; South China University of Technology; Zhu Chuanle; Cai Yingying; Zeng Hao; Jiang Huanfeng; (21 pag.)CN111205202; (2020); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile, 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. 13388-75-5

General procedure: A 50 mL round-bottomed flask was charged with 3 (0.177 g, 1 mmol), aromatic aldehyde or substituted aromatic aldehyde (1 mmol) and 10 mL methanol with stirring, and the mixture was heated to 60 C. After 30 min, sodium methoxide (0.027 g, 0.5 mmol) was added to the mixture and keep the temperature for 4-6 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to RT, and the precipitate was separated by filter and recrystallized from methanol to give 4a-4z and 5a-5d.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 13388-75-5.

Reference:
Article; Ma, Jun; Li, Jiajun; Tian, Yu-Shun; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 81 – 85;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts