Category: 38487-85-3

Fan, Zhenhua; Yang, Shanxue; Peng, Xin; Zhang, Cheng; Han, Jing; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo published the artcile< Metal-free synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade michael addition / cyclization of methyl-4,4-difluorobut-2-ynoate with 2-aminobenzonitriles>, Synthetic Route of 38487-85-3, the main research area is difluoromethylated quinoline preparation DBU michael cyclization methyl difluorobutynoate aminobenzonitrile.

A facile synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade Michael addition/cyclization between functionalized 2-aminobenzonitriles and Me 4,4-difluorobut-2-ynoate was developed. Various highly functionalized quinolines were assembled in moderate to good yields under mild metal-free reaction conditions.

Tetrahedron published new progress about Aromatic nitriles Role: RCT (Reactant), RACT (Reactant or Reagent) (2-aminobenzonitriles). 38487-85-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H8N2O, Synthetic Route of 38487-85-3.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, molecular formula is C8H8N2O, 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. category: nitriles-buliding-blocks

General procedure: In a 10-mL Schlenk tube, the mixture of 2-aminobenzonitriles 1 (1.0 mmol) and methyl 4,4-difluorobut-2-ynoate 2 (1.5 equiv.) was stirred in MeOH (2.0 mL) at 80 C for 12 h, then DBU (3.0 equiv.) was added and continued to be stirred at 80 C for another 1 h. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (petroleum ether / ethyl acetate or dichloromethane 10:1 to 1:1 as the eluent) on silica gel to give the desired 2-difluoromethylated quinolines 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 38487-85-3, its application will become more common.

Reference:
Article; Fan, Zhenhua; Yang, Shanxue; Peng, Xin; Zhang, Cheng; Han, Jing; Chen, Jie; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo; Tetrahedron; vol. 75; 7; (2019); p. 868 – 873;,
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. 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 2-Amino-4-methoxybenzonitrile

To a stirred solution of 2-amino-4-methoxy benzonitrile (19.4 g, 131 mmol) in acetonitrile (582 mL) was added NBS (18.66 g, 104 mmol) and the mixture was stirred for 1 h at 0 C. The reaction was quenched by addition of ice. The volatiles were concentrated under reduced pressure and the residue was extracted with ethylacetate (2 x 200 mL). The combined organic layers were washed with brine solution (200 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 2-amino-5-bromo-4-methoxy benzonitrile (26 g, 114 mmol, 87% yield) as a brown solid. LCMS (ESI) m/e 227.6 (bromo pattern) [(M+H), calcd for C8H8BrN2O, 227.06]; LC/MS retention time (method C): ti = 1.46 mm.

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; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, 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 38487-85-3, Formula: C8H8N2O

EXAMPLE 28 9-Amino-3,4-dihydro-6-methoxyacridin-1(2H)-one 2-Amino-4-methoxybenzonitrile (7.51 g) was suspended in 75 ml of benzene containing 6.&sl0; g of cyclohexane-1,3-dione and 1.1 g of p -toluenesulfonic acid monohydrate. The reaction mixture was brought to reflux, at which time a homogeneous solution was obtained. After 15 minutes a thick precipitate developed, which was stirred in the refluxing solvent for an additional 15 minutes. At the end of this time thin layer chromatography (TLC, hereafter) showed that the starting material had been consumed, so the precipitate was filtered off, taken up in 2-butanone, and washed with sodium bicarbonate solution. The organic phase was dried and evaporated to a solid, which was triturated with ether to give 1&sl0;.61 g of the enamine, mp 194-196C. This material was suspended in 25&sl0; ml of tetrahydrofuran to which was then added 11.9 g of milled potassium carbonate and &sl0;.85 g of CuCl. The reaction mixture was then refluxed for a total of 48 hours, with additional portions of CuCl (&sl0;.5&sl0; g at a time) added at 6 hour and at 3&sl0; hour. At the end of this time methanol (1&sl0;&sl0; ml) was added to the reaction mixture and reflux was continued for 15 minutes. It was then filtered through diatomaceous earth, evaporated, and purified by flash chromatography (1&sl0;% methanol-dichloromethane). Obtained in this manner was 5.1 g of product that was suitable to be carried on to the next step. A 1.5 g portion was recrystallized from methanol to give 1.12 g of analytically pure material, mp 244-246C.

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Reference:
Patent; HOECHST-ROUSSEL, PHARMACEUTICALS INCORPORATED; EP179383; (1991); B1;,
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. 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 38487-85-3

General procedure: To the solution of anthranilonitrile S-1 (2.0 mmol) and Et3N (2.4 mmol) in 20 mL dry CH2Cl2 was added acryloyl chloride (2.2 mmol) at 0 C. The mixture was allowed to stir at room temperature. After completion of the reaction, the reaction was quenched with saturated NaHCO3 solution, then extracted with CH2Cl2, washed with brine, dried over MgSO4 and concentrated by evaporator affording amide S-2 without any further purification.

The synthetic route of 38487-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Tao; Zhou, Jia-Li; Li, Junpeng; Shen, Yuehai; Gao, Chuanzhu; Li, Ya-Min; Synthesis; vol. 50; 17; (2018); p. 3460 – 3466;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts