Category: 5961-59-1

Some common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, molecular formula is C8H11NO, 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. Recommanded Product: 4-Methoxy-N-methylaniline

HATU (1.5 g, 4.0 mmol) was added to a stirred solution of 4-methoxy-N-methylaniline mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.0 mmol) in DMF (20 mL) and DIPEA (1.3 mL, 7.3 mmol) and the reaction mixture was stirred at rt for 4h. The reaction was concentrated and the residual crude oil was partitioned between EtOAc (-60 mL) and 1/2 sat. NaHCC (aq) (-60 mL). The organic component was washed with brine (-40 mL), dried (MgS04), filtered, concentrated and purified using a Biotage Horizon (80 g SiC , 10-40% EtOAc/hexanes) to yield Intermediate JB-1 (1.34 g) as a clear amber viscous oil. LC-MS retention time = 3.17 min; m/z = 385.3 [M+H]+. (Column: Phenonenex-Luna C18 2.0 x 50mm 3 muiotaeta. Solvent A = 95% Water:5% Acetonitrile: 10 mM NH4OAc. Solvent B = 5% Water:95% Acetonitrile: 10 mM NH4OAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 4 min. Wavelength = 220). NMR (400 MHz, CDCh) delta 7.25 – 7.20 (m, 3H), 7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (app q, J=7.4 Hz, 1H), 3.83 (s, 3H), 3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5961-59-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
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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. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H11NO

Starting material Boc-L-phenylalanine (1) (2.90 g, 10.93 mmol, 1.5 eq.),1H-benzotriazol-1-yloxytripyrrolidinyl hexafluorophosphate (5.69 g, 10.93 mmol, 1.5 eq.) was added to 20 mL of dichloromethane and stirred for 30 min under ice bath;Then N,N-diisopropylethylamine (3.61 mL, 21.87 mmol, 3 eq.) was added.And N-methyl-4-aminoanisole (1.0 g 7.29 mmol, 1 eq.),Remove the ice bath and transfer to room temperature for stirring. TLC monitoring; after 6 hours, the reaction is completed.The solvent was distilled off under reduced pressure, and then 40 mL of saturated sodium hydrogen carbonate solution and 40 mL of dichloromethane were added to the residue, and the organic phase was separated and washed with 40 mL of 1N HCl solution.The organic phase was separated and washed with 40 mL of a saturated sodium chloride solution.The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated.The obtained crude product was separated by silica gel column chromatography (eluent EA: PE = 1:8 v/v)Getting an intermediate(S)-(1-((4-Methoxyphenyl)(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamic acid tert-butyl ester (2) crude product 2.48 g, yellow oil, yield 88%.

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 5961-59-1.

Reference:
Patent; Shandong University; Liu Xinyong; Sun Lin; Zhan Peng; Huang Tianguang; Li Guoxiong; Wu Gaoshan; (39 pag.)CN109796418; (2019); A;,
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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. 5961-59-1, name is 4-Methoxy-N-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 5961-59-1

27.4 mg (0.2 mmol) of N-methyl-4-methoxyaniline, 81.2 mg of ethyl bromodifluoroacetate (0.4 mmol), 2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent. The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated. The solvent was removed and the residue was chromatographed on silica gel. It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1. The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator. Drying in vacuo to give the yellow liquid N-(4-methoxyphenyl)-N-methylformamide 26.4 mg, yield 80%.

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou University; Zhang Xiaohong; Li Xiaofang; Zhang Xingguo; (15 pag.)CN108774147; (2018); A;,
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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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., 5961-59-1

General procedure: A 25 mL oven-dried Schlenk tube was sequentially added N-methylaniline 1 or aniline 4 (0.2 mmol), Ethyl Bromodifluoroacetate 2a (81.2 mg, 0.4 mmol), DMF (1ml) and H2O (1 mL) was added under air. The reaction mixture was stirred for 6 h at 110. The solution was then diluted with ethyl acetate (20 mL), washed with brine (10 mL), extracted with ethyl acetate (3*5 mL), dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The crude reaction mixture was purified by column chromatography (silica gel, ethyl acetate/petroleum ether) yielded the desired product 3 or 5.

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:
Article; Xu, Zhuo-Wei; Xu, Wen-Yi; Pei, Xiao-Jun; Tang, Fei; Feng, Yi-Si; Tetrahedron Letters; (2019);,
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5961-59-1, The chemical industry reduces the impact on the environment during synthesis 5961-59-1, name is 4-Methoxy-N-methylaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 2,4-Dichloropyrimidine (1) (0.149g, 1.0 mmol) in 15 mL isopropanol was added 4-methoxy-N-methylaniline derivative (2) (1.0 mmol). The reaction mixture was stirred at room temperature and monitored by TLC. When the reaction was completed, the solvent was removed under vacuum and the slurry was dilute with water (10 mL). The solution was adjusted to pH 9 with a saturated NaHCO3 solution, extracted with ethyl acetate (10 mL¡Á3) for three times, the organic phase was washed with water (10 mL), dried over sodium sulfate, concentrated and purified by column chromatography to give the target compound 3a-3b. 2-Chloro-N-(4-methoxyphenyl)-N-methylpyrimidin-4-amine (3a) White solid. Yield: 79percent. 1H NMR (400 MHz, Chloroform-d) delta 7.85 (d, J = 6.1 Hz, 1H), 7.14 (d, J = 2.2 Hz, 1H), 7.12 (d, J = 2.3 Hz, 1H), 6.99 (d, J = 2.3 Hz, 1H), 6.97 (d, J = 2.2 Hz, 1H), 6.08 (d, J = 6.1 Hz, 1H), 3.85 (s, 3H), 3.44 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 163.86, 160.66, 158.97, 155.98, 136.25, 128.03, 115.50, 103.27, 55.55, 38.35. HRMS (ESI) (m /z) [M+H]+ calcd for C12H12N3OCl, 250.0742; found, 250.0725. Purity: 100.0percent (by HPLC).

The chemical industry reduces the impact on the environment during synthesis 4-Methoxy-N-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Xu, Shaoyu; An, Baijiao; Li, Yuxin; Luo, Xunbang; Li, Xingshu; Jia, Xian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1769 – 1775;,
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5961-59-1, 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. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A round-bottomed flask was charged with the aryl halide (1 mmol),the indoline or (het)aryl amine (1 mmol), and Pd2(dba)3 (0.005mmol, 5 mg). At this point, CH2Cl2 (10 mL) was used to dissolve the reactants and to suspend K2CO3 (4 mmol, 552 mg) and Al2O3 (2g). The CH2Cl2 was then removed under reduced pressure and subsequently recovered. The residual powder was ground with a mortar and pestle for 5 min. A microwave oven reactor was charged with the reactant powder which was compacted as much as possible. The powder was heated at 140 ¡ãC for 20 min at medium power (350 W) ,then charged into a flash silica gel column which was eluted with hexane?EtOAc (4:1) to give the purified product. The solid products were further purified by crystallization from hexane?Et2O.

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Reference:
Article; Basolo, Luca; Bernasconi, Alice; Broggini, Gianluigi; Gazzola, Silvia; Beccalli, Egle M.; Synthesis; vol. 45; 22; (2013); p. 3151 – 3156;,
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