Month: December 2020

Synthetic Route of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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 lithium 3-[(2-Dimethylamino-ethyl)-methyl-amino]-lH-indazole- 6-carboxylate (77mg, 0.29 mmol) in anhydrous DMF (5mL) was added EDC (140mg, 0.73mmol) and etaOBt (47mg, 0.35mmol). The mixture was stirred for 10 min. then Et3N (0.16mL, 0.1.16mmol) and 4-trifluoromethoxybenzylamine (0.049mL, 0.32 mmol) were added. The mixture was heated at 50 0C for 15 hr. The mixture was allowed to cool, diluted with ethyl acetate (50 mL) and washed with aqueous sodium bicarbonate (25 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography on silica yielded the title compound (37mg, 29%). m/z (M+eta) = 436.45.

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

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61109; (2008); A2;,
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Some common heterocyclic compound, 216067-66-2, name is O-(2,4-Dimethoxybenzyl)hydroxylamine, molecular formula is C9H13NO3, 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. Application In Synthesis of O-(2,4-Dimethoxybenzyl)hydroxylamine

General procedure: To a solution of 2a (0.200 g, 0.651 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl, 0.150 g, 0.781 mmol)and 4-dimethylaminopyridine (DMAP, 8 mg, 0.065 mmol) in CH2Cl2(30 mL) was added O-benzylhydroxylamine hydrochloride (0.125 g;0.781 mmol) and N-methylmorpholine (NMM, 0.086 mL, 0.781 mmol),and the mixture was stirred at room temperature (r.t.) for 16 h. Thefinal solution was evaporated, dissolved in EtOAc (25 mL) and washedwith 0.1 M HCl (3 ¡Á 25mL), 0.1 M NaOH (2 ¡Á 25 mL) and then H2O(1 ¡Á 25 mL). The final organic phase was dried over anhydrous Na2SO4,and the solvent evaporated. The crude was recrystallized from Et2O/n-hexane, affording the pure compound 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 216067-66-2, its application will become more common.

Reference:
Article; Marques, Sergio M.; Abate, Claudia C.; Chaves, Silvia; Marques, Fernanda; Santos, Isabel; Nuti, Elisa; Rossello, Armando; Santos, M. Amelia; Journal of Inorganic Biochemistry; vol. 127; (2013); p. 188 – 202;,
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Electric Literature of 1836-62-0, A common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, molecular formula is C9H13NO2, 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.

General procedure: Et3N (4.3 mmol) and 97% EtOCOCl (4.3 mmol) in dry CHCl3(25 mL) were added to a solution of the suitable carboxylic acid 24a,24b or 25 (4.3 mmol) at 0 C. After 30 min at 0 C under stirring asolution of the suitable amine (2-phenoxyethanamine, 2-(2-methoxyphenoxy)ethanamine [37], 2-(2,6-dimethoxyphenoxy)ethanamine [38], or 1-(2-methoxyphenyl)piperazine) (4.3 mmol)in dry CHCl3 (10 mL) was added and the reaction mixture was left atroom temperature for 3 h. The solution was washed with 2 N HCl and 2 N NaOH. The organic layer was dried over Na2SO4. After evaporation of the solvent the residue was purified by column chromatography eluting with cyclohexane/EtOAc (7:3).

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Del Bello, Fabio; Bonifazi, Alessandro; Giorgioni, Gianfabio; Quaglia, Wilma; Amantini, Consuelo; Morelli, Maria Beatrice; Santoni, Giorgio; Battiti, Francisco O.; Vistoli, Giulio; Cilia, Antonio; Piergentili, Alessandro; European Journal of Medicinal Chemistry; vol. 168; (2019); p. 461 – 473;,
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Related Products of 20012-63-9,Some common heterocyclic compound, 20012-63-9, name is 2-(Benzyloxy)aniline, molecular formula is C13H13NO, 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.

A solution of this acid chloride in dry methylene chloride (65 ml) was added to a stirred mixture of 2-benzyloxyaniline [3.0 g; prepared as described by Barber et al., J. Chem. Soc., (1961), 2828], pyridine (1.36 g) and dry methylene chloride (65 ml) at 0 C. The mixture was stirred at 10 C. for 2 hours and then was allowed to stand at room temperature overnight. The mixture was washed twice with water and the methylene chloride solution was then dried over magnesium sulphate and evaporated under diminished pressure. The resulting solid was recrystallized from ethanol to give 1-benzyl-2′-benzyloxy-1H-tetrazole-5-carboxanilide (3.1 g), m.p. 140-142 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Benzyloxy)aniline, its application will become more common.

Reference:
Patent; May & Baker Limited; US4442115; (1984); A;,
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Synthetic Route of 450-91-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 450-91-9 as follows.

Under an ice bath condition, 4-fluoro-2-methoxyaniline (Intermediate 102) (15 g, 106.4 mmol, 1.0 eq) was added dropwise to a concentrated sulfuric acid (150 mL) while controlling the temperature around 0C during the course of addition. After the forming solid was dissolved completely, potassium nitrate (11 g, 106.4 mmol, 1.0 eq) was added portionwise and the reaction was continued for 1 hour under this condition. The reaction was poured into ice water and the pH was adjusted to basic by sodium hydroxide. A vast amount of solid was precipitated out which was filtered and washed with water, petroleum ether, dried in air to give 4-fluoro-2-methoxy-5-nitroaniline as a brown solid (18 g, yield: 77%). LCMS (ESI): m/z 187 [M + H]+.

According to the analysis of related databases, 450-91-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Bebetter Medicine Technology Co., Ltd.; CAI, Xiong; QIAN, Changgeng; WENG, Yunwo; LIU, Bin; WANG, Yanyan; LIN, Mingsheng; LI, Junqi; QING, Yuanhui; YOU, Huajin; ZHOU, Shiqing; XUE, Weicai; (76 pag.)EP3345900; (2018); A1;,
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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. 7664-66-6, name is 4-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Isopropoxyaniline

Step 1 (4-isopropoxyphenyl)hydrazine hydrochloride To a stirred solution of 4-(propan-2-yloxy)aniline (5.0 g, 33.07 mmol, 1.00 equiv) in 2N hydrochloric acid (35 mL) at 0 C. was added dropwise a solution of sodium nitrite (2.4 g, 34.78 mmol, 1.05 equiv) in water (8 mL). The reaction mixture was stirred at 0-5 C. for 1 h. A solution of SnCl2.H2O (15 g, 66.37 mmol, 2.01 equiv) in 12N hydrochloric acid (20 mL) was then added dropwise at 0-5 C. The resulting mixture was stirred at room temperature overnight. The precipitates was collected by filtration to give 4.7 g (70%) of crude (4-isopropoxyphenyl)hydrazine hydrochloride as a purple solid. The product was used in the next step without further purification.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Chesworth, Richard; Mitchell, Lorna Helen; Shapiro, Gideon; US2014/315961; (2014); A1;,
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Electric Literature of 2688-84-8, 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. 2688-84-8, name is 2-Phenoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1.0 equivalent of intermediate Bn-2 and172.5 g (3.0 eq.) of p-toluenesulfonic acid hydrate (PTSA*H2O) was mixed in 224 ml of a 1.3 M acetonitrile (ACN) solution and cooled to 5 C in an ice bath.41.7 g (2 equivalents) of sodium nitrite (NaNO2) was dissolved in 240 ml of water and added dropwise.After the completion of the dropwise addition, the ice bath at 5 C was maintained for 1 hour, and the aqueous solution of the diazonium salt after the reaction was treated with 100 g (2 equivalents) of potassium iodide (KI) in 300 ml of an aqueous solution, followed by extraction with ethyl acetate. The combined organic phases were washed with aq. 10% aqueous sodium sulphate and dried over sodium sulfate, and then filtered and evaporated. The chemical structural formula of the reactant An for synthesizing the intermediate Bn (especially referring to the intermediates B1 to B4) and the chemical structural formulas and yields of the intermediates Bn-1, Bn-2 and Bn are listed in Table 2-1.

The synthetic route of 2-Phenoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NICHEM FINE TECHNOLOGY CO., LTD.; LU, TAI-NI; WU, HUI-LING; SHIEH, SHWU-JU; CHEN, CHI-CHUNG; (84 pag.)TWI644912; (2018); B;,
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Related Products of 19500-02-8, The chemical industry reduces the impact on the environment during synthesis 19500-02-8, name is 3-Methoxy-2-methylaniline, I believe this compound will play a more active role in future production and life.

A. N-tert-butoxycarbonyl-3-methoxy-2-methylaniline. A solution of 44.4 g (344 mmol) of 3-methoxy-2-methylaniline and 75 g (344 mmol) of di-tert-butyl dicarbonate in 400 mL of THF was heated to maintain reflux for 4 hours. After concentrating at reduced pressure, the residue was taken up in ethyl acetate, washed with 1N citric acid, water and dried (MgSO4). After removing the solvent at reduced pressure, the residue was crystallized from hexane to give 64.5 g (84percent yield) of N-tert-butoxycarbonyl-3-methoxy-2-methylaniline, mp, 56¡ã-57¡ã C. Analysis for C13 H19 NO3: Calculated C, 65.80; H, 8.07; N, 5.90. Found C, 63.32; H, 7.83; N, 5.56.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Methoxy-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eli Lilly and Company; US5684034; (1997); 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. 295376-21-5, name is 1-Bromo-2-fluoro-3-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 295376-21-5

A compound of formula 6a (20.50 g, 100 mmol), 7a (15.62 g, 120 mmol) and dimethyl sulfoxide (102 mL) were added to a three-neck flask.After stirring and stirring, cuprous iodide (1.90 g, 10 mmol), L-valine (1.15 g, 10 mmol), potassium carbonate (27.64 g, 200 mmol),Vacuum switching nitrogen 3 times,The temperature is raised to 45 to 50 C for 6 to 8 hours.After completion of the reaction, the reaction was quenched by the addition of ammonium chloride solution (204 mL), and extracted with ethyl acetate (102 mL), and the organic phase was combined and washed with saturated brine.Then, dry anhydrous sodium sulfate, concentrated to remove some solvent under reduced pressure, add petroleum ether to be beaten, filter, collect solids and dry to produce Product 8a (21.66 g, 74%).

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; Hangzhou Kechao Biological Technology Co., Ltd.; Zheng Xuchun; Zhang Yiping; Fu Chenchen; (12 pag.)CN108586359; (2018); A;,
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Electric Literature of 6298-96-0, A common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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.

Preparation Example 174 To 713 mg of methyl 1-oxoindane-5-carboxylate were added 612 mg of (1S)-1-(4-methoxyphenyl)ethanamine, 0.23 ml of acetic acid, 600 mg of Molecular Sieves 4A, and 12 ml of toluene, followed by heating to reflux using a Dean-Stark type reflux device for 4 hours under reduced pressure (213 mbar). Then, 0.23 ml of acetic acid and 300 mg of Molecular Sieves 4A were added thereto, followed by heating to reflux using a Dean-Stark type reflux device for 4 hours under reduced pressure (213 mbar). The insoluble material was removed by filtration and the solvent was then evaporated under reduced pressure to obtain an intermediate product. To a solution of the obtained intermediate product in 13 ml of ethanol was added 161 mg of sodium borohydride under ice-cooling, followed by stirring for 1 hour under ice-cooling. The solvent was evaporated under reduced pressure, and to the obtained residue were added water, a saturated aqueous sodium hydrogen carbonate solution, and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 452 mg of methyl (1S)-1-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-5-carboxylate.

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTELLAS PHARMA INC.; KOGA, Yuji; MAENO, Kyoichi; SATO, Ippei; IMAMURA, Yoshimasa; HANAZAWA, Takeshi; IIDA, Maiko; OHNE, Kazuhiko; IMAMURA, Kenichiro; WATANABE, Tsubasa; NOZAWA, Eisuke; SHIBATA, Hiroshi; US2014/88080; (2014); A1;,
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