The origin of a common compound about 621-50-1

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, 2-(3-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, 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 621-50-1, Recommanded Product: 2-(3-Nitrophenyl)acetonitrile

A. (3-Amino-phenyl)-acetonitrile A mixture of (3-nitro-phenyl)-acetonitrile (2.00 g, 12.35 mmol), iron dust (2.07 g, 37.03 mmol) and ammonia chloride (1.96 g, 37.03 mmol) in EtOH (20 mL) and water (4 mL) was refluxed at 85 C. for 1 h. The reaction mixture was filtered through cellite and rinsed with EtOH. The combined filtrate was concentrated and the residue was purified by silica gel column chromatography (20% ethyl acetate in petroleum ether) to afford the title compound (1.57 g, 11.89 mmol, 96% yield) as a pale-yellow solid. MS (ESI) m/z 133.1 [M+H]+.

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, 2-(3-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Papa, Patrick; Cathers, Brian Edwin; CALABRESE, Andrew Antony; WHITEFIELD, Brandon Wade; BENNETT, Brydon; CASHION, Daniel; MORTENSEN, Deborah; HUANG, Dehua; TORRES, Eduardo; PARNES, Jason; SAPIENZA, John; HANSEN, Joshua; LEFTHERIS, Katerina; CORREA, Matthew; DELGADO, Maria Mercedes; RAHEJA, Neil; BAHMANYAR, Sami; HEGDE, Sayee; NORRIS, Stephen; PLANTEVIN-KRENITSKY, Veronique; US2015/175557; (2015); A1;,
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Discovery of 332-25-2

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

Related Products of 332-25-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 332-25-2 name is 4-(Trifluoromethoxy)benzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 2:; To a stirred solution of N,N-diethyl-4-methoxy-2-methyl-benzamide (10.0 g, 45.2 mmol) in THF (150 mL) at -78° C. under nitrogen atmosphere was added t-BuLi (29.2 mL of 1.7M in pentane, 49.7 mmol) dropwise. The resulting red solution was kept at this temperature for additional 10 min before dropwise addition of 4-(trifluoromethoxy)-benzonitrile (9.49 g, 49.7 mmol). The brown solution was stirred at -78° C. for 2 h; tests by LCMS showed incomplete reaction. Thus to the mixture was added an additional amount of 4-(trifluoromethoxy)-benzonitrile (3.38 g, 18.1 mmol) and the resulting mixture was stirred for an additional 1 h. The mixture was then allowed to warm to rt and was quenched by pouring into aqueous 1.0M HCl (50 mL). EtOAc (100 mL) was added and the mixture was shaken and phases were separated. A precipitate occurred within the EtOAc phase which was isolated by filtration and allowed to dry (3.0 g). This 3.0 g of isolated solid was determined to be impure product and was set aside for later purification. The EtOAc filtrate was set aside. The aqueous acid washes were combined and extracted with DCM (3.x.100 mL). The DCM extracts were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. This residue was combined with the original EtOAc filtrate and the combined organics were concentrated to a slurry. A solid was isolated by filtration to give the desired product (8.84 g, 58.0percent yield). LC-MS, MS m/z 336 (M++H).

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

Reference:
Patent; Bristol-Myers Squibb Company; US2008/119461; (2008); A1;,
Nitrile – Wikipedia,
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A new synthetic route of 6393-40-4

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, 4-Amino-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Adding a certain compound to certain chemical reactions, such as: 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, 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 6393-40-4, category: nitriles-buliding-blocks

3-Nitro-4-aminobenzonitrile (3.00 g) was dissolved in ethanol (300 ml) and added with stannous chloride dihydrate (20.7 g) and the whole was heated to 60C. Sodium borohydride (348 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was added with water (300 ml) and neutralized with a 5 mol/l sodium hydroxide aqueous solution. After ethanol was distilled off under reduced pressure, the aqueous layer was added with ethyl acetate for extraction. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was recrystallized, thereby obtaining the subject compound (1.11 g) as a brown crystal. MS(EI):m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8,1Hz),6.95(1H,s),7.05(1H,d,J=8.1Hz).3-Nitro-4-amino-benzonitrile (4.38 g) was dissolved in ethanol (600 ml) and added with stannous chloride dihydrate (34.6 g) and the whole was heated to 60C. Sodium borohydride (366 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was filtrated through Celite and the filtrate was subjected to distillation of the solvent under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was allowed to recrystallize (hexane/ethyl acetate), thereby obtaining the subject compound (2.56 g) as a brown crystal. MS (EI) :m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8.1Hz),6.95(1H,s),7.05(1H, d,J=8.1Hz).An ethanol solution (300 ml) containing 4-amino-3-nitrobenzonitrile (3.00 g) was added with stannous chloride dihydrate (20.7 g) and then added with sodium borohydride (348 mg) . The whole was stirred overnight at 60C. After that, the resultant was subjected to distillation until the amount of the solution became about 100 ml. The resultant was added with water (100 ml) and a large amount of solid component was generated. The resultant was added with a 5 mol/l sodium hydroxide aqueous solution (42 ml) to adjust to pH 7. The solvent was distilled off. The solid component was filtrated out through Celite and washed with methanol and ethyl acetate in the stated order. The filtrate was again filtrated through Celite and only organic solvent was distilled off under reduced pressure. The remaining aqueous layer was subjected to extraction with ethyl acetate and dried with anhydrous magnesium sulfate , and the solvent was distilled off, thereby obtaining the subject compound (2.29 g) as a khaki crystal.

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, 4-Amino-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Nitrile – Wikipedia,
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Share a compound : 96606-37-0

The synthetic route of 96606-37-0 has been constantly updated, and we look forward to future research findings.

Electric Literature of 96606-37-0,Some common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

In analogy to GP1a, 5 g of 2,4,6-trifluorobenzonitrile (31.83 mmol, 1 eq; commercially available) and 4.45 ml of 2-((R)-2,2-Dimethyl-[1 ,3]dioxolan-4-yl)-ethanol (31.83 mmol, 1 eq; commercially available) were dissolved in 150 ml of THF, treated with 2.78 g sodium hydride (62.66 mmol; 2 eq.) and stirred at rt for 2 h. The reaction mixture was poured onto 50 ml of water and extracted three times with 100 ml of ethyl acetate each. The organic layer was washed twice with brine, dryed over sodium sulfate, filtered off to afford 5.21 g (57.79% yield, 18.39 mmol) of the desired product.1H-NMR (dbeta-DMSO; 300 MHz): 6.52 – 6.57 (m, 2 H); 4.30 – 4.36 (m, 1 H); 4.10 – 4.23 (m, 3 H); 3.67 (dd, 1 H); 2.11 – 2.20 (m, 1 H); 2.00 – 2.08 (m, 1 H); 1.42 (s, 3 H); 1.35 (s, 3 H).MS (ESI): [M+H]+ = 284.

The synthetic route of 96606-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAYER HEALTHCARE AG; WO2008/138639; (2008); A1;,
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Extended knowledge of 14618-78-1

According to the analysis of related databases, 14618-78-1, the application of this compound in the production field has become more and more popular.

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 14618-78-1 as follows. name: 4,4-Dimethoxybutanenitrile

General procedure: One equiv. of carbazate was suspended in EtOH containing 10% (by vol.) of water(approx. 5 ml per mmol of the carbazate) and 1.05 equiv. of the acetal or ketal wasadded, followed by the addition of 0.05 equiv. of TFA. The reaction mixture was heatedto reflux and the progress of the reaction was monitored by TLC (thin layer chromatographyon silica gel) using ethyl acetate or a mixture of ethyl acetate-light petroleummixture (for the correct eluent, see characterization data of the compounds). After thereaction was complete, the reaction mixture was cooled to about 45C and three (3)equiv. of acetic acid was added, followed by the dropwise addition of a THF solutionof three (3) equiv. of NaBH3CN (approx. 1 ml of THF per 1.5 mmol of NaBH3CN).The reaction mixture was stirred at approx. 45C for 80 min. Subsequently, the reactionmixture was cooled to room temperature, acidified using 0.5 M HCl aqueous solution(6 ml of 0.5 M HCl per 1 mmol of starting carbazate) and stirred until the liberation ofhydrogen ceased. The reaction mixture was neutralized (to pH 8) by the dropwise additionof a saturated NaHCO3 solution (4 ml per 1 mmol of carbazate). The volatileswere removed under reduced pressure at approx. 40C. The residue was dissolved inethyl acetate, washed with saturated NaHCO3, twice with water and finally with saturatedaqueous sodium chloride. The combined aqueous washes were extracted twicewith ethyl acetate (25 ml per 1 mmol of expected product) and the extracts werewashed with saturated aqueous sodium chloride and combined with the organic phase. After drying over anhydrous Na2SO4 and evaporation of the solvent under reduced pressure,the residue was purified by column chromatography on silica gel using ethyl acetate-light petroleum (1:1 or 1:2) or ethyl acetate as eluent. For specific informationabout the eluent used to monitor the progress of the reaction and for purification, seethe Rf data for each compound.

According to the analysis of related databases, 14618-78-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 47; 6; (2015); p. 490 – 498;,
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New downstream synthetic route of C8H6BrN

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

These common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, 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. SDS of cas: 19472-74-3

To a stirred solution of (2-bromophenyl)-acetonitrile (13) (5 g, 25.51 mmol) in a mixture of toluene and ethanol (1:1, 150 mL) was added 2-chloro phenyl boronic acid (14) (6 g, 38.2 mmol) and Na2CO3 (8.1 g, 76.53 mmol) at room temperature. Purging was conducting for 30 min with nitrogen. Then triphenyl phosphine (2.6 g, 10.2 mmol) was added followed by Pd(OAc)2 (0.287 g, 1.27 mmol) and further degassing was conducted for another 10 min. The reaction mixture was heated to reflux for 10 h. After completion of the reaction, the mixture was concentrated under reduced pressure to get a crude product which was purified using a silica column using 2% ethyl acetate in hexane to get (2?-chloro-biphenyl-2-yl)-acetonitrile (15) (4.9 g, 84.36%) as a yellow liquid.

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

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); A1;,
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Analyzing the synthesis route of 53312-80-4

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 53312-80-4.

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. 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Amino-2-fluorobenzonitrile

General procedure: A solution of quinolin-5-amine(7, 250 mg, 1.73 mmol) and TEA (200 L, 2.03 mmol) dissolved in CH2Cl2 (DCM, 15 mL) wasslowly dripped into a stirred solution of triphosgene (BTC, 256 mg, 0.85 mmol) in DCM (10 mL)by using a constant-pressure dropping funnel. Then, the mixture was stirred for another 0.5 h at room temperature (RT). After evaporation of the solvent, the residue was taken up in DCM (30 mL),and (5-(2,5-dichlorophenyl)furan-2-yl)methanamine (5b, 230 mg, 0.95 mmol) was added directly to the residue. The reaction mixture was stirred at RT for 6 h, and the solvent was subsequently removed in vacuo. The residue obtained was purified by column chromatography (V(PE):V(EA) = 1:1) to give the desired target compound 12 (343 mg, 0.84 mmol) in 88% yield. 96.8% HPLC purity.

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 53312-80-4.

Reference:
Article; Wang, Lijiao; Li, Chao; Chen, Wei; Song, Chen; Zhang, Xing; Yang, Fan; Wang, Chen; Zhang, Yuanyuan; Qian, Shan; Wang, Zhouyu; Yang, Lingling; Molecules; vol. 24; 15; (2019);,
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Introduction of a new synthetic route about 623-26-7

The synthetic route of 623-26-7 has been constantly updated, and we look forward to future research findings.

623-26-7, name is Terephthalonitrile, belongs to nitriles-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. Recommanded Product: Terephthalonitrile

Example 38 Terephthalonitrile (12.8 g), hydrogen chloride gas (2.24 NL), and ethanol (72.5 g) were placed in a glass autoclave, and the mixture was allowed to react at 130 C. for six hours. The reaction mixture was cooled, and water (9 g) was added thereto. Gas chromatographic analysis revealed that ethyl p-cyanobenzoate had been produced at a yield of 30% and a selectivity of 96%.

The synthetic route of 623-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Showa Denko Kabushiki Kaisha; US6433211; (2002); B1;,
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Introduction of a new synthetic route about 34403-48-0

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Application of 34403-48-0, A common heterocyclic compound, 34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, molecular formula is C9H10N2, 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.

Compound 489 5-(chloromethyl)-6-phenylimidazo[1,5-a]pyridine 55b (25 mg, 0.103 mmol), 491 4-((methylamino)methyl)benzonitrile (29 mg, 0.2 mmol), 27 K2CO3 (69 mg, 0.5 mmol) and 149 acetonitrile (5 mL) were mixed at room temperature, heated to 55 C. and stirred for 18 h. After cooled to room temperature, the mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1 to 1/3) to give the target 492 product 4-((methyl((6-phenylimidazo[1,5-a]pyridin-5-yl)methyl)amino)methyl)benzonitrile 55 (25 mg, light yellow oil). Yield: 71%.MS m/z (ESI): 353[M+1]1H NMR (400 MHz, CDCl3) delta 8.64 (s, 1H), 7.64-7.42 (m, 7H), 7.38-7.22 (m, 4H), 6.70 (d, J=9.2 Hz, 1H), 3.89 (s, 2H), 3.44 (s, 2H), 2.11 (s, 3H).

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Innocare Pharma Tech Co., Ltd.; CHEN, Xiangyang; GAO, Yingxiang; US2019/185472; (2019); A1;,
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Extended knowledge of 4-Bromobutanenitrile

The synthetic route of 5332-06-9 has been constantly updated, and we look forward to future research findings.

5332-06-9, name is 4-Bromobutanenitrile, belongs to nitriles-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. SDS of cas: 5332-06-9

Example 10; 4-Azidobutanenitrile (22).; Sodium azide (1.2 g, 18.5 mmol) was added to a solution of 4-bromobutyronitrile (20, 1.8 g, 12.0 mmol) in DMSO (20 mL). After 18 h of stirring at room temperature, water (40 mL) was added, and the solution was extracted with diethyl ether. Evaporation of the solvent gave 22 as a light yellow oil EPO (0.9 g, 67%). IH NMR (400 MHz, CDCl3) £3.5 (t, 2H, J= 6.0 Hz), 2.5 (t, 2H, J= 7.2 Hz), 1.90 – 1.95 (m, 2H).

The synthetic route of 5332-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHWESTERN UNIVERSITY; WO2007/35964; (2007); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts