Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 3544-25-0, name is 2-(4-Aminophenyl)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 3544-25-0, Computed Properties of C8H8N2

General procedure: Propionyl chloride (6.0mmol) in dry CH2Cl2 (10mL) was added dropwise to a mixture of 4-methoxybenzenamine (5.0mmol), sodium bicarbonate (12.5mmol) and dry CH2Cl2 (15mL). The mixture was stirred in ice water bath for 1h and poured into water and then extracted with CH2Cl2 (3¡Á30mL). The combined organic layer was washed with brine and dried over anhydrous MgSO4. The solvent was evaporated to dryness to afford the compound 4a. Others amide derivatives 4b-4s were synthesized similarly. Physical constants and spectral data of compounds 4a-4s are summarized below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Aminophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Ji, Qinggang; Yang, Dan; Wang, Xin; Chen, Chunyan; Deng, Qiao; Ge, Zhiqiang; Yuan, Lvjiang; Yang, Xiaolan; Liao, Fei; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3405 – 3413;,
Nitrile – Wikipedia,
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Synthetic Route of 873-32-5, A common heterocyclic compound, 873-32-5, name is 2-Chlorobenzonitrile, molecular formula is C7H4ClN, 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: A 50-mL Schlenk tube was charged with aryl halide (1.63 mmol), aryl boronic acid (2.61 mmol), KOH (3.26 mmol), complex 17d (0.5 mol %), TBAB (0.5 mol % relative to the aryl halide) and water (2 mL). The sealed mixture was stirred at 120 C until TLC analysis confirmed completion of the reaction (for GC analysis the products were extracted with toluene). The aqueous solution was then extracted with ethyl acetate (3 10 mL). The combined organic phases were dried over MgSO4, filtered and evaporated in vacuo. The residue product was purified by column chromatography on silica gel using a mixture of hexane and ethyl acetate as eluent to yield biaryls 23a-m:

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:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 14618-78-1, A common heterocyclic compound, 14618-78-1, name is 4,4-Dimethoxybutanenitrile, molecular formula is C6H11NO2, 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.

Reference Example 68 2-formyl-4,4-dimethoxybutanenitrile Lithium diisopropylamide mono(tetrahydrofuran) (1.5 M in cyclohexane, 22.0 mL, 33.00 mmol) was added to THF (100 mL) at -30 C. and the resulting solution was stirred for 10 min before 3-cyanopropionaldehyde dimethyl acetal (3.90 mL, 29.90 mmol) was added dropwise over 5 min. After 15 min, methyl formate (2.80 mmol, 45.42 mmol) was added and the resulting solution was stirred at -20 C. to -15 C. for 2 h. The reaction mixture was quenched with water (100 mL) and washed with ether (2*50 mL, discarded). The aqueous layer was acidified with 10% HCl and extracted with ether (3*50 mL). The combined ether extracts were washed with brine (3*50 mL), dried (MgSO4), and concentrated. The residue was dissolved in dichloromethane and concentrated to remove traces of THF and provide 2.28 g (49%) of the title compound as a pale yellow oil.

The synthetic route of 14618-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ortho-McNeil Pharmaceutical, Inc.; US6613747; (2003); B2;; ; Patent; Henninger, Todd C.; Xu, Xiaodong; US2002/115620; (2002); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 97165-77-0, name is 3,5-Dibromobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H3Br2N

Compound II – 2 (2.61 g, 10 mmol), compound III (2.06 g, 10 mmol), Pd (OAc)2(0.22 G, 1 mmol), BINAP (2, 2 ‘- bi-phenyl diphenylphosphino – 1, 1’ – binaphthyl, 0.62 g, 1 mmol) and t – BuOK (2.24 g, 20 mmol) is added to the 50 ml dry 1, 2 – dimethoxy ethane (DME), the reaction mixture is stirred under a nitrogen atmosphere overnight, detected in the TLC reaction is completed.The reaction mixture carefully dumped into 200 ml ice water, stirring, for 50 ml ¡Á 3 CH2Cl2Extraction, the combined extraction phase, for sequentially 1% dilute hydrochloric acid and salt is washed with water, dried with anhydrous sodium sulfate. Oil filtration to remove the drying agent, the filtrate on a rotary evaporator to dryness, the residue using silica gel column chromatography purification, to obtain compound IV – 2

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 97165-77-0.

Reference:
Patent; Guangdong Sai Bo Technology Co., Ltd.; Guo Huijun; (8 pag.)CN107903271; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 846023-24-3,Some common heterocyclic compound, 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, molecular formula is C10H8Cl2N2O2, 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.

Isopropanol (80 ml) was added to the reaction flask, and 2-cyano-N- (2,4-dichloro-5-methoxyphenyl) acetamide (10.0 g) and triethyl orthoformate ( 12.03g).The temperature was raised to 80 C, and a solution of isopropylamine (2.4 g) in isopropyl alcohol (60 ml) was added dropwise.Keep stirring for 24h.The system was cooled to room temperature, centrifuged, the solid was dissolved in dichloromethane (130 ml), and separated by column chromatography (n-hexane / ethyl acetate (v / v) = 3: 1) to obtain an off-white solid impurity (I-iPr). .Yield: 94.7%, purity: 99.9%.

The synthetic route of 846023-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Wu Yao; Zhou Ting; Jiang Dongdong; Jin Yanfen; Yang Yong; Chen Yu; (16 pag.)CN110372539; (2019); A;,
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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 1-Amino-1-cyclopropanecarbonitrile hydrochloride

A solution of 2-[3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5- dihydro- 1 H- 1 ,2,4-triazol- 1 -yl } methyl)- IH- 1 ,2,4-triazol- 1 -yl]pyridine-3-carboxylic acid (Example 33A, 80.0 mg, 157 muiotaetaomicron) in N,N-dimethylformamide (1.0 ml) was treated with HATU (89.5 mg, 235 muiotaetaomicron) and stirred 30 min at room temperature. 1-Aminocyclopropanecarbonitrile hydrochloride (1: 1) (27.9 mg, 235 muiotaetaomicron) was then added followed by and N,N- diisopropylethylamine (120 mu, 710 mumol). The resulting mixture was stirred 2 h at room temperature. Purification by preparative HPLC (Method 4) afforded 72.0 mg (80 % of th.) of the title compound. LC-MS (Method 2): Rt = 1.60 min; MS (ESIpos): m/z = 574.1 [M+H]+ -NMR (400 MHz, DMSO-d6) delta [ppm] : 9.23 (d, 2H), 8.64 (dd, IH), 8.08 (dd, IH), 7.83-7.53 (m, 5H), 6.92 (d, IH), 5.08 (s, 2H), 4.41-4.21 (m, IH), 4.08-3.75 (m, 2H), 1.60-1.11 (m, 4H).

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; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; WITTWER, Matthias, Beat; LUSTIG, Klemens; TINEL, Hanna; LINDNER, Niels; SCHIRMER, Heiko; (449 pag.)WO2019/81307; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 3544-25-0, 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. 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1. 4-Hydrazinobenzylcyanide. Hydrochloride A solution of NaNO2 (80 g, 1.16 mol) was added dropwise to a cooled (-10 C.), stirred, suspension of 4-aminobenzyl cyanide (153.5 g, 1.16 mol) in concentrated HCl (1500 ml), at such a rate that the temperature did not rise above -10 C. The mixture was stirred at -10 C. for 0.25 h before being filtered rapidly under vacuum into an addition funnel. The solution was added portionwise over a 0.25 h period to a rapidly stirred mixture of SnCl2.2H2 O (1.05 kg, 4.64 mol) in concentrated HCl (800 ml) keeping the temperature below -5 C. The mixture was allowed to warm to room temperature and stir for 0.25 h before filtering the sandy coloured precipitate under vacuum and washing with ether (5*500 ml). The resultant solid was dried over P2 O5 in a vacuum oven (80 C.) for 16 h to give the title compound (213 g, 100%), m.p. 181-183 C.; 1 H NMR (360 MHz, D2 O) delta 3.90 (2H, s, CH2); 7.06 (2H, d, J=8.7 Hz, Ar-H); 7.40 (2H, d, J=8.7 Hz, Ar-H).

The synthetic route of 2-(4-Aminophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Limited; US5298520; (1994); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 53312-79-1, 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. 53312-79-1, name is 3-Amino-4-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j00316j A mixture of 3-amino-4-chlorobenzonitrile (1.0 g, 6.6 mmol) and potassium 0-ethyl carbonodithioate (2.1 g, 13.1 mmol) in 1-methylpyrrolidin-2-one (5 mL) at 25 C was degassed and purged with nitrogen 3 times. The mixture was stirred at 120 C for 10 hours, then poured into ice water (200 mL) and acidified with 1 mL concentrated hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration, washed with water (3 x 10 mL) and dried in vacuo to give compound B-22 (1.1 g, crude) as a yellow solid, which was used directly without further purification. LCMS (B): tR=0.613 mi, (ES) mz (M+H) = 193.1.

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

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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. 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Bromo-5-fluorobenzonitrile

General procedure: To a solution of 5 (500 mg, 2.55 mmol) in 10 mL of DMF was successively added Et3N (1.42 mL, 10.2mmol), 9a (579 mg, 2.55 mmol), CuI (48 mg, 0.25 mmol), and trans-dichlorobis(triphenylphosphine)palladium (177 mg, 0.25 mmol). The resulting solution was warmed to 60 oC, and TBAF 1M in THF (2.8 ml, 2.80mmol) was added dropwise. After 2h at this temperature the mixture was hydrolyzed with 50 mL of H2O and, extracted with AcOEt (4 X 30 mL). The organic layer was washed with saturated NaCl (3 X 30 mL), dry over anhydrous Na2SO4, and concentrated on a rotary evaporator. Purification of the residue by column chromatography (hexane/AcOEt 8/2) yielded 439 mg (64 %) of 1a as an off white solid. 1H NMR (CDCl3), d = 2.67 (s, 3H, CH3); 7.46 (s, 1H, CHAr); 8.00 (t, 1H, J= 1.6 Hz, CHAr); 8.35 (t, 1H, J=1.6 Hz, CHAr); 8.47 (t, 1H, J=1.6 Hz, CHAr). 13C NMR (CDCl3), d = 19.6 (1C, CH3); 84.6 (1C, C?C); 89.1 (1C, C?C); 114.8 (1C, Cq); 116.3 (1C, Cq); 125.5 (1C, CHAr); 126.5 (1C, CHAr); 126.6 (1C, CHAr); 130.4 (1C, CHAr); 135.4 (1C, Cq); 140.1 (1C, CHAr); 148.6 (1C, Cq); 166.9 (1C, Cq). Anal (C13H7N3O2S, HCl) C, H, N.

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; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 90401-84-6, name is 6-Cyano-1-tetralone, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C11H9NO

Step 3: 6-Bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile Bromine (0.8 mL, 15.7 mmol) was added to a solution of 5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile (2.7 g, 15.7 mmol), prepared in the previous step, in dry methylene chloride (55 mL) at 0 C. The reaction was warmed to room temperature. After 2 h, the reaction was diluted with methylene chloride and washed with 5% sodium thiosulfate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 4.3 g of crude product. Purification of the crude product on silica gel using 10% ethyl acetate:hexane as the eluent gave 6-bromo-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (3.2 g, 81%), MS(ES) m/z 251 [M+H]+.

According to the analysis of related databases, 90401-84-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2008/45578; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts