Author: Jessica.F

Synthetic Route of 151-18-8,Some common heterocyclic compound, 151-18-8, name is 3-Aminopropanenitrile, molecular formula is C3H6N2, 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 DMF (1.6 mL) solution of 3-(2-[[3-(trifluoromethyl)phenyl]amino][1,2,4]triazolo[1,5-a]pyridin-8-yl)benzoic acid (80 mg, 0.201 mmol) obtained in Reference Example 122, 3-aminopropanenitrile (0.016 mL, 0.221 mmol), HATU (91.6 mg, 0.241 mmol), and N,N-diisopropylethylamine (0.042 mL, 0.241 mmol) was stirred for 3 hours at room temperature. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off at reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from hexane and ethyl acetate to give 68.4 mg of the titled compound (yield 76%) in solid form. Melting point: 214-215 C.1H-NMR (DMSO-d6) delta: 2.81 (2H, t, J=6.5 Hz), 3.55 (2H, q, J=6.5 Hz), 7.15-7.26 (2H, m), 7.53 (1H, t, J=8.0 Hz), 7.65 (1H, t, J=8.0 Hz), 7.89-7.97 (3H, m), 8.21 (1H, br s), 8.34-8.41 (1H, m), 8.49 (1H, t, J=1.6 Hz), 8.89 (1H, dd, J=6.7, 1.0 Hz), 8.99 (1H, t, J=5.7 Hz), 10.22 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2010/41891; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 102151-33-7, name is 3-Chloro-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 102151-33-7, name: 3-Chloro-4-methoxybenzonitrile

Step 1 To a solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (9 ml) at -78 C. was added dropwise tert-butyllithium 1.7 M in pentane (3.19 ml, 5.42 mmol) and the solution was stirred for 0.5 h before addition of 3-chloro-4-methoxybenzonitrile (0.757 g, 4.52 mmol) in THF (9 ml). The resulting solution was warmed to rt and stirred for 16 h. The reaction mixture was quenched with water, neutralized with 1 N HCl. The precipitated solid was collected and washed with water to give 3-(3-chloro-4-methoxyphenyl)-6-methoxyisoquinolin-1-ol (1.2 g, 84% yield) as a solid after drying. MS: MS m/z 316.1 (M++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-Chloro-4-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 3544-25-0,Some common heterocyclic compound, 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, molecular formula is C8H8N2, 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.

(4-Amino-phenyl)-acetonitrile (2 g, 15.1 mmol) and dibenzyl dicarbonate (4.33 g, 15.1 mmol) dissolved in dioxane (16 mL) are stirred for 1 hour at RT. After evaporating the solvent, the product is isolated by flash chromatography (silica gel, 4.5×25 cm, CH2Cl2/MeOH=99:1): white solid (3.82 g, 14.4 mmol; 95%); ES-MS: M-H=265.0; Rf(CH2Cl2/MeOH=95:5)=0.49; HPLC: AtRet=6.32 minutes. 1H-NMR (400 MHz, DMSO-d6): 9.82 (s, 1H, NH), 7.51-7.35 (m, 7H, aryl), 7.26 (d, 8.5 Hz, 2H, aryl), 5.15 (s, 2H, CH2), 3.95 (s, 2H, CH2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Aminophenyl)acetonitrile, its application will become more common.

Reference:
Patent; Bold, Guido; Floersheimer, Andreas; Furet, Pascal; Imbach, Patricia; Masuya, Keiichi; Schoepfer, Joseph G.; US2005/222171; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 75344-77-3, A common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

Step A: 4-bromo-3.5-dimethylbenzamide To a solution of 4-bromo-3, 5- dimethylbenzonitrile (1.0 g, 4.8 mmol) in DMSO (10 ml) at 0 C was added 35% H202 (0.542 mL, 6.19 mmol) and K2C03 (1.32 g, 9.52 mmol). The resulting mixture was stirred at 20 C for2 hours and then poured into water (50 mL). The resulting solid was collected by filtration, then washed with water twice, dried in an oven to give the title compound. ?H NMR (400MHz, CD3OD) oe: 7.62 (s, 2H), 2.46 (s, 6H).

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; MERCK SHARP & DOHME CORP.; BIFTU, Tesfaye; BIJU, Purakkattle; COLLETTI, Steven, L.; DANG, Qun; DHONDI, Pawan, K.; GUDE, Candido; JOSIEN, Hubert; KAR, Nam Fung; NAIR, Anilkumar, G.; NARGUND, Ravi, P.; YANG, De-Yi; XIAO, Dong; ZHU, Cheng; WO2015/73342; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 326-62-5, 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. 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2- (2-fluorophenyl) acetonitrile (5.4 g, 40 mmol) in anhydrous THF (50 mL) was added dropwise of LDA (26 mL, 52 mmol, 1.3 eq) at -78. After addition, the mixture was stirred at -78 for 0.5 h. Then methyl benzoate (6.0 g, 44 mmol, 1.1 eq) in THF (10 mL) was added slowly and stirred at RT overnight. The suspension was quenched with NH4Cl solution (30 mL) and extracted with EA. The organic phase was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 2- (2-fluorophenyl) -3-oxo-3-phenylpropanenitrile (12 g, crude) which was used directly to the next step without further purification. LC-MS: m/z 240.1 (M+H) +.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Fluorophenyl)acetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; TRAVINS, Jeremy, M.; KONTEATIS, Zenon, D.; SUI, Zhihua; YE, Zhixiong; (199 pag.)WO2018/39972; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 14618-78-1, 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. 14618-78-1 name is 4,4-Dimethoxybutanenitrile, 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.

In a 500 ml four-necked flask,Add 100 grams of tetrahydrofuran,13.0 g (0.1 mol) of 4,4-dimethoxy-n-butyronitrile,13.0 g (0.1 mol) of 2,3-dichloropropenal,0.5 g DBU,Reaction at 60 C for 4 hours,The gas phase detection 1,4-addition reaction is completed.Cool down to 25-30 C,Add 15.0 grams of potassium carbonate,25.0 grams of 17% ammonia,8.0 grams of ammonium chloride,Reaction at 50 C for 5 hours,Cool down to 20-25 C,filter,20 grams of ice water wash filter cake,dry,Obtained 13.5 g of 5-chloro-7-azaindole,The liquid phase purity is 99.7%,The yield was 88.5%.

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

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Qi Yuxin; Zhang Mingfeng; Wang Sheng; Li Guangqian; Ju Lizhu; (7 pag.)CN110128421; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 16588-02-6

3-Cyano-4-chloroaniline 2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70 C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3*100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 1080-74-6,Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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 degassed solution of intermediate 1 (0.13 g, 0.1 1 mmol) and 3- (dicyanomethylidene)indan-l -one (1 .5 g, 0.77 mmol) in chloroform (12 cm3) is added pyridine (0.6 cm3, 8 mmol). The mixture is then degassed with nitrogen for 30 minutes and then heated at 70 C for 15 hours. The reaction mixture allowed to cool to 23 C and the solvent removed in vacuo. The crude is purified by column chromatography (40-60 petrol :chloroform; 1 : 1 ) to give compound 75 (1 .1 g, 65%) as a dark blue crystalline solid. 1H NMR (400 MHz, CDCIs) 8.87 (2H, s), 8.69 (2H, d, J 7.6), 7.91 (2H, d, J 7.1 ), 7.68 – 7.79 (6H, m), 7.08 – 7.18 (16H, m), 2.60 (8H, t, J 7.7), 1 .62 (8H, q, J 7.1 Hz), 1 .21 – 1 .39 (40H, m), 0.88 (12H, t, J 6.5).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 51762-67-5 as follows. Recommanded Product: 51762-67-5

3-nitrophthalonitrile (0.500 g, 2.888 mmol) was dissolved in anhydrous dimethylformamide (75 mL) under Ar and hydroxymethyl-EDOT (0.500 g, 2.903 mmol) was added. After stirring for 10 min, finely ground anhydrous K2CO3 (1.200 g, 8.682 mmol) was added in portions over 2 h with efficient stirring. The reaction mixture was stirred at room temperature for 120 h under Ar. Then the solution was poured into ice-water. The resulting white solid was collected by filtration and washed first with water and then with hexane. Yield 0.493 g (57%). Mp: 192 C. FT-IR: numax, cm-1 3116.56 (CH, aromatic), 2963.20 (CH, aliphatic), 2230.15 (C?N). 1H NMR (400 MHz, DMSO-d6, 298 K): delta, ppm 7.88-7.69 (3H, benzene -CH), 6.64 (2H, thiophene -CH), 4.63-4.13 (5H, -CH and -CH2). 13C NMR (400 MHz, CDCl3, 298 K): delta, ppm 160.38, 141.00, 140.83, 135.87, 126.21, 118.72, 115.71, 115.35, 113.48, 103.10, 100.16, 71.49, 68.00, 64.77. GC-MS: m/z 298 [M]+. C15H10N2O3S (298.04): calcd. C 60.39, H 3.38, N 9.39; found C 60.37, H 3.37, N 9.40.

According to the analysis of related databases, 51762-67-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Karada?, Sebahattin; Bozo?lu, Ceyda; Kasim ?ener; Koca, Atif; Dyes and Pigments; vol. 100; 1; (2014); p. 168 – 176;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, 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. Product Details of 328-87-0

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C for 21/2 hours. The reaction mixture is cooled and poured into deionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

The synthetic route of 328-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US4063929; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts