Month: August 2021

Synthetic Route of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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.

N-(4-Cyano-2-methoxyphenyl)formamide Acetic anhydride (0.65 mL, 6.7mmol) was cooled in an ice bath and formic acid (0.38 mL, 10 mmol) was added with stirring. The ice-bath was removed and the mixture was stirred for a further 60 minutes. The reaction was re-cooled in the ice-bath and 4- amino-3-methoxybenzonitrile (0.25 g, 1.58 mmol) was added. The reaction was stirred at ice-bath temperature for 5 minutes, then at room temperature for 60 minutes. The reaction was concentrated in vacuo, azeotroped with toluene and the title compound was precipitated from ether/hexanes as a white powder (255 mg, 71.3%). 1 H NMR (500 MHz, DMSO-d6): delta 10.07 (s, 1 H), 8.39 (s, 1 H), 8.37 (s, 1 H), 7.52 (d, J = 1.7 Hz, 1 H), 7.4 (dd, J = 8.4, 1 .8 Hz, 1 H), 3.92 (s, 3H). LCMS (ESI) R, = 1 .76 minutes MS m/z 177 [M+H]+

The synthetic route of 177476-76-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; HOELDER, Swen; BLAGG, Julian; CHEUNG, Jack; ATRASH, Butrus; SHELDRAKE, Peter; WO2014/37751; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 103146-25-4, Quality Control of 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

A, To 40g citalopram diol intermediate free alkali crystal prepared in Example 1 (purity: 99.9%, HPLC, area normalization method), 360ml isopropanol was added and the solution was heated until the crystal was dissolved entirely. 23.6g D-di-4-methylbenzyol tartaric acid was added and dissolved, the solution was placed at room temperature for 12 hours. The crystal crystallized and was filtrated, washed with small amount of isopropanol to give S-citalopram diol intermediate—D-di-4-methylbenzyol tartaric acid salt crystal. The obtained salt was then suspended and mixed in toluene, added with NaOH solution and stirred. The solution was placed aside, the organic and inorganic layer was separated. The toluene layer was heated, concentrated under vacuum to give 14g S-citalopram diol intermediate oil substance (yield: 70%, purity: 99.9%), in which there was 0.5% R-citalopram diol intermediate (chiral HPLC).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Hangzhou Minsheng Pharm. Co., Ltd.; EP1700851; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 6330-25-2, 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. 6330-25-2, name is 2-Cyano-N-methyl-acetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1.12 g (28.06 mmol) of sodium hydride at 60% in mineral oil are added, fractionwise, to a solution, cooled to 0-5 C., of 1.31 g (13.36 mmol) of N-methylcyanoacetamide (prepared according to 1.3) in 20 ml of anhydrous dimethylformamide. Stirring is continued at this temperature for ten minutes and then a solution of 3.55 g (4.93 mmol) of 6-chloro-2-[(pyridin-2-ylmethyl)amino]nicotinoyl fluoride in 20 ml of dimethylformamide is added. The medium is stirred overnight at ambient temperature and then 0.561 g (14.03 mmol) of sodium hydride at 60% is added fractionwise. Stirring is continued at this temperature for 1 hour minutes, and then the reaction mixture is poured onto ice and the subsequent mixture is acidified to pH 5-6 with an aqueous solution of acetic acid at 10%. The precipitate is isolated by filtration and, after drying in an oven, 3.98 g of the expected product are obtained in the form of a beige solid. MH+=344. Yield=87%. 1H NMR (DMSO-d6, 400 MHz, delta in ppm): delta 9.20 (s, <1H, very broad); 8.85 (s, 1H); 8.30 (m, 1H); 8.10-7.85 (m, 2H, broad); 7.80 (d, 1H); 7.75 (s, 1H, broad); 6.90 (d, 1H); 4.90 (s, 2H); 2.95 (s, 3H). 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-Cyano-N-methyl-acetamide, other downstream synthetic routes, hurry up and to see. Reference:
Patent; SANOFI-AVENTIS; US2010/144757; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 25808-30-4,Some common heterocyclic compound, 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, molecular formula is C3H7ClN2, 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 1 To a solution of 3-(4-fluorobenzoyl)-2-pyridinecarboxylic acid (19.8 g) in dichloromethane (200 ml) were added thionyl chloride (29.1 ml) and DMF (one drop). The mixture was stirred for 4 hours at room temperature. The solvent was distilled off, and the residue was dissolved in dichloromethane (100 ml). This solution was added to a mixture of N-methylaminoacetonitrile hydrochloride (9.46 g), triethylamine (33.7 ml) and dichloromethane (150 ml), which was stirred for 16 hours at room temperature. The solvent was distilled off. To the residue was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with an aqueous solution of sodium hydrogencarbonate and water, which was then dried, followed by distilling off the solvent to leave N-cyanomethyl-3-(4-fluorobenzoyl)-N-methyl-2-pyridinecarboxamide (22.8 g). NMR(200 MHz,CDCl3) ppm: 3.16(3H*1/3,s), 3.21(3H*2/3,s), 4.44(2H*2/3,s), 4.55(2H*1/3,s), 7.17(2H,t,J=8.4 Hz), 7.50(1H,m), 7.85(3H,m), 8.75(1H,dd,J=1.6,4.8 Hz)

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5585385; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 499983-13-0, The chemical industry reduces the impact on the environment during synthesis 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 3-fluoro-4-bromophenylacetonitrile (2g, 9.2mmol) and 1,2-dibromoethane (0.6ml, 7mmol) in toluene (5ml) was added 50% NaOH (5mL) and TBAB (0.32g , 1 mmol). The mixture was stirred vigorously at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate.The organic solution was washed with 1N HCl and then with brine, dried over anhydrous sodium sulfate and concentrated.Separation by column chromatography (eluent: PE / EA = 20/1, v / v), a yellow solid was obtained with a yield of 91%.

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-Bromo-3-fluorophenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; China Pharmaceutical University; Sun Haopeng; He Siyu; Liu Yang; (25 pag.)CN110590548; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, 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 103146-25-4, Product Details of 103146-25-4

Oxalate [(+-)-Diol Oxalate Salt] (+-)-Diol compound (VI) (360 g, 1.05 mol) was dissolved in ethanol (1400 ml) and heated to 50-55 C. to obtain a clear solution. Oxalic acid dihydrate (164.40 g, 1.3 mol) was added slowly and cooled the obtained solution to 15-20 C. and stirred for 4 hrs to complete the crystallization. Product formed was filtered and dried at 50-60 C. under vacuum to yield 360 g of Diol oxalate salt (VIa), with HPLC purity of 99.95%. (Melting Range: 168-171 C.) 1H NMR (DMSO-d6) delta ppm: 7.89-7.09 (m, 7H), 5.54 (d. 1H), 4.03 (d, 1H), 2.98-2.94 (m, 2H), 2.63 (s, 6H), 2.32-2.15 m, 2H), 1.6-1.3 (m, 2H) IR (KBr, cm-1):

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Kaushik, Vipin Kumar; Mohammed, Umar Khan; Meenakshisunderam, Sivakumaran; US2009/99375; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 630-18-2, 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. 630-18-2 name is Pivalonitrile, 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.

General procedure: To an ice cold solution of pivalonitrile (1f, 120 muL, 1.085 mmol) in Et2O (1.0 mL)was added an ethereal solution of 2-naphthylmagnesium bromide (2b, 0.75 M, 1.88mL, 1.410 mmol) and the reaction mixture was stirred at 60 C in a sealed tube for 2 h.After cooling to 0 C, the reaction mixture was treated with anhydrous MeOH (132muL), followed by the addition of CuBr2 (24.3 mg, 0.109 mmol) and anhydrous DMF(10.0 mL). The resulting reaction mixture was stirred at 80 C under an oxygenatmosphere for 6 h. Then the reaction was quenched by the addition of pH 9ammonium buffer solution and the organic materials were extracted with Et2O. Thecombined organic extracts were washed with water, and then with brine and driedover anhydrous MgSO4. The solvents were removed in vacuo and the resulting crudematerial was purified by flash column chromatography using hexane-EtOAc (90:10)to afford 2-naphthonitrile

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

Reference:
Article; Tnay, Ya Lin; Ang, Gim Yean; Chiba, Shunsuke; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1933 – 1943;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 17417-09-3, 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. 17417-09-3 name is 2-Fluoro-5-nitrobenzonitrile, 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.

2-Morpholin-4-yl-5-nitro-benzonitrile 3-Cyano-4-fluoronitrobenzene (3.3 g, 19.9 mmol) was dissolved in ethyl acetate (10 mL). Morpholine (2.2 mL, 25 mmol), and N,N-diisopropylethylamine (3.5 mL, 20 mmol) were added and the mixture stirred overnight at room temperature. At 17 h, additional ethyl acetate (150 mL) was added and the combined mixture was washed with water (50 mL) and brine (50 mL), dried (Na2SO4), filtered and concentrated under vacuum. The residue was used without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/87575; (2004); A1;; ; Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. category: nitriles-buliding-blocks

To a stirred solution of 2-bromo-5-chlorobenzonitrile (80 g, 370 mmol) in THF (1000 mL)at 0C was added EtMgBr (370 mL, 1110 mmol) dropwise. The reaction mixture wasstuffed at 0-5C for 5 hours before MeOH (500 mL) was added dropwise. After the solution was stuffed for another 15 mi NaBH4 (28 g, 740 mmol) was added carefully and the resulting mixture was stirred at room temperature for 16 hours. The reaction solution was then poured into water and exacted with EtOAc (3 x). The combined organic layerswere dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by column chromatography (petroleum ether: EtOAc =3: 1) to afford the title compound (30 g, 34.6%) as yellowish oil. MS: 235.5 [M+Hj.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-37-0, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191338; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 1247885-40-0,Some common heterocyclic compound, 1247885-40-0, name is 2,3-Difluoro-5-nitrobenzonitrile, molecular formula is C7H2F2N2O2, 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.

5-amino-2,3-difluorobenzonitrile (0273) To a solution of 2,3-difluoro-5-nitrobenzonitrile (920 mg, 5.00 mmol) in acetonitrile (25 mL) was added iron powder (1.96 g, 35.10 mmol) and acetic acid (6.0 g, 99.91 mmol). The resulting mixture was stirred for 2 h at room temperature and the solid that formed in the reaction mixture were removed by filtration. The filtrate was diluted with water (100 mL) and the pH value of the mixture was adjusted to 8 with saturated sodium bicarbonate solution. The resulting mixture was extracted with ethyl acetate (150 mL×2) and the organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by a neutral alumina column with ethyl acetate in hexane (0% to 65% gradient) to yield 5-amino-2,3-difluorobenzonitrile as yellow solid (660 mg, 86%).

The synthetic route of 1247885-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts