Tag: M.W=100-200

Synthetic Route of 796600-15-2, A common heterocyclic compound, 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, molecular formula is C8H5ClFN, 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.

Examples 11 and 12Example 11 Example 12 11a to l ib(R)-2-(3 -chloro-4-cyano-2-methylphenylamino)-3 -hydroxypropanoic acidTo a stirred solution of 2-chloro-4-fluoro-3-methylbenzonitrile (1 la) (1.0 gm, 5.8 mmol) in DMSO (10 mL), D-Serine (1.4 gm, 13.3 mmol) was added followed by K2C03 (1.7 gm, 12.3 mmol) at room temperature. The resulting reaction mixture was heated to 90C for 12 h. After completion of reaction (by TLC), the reaction mixture was poured into ice-cold water (300 mL) and extracted with EtOAc (100 mL). The aqueous layer was acidified with citric acid (pH ~3) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over Na2S04, and concentrated under reduced pressure to afford the acid 1 lb (0.3 gm, crude) as off- white solid. The crude material was taken for the next step without purification.TLC: 10% MeOH/DCM (Rf: 0.2)1H NMR (500MHz, DMSO-c¾, delta in ppm): 8.2-10.2 (br s, 1H), 7.54 (d, J= 8.5 Hz, 1H), 6.57 (d, J= 9.0 Hz, 1H), 5.79 (d, J= 7.5 Hz, 1H), 4.20 (t, J= 3.0 Hz, 1H), 3.86-3.79 (m, 2H), 3.22 (br s, 1H), 2.25 (s, 3H).

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; RADIUS HEALTH, INC.; MILLER, Chris, P.; WO2012/47617; (2012); A1;,
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Synthetic Route of 10406-24-3, 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. 10406-24-3, name is 3-(Aminomethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2 m-Cyanobenzylamine (13.2 g), sodium nitrite (10.4 g), and dimethylformamide (100 ml) were mixed together, and the mixture was vigorously stirred at room temperature. Trifluoroacetic acid (22.8 g) was added dropwise to the mixture over one hour. After completion of addition, the mixture was further allowed to react at 100 C. for one hour. For the subsequent process, the procedure of Example 1 was repeated, to thereby obtain 6.9 g of m-cyanobenzyl alcohol (bp. 128-130 C./400 Pa) (yield 52%). The purity of the product was 98%.

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-(Aminomethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Showa Denko K.K.; US6187945; (2001); B1;,
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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 1194-02-1 as follows. category: nitriles-buliding-blocks

To a solution of 4-fluorobenzonitrile (0.500 g, 4.13 mmol) in ethanol (3 mL) was added hydroxyl amine HCl (0.427g, 6.19 mmol) and potassium carbonate (1.14g, 8.26 mmol). The reaction mass was stirred at RT for 15-17 h. Excess of solvent was removed under vacuum. The obtained residue was diluted with water, acidified with dilute HCl and extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.450 g of desired product. 1H NMR (300 MHz, DMSO d6): delta 5.84 (br s, 2H), 7.17-7.27 (m, 2H), 7.68-7.73 (m, 2H), 9.64 (br s, 1H); MS (m/z): 155.13 (M+H)+.

According to the analysis of related databases, 1194-02-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2013/186692; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, 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 63069-50-1, Product Details of 63069-50-1

3.123. Compound 111: (lR,2R)-N-[6-(2-chloro-4-cyano-6-fluoro-N-methyl-anilino)-l-methyl- 3.123.1. Step i): 4-amino-3-chloro-5-fluoro-benzonitrile A mixture of 4-amino-3-fluorobenzonitrile (184 mmol) and NCS (276 mmol) in AcOH (300 mL) is stirred at 70C for approximately 16 h. The mixture is concentrated. H20 is added to the residue and the solid product is filtered off and washed (sat. NaHCC>3 and H20). To eliminate H20, THF is added and removed under reduced pressure to yield the desired product (Int. 21). 3.123.2. Step ii): 4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2- pyridyl]amino]-3-chloro-5-fluoro-benzonitrtte

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
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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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17417-09-3

Part A Preparation of 2-fluoro-5-aminobenzonitrile To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride (27.0 g, 120 mmol). The reaction mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water (5*75 mL), brine (75 mL); dried over sodium sulfate (anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

According to the analysis of related databases, 17417-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DuPont Pharmaceuticals Company; US6020357; (2000); A;,
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Electric Literature of 77326-36-4, 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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under argon, 2-amino-6-fluorobenzonitrile (300 mg, 2.20 mmol) was dissolved in pyridine (3.6 ml, 44 mmol), 4-dimethylaminopyridine (2.69 mg, 22.0 muiotaetaomicron) and 3-Chlorobenzoylchlorid (501 mg, 2.86 mmol) were added and the mixture was stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate, washed with water and brine, and dried over magnesium sulfate. Concentration in vacuo and purification by preparative HPLC afforded the title compound. The obtained amount was 401 mg (100% Purity, 66 % of theory). LC-MS (Method 1): Rt = 0.97 min; MS (ESIPos): m/z = 275 [M+H]+

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUSS, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; (308 pag.)WO2016/173948; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 34662-24-3, name is 2-Chloro-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 34662-24-3, COA of Formula: C7H3ClN2O2

A solution of anhydrous EtOH (20 mL) was bubbled through NH3 at 0C to obtain 7M NH3/EtOH. It was transfered intoa sealed tube containing 2-chloro-3-nitrobenzonitrile (0.5 g, 2.7 mmol, 1.0 eq). The mixture was allowed to warm to 18C gradually and then stirred at 110C for 12 hours. The mixture was evaporated under reduced pressure to remove the most solvent to give 0.5 g of crude 2- amino-3-nitrobenzonitrile as a yellow solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
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Application of 17417-09-3, 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 17417-09-3 as follows.

Part A Preparation of 2-fluoro-5-aminobenzonitrile To a solution of 2-fluoro-5-nitrobenzonitrile (2.0 g, 12 mmol) in ethyl acetate(50 mL) was added stannous chloride (27.0 g, 120 mmol). The reaction mixture was stirred at reflux 1.5 h, then cooled to room temperature. Partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate(150 mL). Organic phase was separated and washed with water (5*75 mL), brine (75 mL); dried over sodium sulfate (anhy.); filtered and concentrated to give 2-fluoro-5-aminobenzonitrile (1.4 g) as pure compound.

According to the analysis of related databases, 17417-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DuPont Pharmaceuticals Company; US6020357; (2000); 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. 51762-67-5, name is 3-Nitrophthalonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

The phthalonitrile compund ( 5) was synthesized by the reaction between 5-Methyl-1,3,4-thiadiazole-2-thiol (1) and 3-nitrophthalonitrile (3) in dry DMF in the presence of K2CO3 according to literature [25].

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; Demirba?, Uemit; Pi?kin, Mehmet; Bayrak, R?za; Durmu?, Mahmut; Kantekin; Journal of Molecular Structure; vol. 1197; (2019); p. 594 – 602;,
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Synthetic Route of 3544-25-0, These common heterocyclic compound, 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, 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.

(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 x 25 cm, CH2CI2/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. ‘H-NMR (400 MHz, DMSO-d6) : 9.82 (s, 1 H, 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).

The synthetic route of 3544-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts