Category: nitriles-buliding-blocks

Application of 53312-78-0,Some common heterocyclic compound, 53312-78-0, name is 3-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

Representative of synthesis of ( N-(3-(3-aminopropanamido)-5-chlorobenzyl)-6 – chloro-1, 3, 4,9-tetrahydro-2H-pyrido[ 3, 4-b lindole-2-carboxamide : To a solution of 3-amino-5- chlorobenzonitrile (1.0 g, 6.55 mmol,1.0 eq), 3-((tert-butoxycarbonyl) amino) propanoic acid (1.24 g, 6.55 mmol,1.0 eq) and HATU (2.98 g, 7.86 mmol,1.2 eq) in DMF (15 mL) was added DIEA (2.5 g,19.65 mmol, 3.0 eq) at 25 C. Then the reaction mixture was stirred at 25 C for 1 hr. TLC showed 3 -amino-5 -chlorobenzonitrile was consumed completely and one new spot formed. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined organic phase was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent: PE/EA = 5/1 to 3/1) to give tert-butyl (3 -((3- chloro-5-cyanophenyl) amino)-3-oxopropyl) carbamate (1.5 g, yield: 70.8%) as a yellow solid. NMR (400 MHz, DMSO-^) d 10.42 (s,1 H), 7.98 (d, J = 1.6 Hz,1 H), 7.92 (s,1H), 7.71 -7.67 (m,1 H), 6.90 (t, J = 5.2 Hz,1 H), 3.32 (s, 2 H), 3.22 (dd, J = 12.8, 6.8 Hz, 2 H),1.37 (s, 9 H). [0234] To a solution of tert-butyl (3-((3-chloro-5-cyanophenyl) amino)-3-oxopropyl) carbamate (500 mg,1.54 mmol,1.0 eq) in methanol (10.0 mL) was added Raney-Ni (180 mg, 3.08 mmol, 2.0 eq) and NH3·H20 (0.1 mL). The reaction was stirred at 25 C for 4 hrs under . LCMS showed the complete consumption of the starting material, and the desired product mass was detected. The reaction mixture was filtered and concentrated in vacuo to give tert-butyl (3- ((3-(aminomethyl)-5-chlorophenyl) amino)-3-oxopropyl) carbamate (460 mg, yield: 90.9%) as a yellow oil. LCMS: [M+H] + = 328.1

The synthetic route of 53312-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RECREO PHARMACEUTICALS LLC; ZHANG, Jing; WANG, Xiang; PODOLL, Jessica, D.; (207 pag.)WO2020/37155; (2020); A1;,
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3759-28-2, name is 2-(Cyanomethyl)benzonitrile, 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. COA of Formula: C9H6N2

General procedure: To a solution of homophthalonitrile 2 (129 mg, 0.82 mmol) in PriOH (4 ml), salicylaldehyde 1 (2.46 mmol) and NH4OAc (143 mg, 1.64 mmol) were added. The mixture was placed into a microwave reactor and heated at 150 C for 10 min. The vessel was opened, MeNO2 (0.439 ml, 8.2 mmol) and Et3N (0.114 ml, 0.82 mmol) were added, the mixture was heated again in the microwave reactor at 150 C for 10 min. The solvent was evaporated under reduced pressure, the residue was chromatographed on silica gel (EtOAc-hexane, 1:5-1:1) (method A) or was dissolved in asmall volume of Et2O or CH2Cl2 and extracted with HCl aqueous solution(0.6 m, 3 30 ml). The aqueous layer was neutralized with Na2CO3. The precipitate was filtered off and washed with H2O several times and once with a small amount (1.5 ml) of PriOH and dried in air (method B).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Festa, Alexey A.; Storozhenko, Olga A.; Bella Ndoutoume, Delphine R.; Varlamov, Alexey V.; Voskressensky, Leonid G.; Mendeleev Communications; vol. 27; 5; (2017); p. 451 – 453;,
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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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 20249-16-5

Step 2. 3-Hydroxycyclobutane-l-carbonitrile. Sodium borohydride (597 mg, 15.8 mmol) was added in portions into a cold (0 C) mixture of 3-oxocyclobutane-l- carbonitrile (1.0 g, 10.52 mmol) and anhydrous methanol (10 mL). After the addition the mixture stirred for 30 minutes, and then it was carefully poured into ice water. The mixture was extracted with ethyl acetate and the organic extracts washed with water and brine and dried over anhydrous MsS04. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes: EtOAc 2/1 ratio) to afford 3- hydroxycyclobutane-l-carbonitrile, 8: 1 isomeric mixture, as oil (920 mg, 92% yield): XH NMR (500MHz, CDCh) delta ppm [4.62 (m), 4.26 (m), 1H], [3.06 (m), 2.75 (m), 2H], [5.65 (m), 2.33 (m), 2H], 2.6 (m, 1), 2.31 (m, 1H).

The synthetic route of 20249-16-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 327-74-2, name is 2-Amino-5-cyanobenzotrifluoride, 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 327-74-2, Recommanded Product: 327-74-2

Intermediate I-IX-6 (I-19): 4-iodo-3-(trifluoromethyl)benzonitrile To a slurry of 4-amino-3-(trifluoromethyl)benzonitrile (5.48 g; 29.5 mmol) in HBF4 (50 mL; 48%) at -10 C. was added NaNO2 (2.24 g; 32.4 mmol), portionwise over 10 min. The mixture was stirred 30 min, precipitated solids were collected by filtration (Note 1) and (without delay) added portionwise to a solution of KI (7.84 g; 47.2 mmol) in acetone/water (50 mL of a 40% v/v solution). The mixture was decolorized by addition of 10 wt % Na2S2O3, precipitate was collected by filtration, washed with water and slurried in PhMe. The slurry was concentrated to dryness, affording the title compound as a pale orange solid, used without further purification. 1H NMR (400 MHz, DMSO-d6) delta 7.83 (dd, J=8.1, 1.6 Hz, 1H), 8.27 (d, J=1.5 Hz, 1H), 8.37 (d, J=8.1 Hz, 1H). Note 1 Solid was not allowed to dry completely on the filter.

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-Amino-5-cyanobenzotrifluoride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Smithkline Beecham Corporation; US2011/124559; (2011); A1;,
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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. 3598-14-9, name is Phenoxyacetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of Phenoxyacetonitrile

(a) 5 millimoles (0.665 g) of phenoxy-acetonitrile are dissolved in 8 ml of anhydrous toluene at 0 C., under an argon atmosphere 7.5 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (5 ml) are added dropwise, at this temperature. The stirring is maintained for 1 hour at 0 C., then 5.9 ml (1.3 eq) of diethylaluminum cyanide are added. The reaction mixture is stirred for 3 hours at room temperature, then hydrolyzed with 4 ml of methanol and pasty sodium sulfate. After purification by high pressure liquid chromatography on silica, there are obtained 0.182 g of 2-amino-3-phenoxy-propionitrile, in form of a cream-colored solid-state product; M.P. 65 C., yield: 22%.

The synthetic route of 3598-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Albert Rolland S.A.; US4942221; (1990); A;,
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Application of 41963-20-6,Some common heterocyclic compound, 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, molecular formula is C8H6BrN, 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 solution of 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (2007); A1;,
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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. 72291-30-6, name is Methyl 2-cyano-2-methylpropanoate, A new synthetic method of this compound is introduced below., COA of Formula: C6H9NO2

At -10C, hydrogen chloride gas was bubbled into an ethanol (50 ml) solution of 8.00 g of the mixture of cyano-dimethylacetic acid ethyl ester and cyano-dimethylacetic acid methyl ester (I-69), while stirring for 6 hours. After concentration of the reaction solution, ether was added to the thus obtained residue and stirred for 30 minutes, and the precipitated crystals were collected by filtration and dried to obtain 8.2 g of the title compound as a colorless solid. This was directly used in the subsequent reaction.

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; DAIICHI PHARMACEUTICAL CO., LTD.; EP1717238; (2006); A1;,
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Related Products of 94087-40-8, These common heterocyclic compound, 94087-40-8, name is 3-Chloro-2-fluorobenzonitrile, 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.

3L bottle take four reflux means of 2-fluoro-3-chlorobenzonitrile 437g, water 500g, concentrated sulfuric acid, 1248g, acetic acid 21g, slowly warmed to reflux and reflux temperature of about 155 , heat the reaction 5h, the control sample, the raw material ?1%, the reaction was stopped, cooled to 50 , dropping water 750g, stirred for 1h and then cooled to 10 , filtration, the filter cake with the amount of water rinsed, drained, dried was 458.5g, content ?99%, yield 93.5%.

The synthetic route of 94087-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Yongtai Technology Co ., Ltd; Zhang, xing; Shu, zhujin; (10 pag.)CN104529729; (2016); B;,
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Application 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: 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, Computed Properties of C7H5FN2

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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