Author: Jessica.F

Related Products of 21667-62-9, 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. 21667-62-9 name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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.

Step A; 3-Amino-l-(3-chloro-phenyl)-propan-l-ol; To a stirred suspension of LAH (16 g, 90 mmol) in dry THF (200 mL) was added a solution of 3-(3-chlorophenyl)-3-oxopropanenitrile (10.4 g, 270 mmol) in dry THF (200 mL) dropwise at 0 C under nitrogen atmosphere. The mixture was warmed to 25 C and then heated at 60 C for 3 hours. After cooling to 0 C, a saturated solution of sodium hydroxide was added dropwise and extracted with ethyl acetate (200 mL). The solution was dried over anhydrous sodium sulfate and concentrated to dryness. The crude 3-amino-l-(3-chloro-phenyl)-propan-l-ol obtained was used in the next step without further purification. (Yield 14.5 g, crude).LC-MS: [M+H]+ 186.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LIU, Wenjian; LUK, Kin-Chun Thomas; ZHANG, Xiaohu; WO2012/98068; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 38487-86-4, These common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, 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.

[00716] To a solution of compound 239-1 (1.3 g, 8.5 mmol, 1.0 eq) and [4-(trifluoromethyl)phenyl]boronic acid (2.43 g, 12.8 mmol, 1.5 eq) in DCM (20 mL) was added DIPEA (2.20 g, 17 mmol, 3 mL, 2.0 eq) and Cu(OAc)2 (2.32 g, 12.78 mmol, 1.5 eq) under N2. The suspension was degassed under vacuum and purged with 02 several times. The mixture was stirred under 02 (15 psi) at 25 C for 18 hours. TLC (Petroleum ether/ethyl acetate = 5/1, UV) indicated that the staring material was remained and two new spots were formed. LCMS showed that 16% of desired mass was detected. The reaction mixture was filtered and the filter was concentrated in vacuum. The residue was purified by column chromatography (Si02). Compound 239-2 (330 mg, 1.1 1 mmol, 13% yield) was obtained. 1HNMR (400 MHz, CDC13) 7.64 (d, J = 8.52 Hz, 2H), 7.49 (d, J= 8.52 Hz, 1H), 7.26 – 7.29 (m, 3H), 6.94 (dd, J = 8.42, 1.88 Hz, 1H), 6.55 (s, 1H).

Statistics shows that 2-Amino-4-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 38487-86-4.

Reference:
Patent; VIVACE THERAPEUTICS, INC.; KONRADI, Andrei W.; LIN, Tracy Tzu-Ling Tang; (396 pag.)WO2018/204532; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1813-33-8,Some common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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 mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
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Reference of 63069-50-1, 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. 63069-50-1 name is 4-Amino-3-fluorobenzonitrile, 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 a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

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; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); 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. 3598-13-8, name is 2-(4-Chlorophenoxy)acetonitrile, A new synthetic method of this compound is introduced below., name: 2-(4-Chlorophenoxy)acetonitrile

Intermediate 2; 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one; Step 1: (5-methoxy-2-nitrophenyl)-acetonitrile; 24.0 g (214 mmol) potassium-tert-butoxide in 100 mL DMF were slowly added dropwise to a solution of 13.2 g (86.0 mmol) 4-nitroanisole and 18.0 g (107 mmol) of 4-chlorophenoxy-acetonitrile in 50 mL DMF. The reaction mixture was stirred for 30 min at -10 C. and then poured into 300 g of a 1:1 mixture of conc. HCl and ice. After extraction with EtOAc the organic phase was washed with water, dried and evaporated down i. vac. The residue was treated with a 1:1 mixture PE/EtOAc and the product that crystallised out was suction filtered. After washing with a 1:1 mixture of petroleum ether/EtOAc the crystals were dried in the air.Yield: 6.5 g (39% of theoretical)ESI-MS: m/z=210 (M+NH4)+ Rf: 0.45 (silica gel; PE/EtOAc=1:1)

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/324028; (2010); 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 654-70-6

Synthesis of (2R)-3-Bromo-N-[4-cyano-3-(trifluoromethyl) phenyl]-2-hydroxy-2- methylpropanamide. Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4 C) of 6 (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2- cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at room temperature. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, extracted with EtOAc (2 X 400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2 X 300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2ZEtOAc (80:20) to give a solid. This solid was recrystallized from CH2Cl2/hexane to give 55.8 g (73.9%) of (2R)-3- Bromo-N-[4-cyano-3-(trifluoromethyl) phenyl] -2-hydroxy-2-methylpropanamide as a light- yellow solid. 1H NMR (CDC13/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1eta, OH), 3.63 (d, / = 10.8 Hz, IH, CH2), 4.05 (d, / = 10.8 Hz, IH, CH2J, 7.85 (d, / = 8.4 Hz, IH, ArH), 7.99 (dd, / = 2.1, 8.4 Hz, IH, ArH), 8.12 (d, / = 2.1 Hz, IH, ArH), 9.04 (bs, 1eta, NH). Calculated Mass: 349.99, [M-H]- 349.0. M.p.: 124-126 0C.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; AHN, Tai; WO2009/36206; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 51762-67-5, 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. 51762-67-5 name is 3-Nitrophthalonitrile, 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.

The compounds 4-hydroxy-3-methoxybenzoic acid (0.97g, 5.78mmol) and 3-nitrophthalonitrile (1.0g, 5.78mmol) were dissolved in dry DMF (30ml) and anhydrous K2CO3 (1.59g, 11.56mmol) was added in portions over 2h. After stirring for 4 days at 50-60C, the reaction mixture was treated with diluted HCl under ice cooling. The pure precipitate that formed was filtered, washed with water to neutralize and dried. Yield: 1.15g (68%). M.p. 238-240C. Anal. Calc. for C16H10N2O4: C, 65.31; H, 3.43; N, 9.52; O, 21.75. Found: C, 65.20; H, 9.19; N, 3.23; O, 21.58%. FT-IR (KBr), numax/(cm-1): 3084 (Ar-CH), 2921-2851 (aliphatic CH), 2231 (C?N), 1675 (C=O), 1574-1458 (C=C), 1277 (Ar-O-Ar), 1247, 1182, 983, 756, 650, 509, 456. 1H NMR (d-DMSO 500MHz, delta ppm): 7.81 (dd, 1H, Ar-H), 7.76 (t, 1H, Ar-H), 7.49 (dd, 1H, Ar-H), 7.12 (dd, 1H, Ar-H), 7.64 (dd, 1H, Ar-H), 7.69 (s, 1H, Ar-H), 3.79 (s, 3H, OCH3). UV-Vis lambdamax (nm) (log epsilon) in DMSO: 297 (4.35).

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

Reference:
Article; Oezguel, Gamze; Ta?temel, Ay?eguel; Oezkaya, Ali Riza; Bulut, Mustafa; Polyhedron; vol. 85; (2015); p. 181 – 189;,
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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. 14447-18-8, name is Benzyl cyanoacetate, A new synthetic method of this compound is introduced below., Quality Control of Benzyl cyanoacetate

A stirred mixture of naltrexone (1.70 g; 5.0 mmol), benzyl cyanoacetate (1.31 g; 7.5 mmol) and sulfur (0.24 g; 7.5 mmol) in DMF (15 mL) was treated dropwise at room temperature with morpholine (0.66 mL; 7.6 mmol) and the mixture was then heated under reflux at 80 C. for 24 h. The reaction mixture was allowed to cool to room temperature and poured over ice-water mixture. The solid obtained was collected by filtration, washed with water and dried. The crude product was purified by flash chromatography over a column of silica using CHCl3-MeOH (99:1) as the eluent to obtain 8d (1.16 g): mp 208-212 C. dec; TLC, Rf 0.69 (CHCl3-MeOH 9:1).

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; Southern Research Institute; US2006/47119; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 25808-30-4, 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension ofcompound 18 (147 mg, 0.67 mmol) in1,2-dichloroethane (8 mL), methylaminoacetonitrile hydrochloride (79mg, 0.74 mmol) was added at room temperature. After 5 min, DIPEA (130 muL, 0.74mmol) was added, followed by the slow addition of Na(OAc)3BH (185mg, 0.87 mmol). The reaction mixture was then heated to 70 °C and left to stirat that temperature for 24 h. Then, CH2Cl2 (10 mL) wasadded and the mixture extracted with saturated aqueous solution of NaHCO3(20 mL). The aqueous phase was further washed with CH2Cl2(2× 50 mL), the combined organic layers were dried with anhydrous Na2SO4,filtered, and evaporated under reduced pressure. The crude product was purifiedby flash column chromatography using CH2Cl2/MeOH/NH4OH= 10/1/0.1 as an eluent, to yield 80 mg (44percent) of yellow solid. Mp 116.0?117.0 °C;Rf = 0.23 (CH2Cl2/MeOH/NH4OH= 3/1/0.1); 1H NMR (400 MHz, DMSO-d6) delta 2.32 (s, 3H, CH3),3.87 (s, 2H, CH2CN), 3.95(s, 2H, CH2N), 7.17 (d, J = 8.9 Hz, 1H, Ar-H), 7.89 (d, J = 9.0 Hz,1H, Ar-H), 8.50 (d, J = 8.9 Hz, 1H, Ar-H), 9.13 (d, J = 9.0 Hz,1H, Ar-H), 11.28 (br s, 1H, OH);1H NMR (400 MHz, CDCl3) delta 2.51 (s, 3H, CH3), 3.60 (s, 2H, CH2CN),4.00 (s, 2H, CH2N), 7.22(d, J = 8.8 Hz, 1H, Ar-H), 7.88 (d, J = 8.9 Hz, 1H, Ar-H),8.59 (d, J = 8.8 Hz, 1H, Ar-H), 9.34 (d, J = 8.9 Hz, 1H, Ar-H),resonance for OH missing; 13C NMR (100 MHz, DMSO-d6) delta 41.35, 44.98, 61.32, 110.07, 115.81, 121.69,124.56, 128.52, 132.92, 135.16, 136.70, 157.79, 160.34; HRMS (ESI) m/z calculated for C11H13N4O3 [M+H]+ 273.0988, found 273.0986; HPLC purity, 95.51percent, tR = 8.66 min.

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

Reference:
Article; Sosi?, Izidor; Mitrovi?, Ana; ?uri?, Hrvoje; Knez, Damijan; Brodnik ?ugelj, Helena; ?tefane, Bogdan; Kos, Janko; Gobec, Stanislav; Bioorganic and Medicinal Chemistry Letters; vol. 28; 7; (2018); p. 1239 – 1247;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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 50397-74-5, Computed Properties of C7H5BrN2

To a mixture of 4-amino-3-bromobenzonitrile (10.0 g, 0.050 mmol) and methyl acrylate (9.19mL, 0.101 mmol) in acetonitrile (200 mL) was added palladium acetate (0.568 g, 0.0025mmol) and tri-o-tolyl phosphine (1.54 g, 0.005 mmol) and Et3N (14.64 mL, 0.105 mmol). The reaction mixture was heated to reflux for 48 h. The reaction mass was filteredthrough celite and washed the bed with ethyl acetate. The filtrate was concentrated to afford 6.0 g of title product. ?H NMR (300 MHz, DMSO-d6): 7.92 (s, 1H), 7.82-7.77 (d, J = 15.6Hz, 1H), 7.4 1-7.38 (d, J = 8.7 Hz, 1H), 6.77-6.74(d, J = 8.7 Hz, 1H), 6.64 (s, 2H), 6.56-6.5 1 (d, J= 15.6 Hz, 1H), 3.70 (s, 3H).

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; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts