Category: nitriles-buliding-blocks

Reference of 906673-45-8, A common heterocyclic compound, 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, molecular formula is C14H10BrNO2, 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.

In a three-necked flask, compound II (1.9 g), tetrahydrofuran (57 mL), triisopropyl borate (1.53 g) were added to cool down to -78C, and butyllithium (6.25 mL, 2.5 M concentration) was added dropwise.After completion of the reaction for 30 minutes or more, after completion of the reaction, 1N hydrochloric acid (57 mL) was added to quench the reaction, stirred for 30 minutes or more, and allowed to stand for stratification.The organic phase was concentrated under reduced pressure until no solvent was evaporated. Methanol (20 mL) was added to the obtained oil, concentrated hydrochloric acid (0.5 mL) was stirred at room temperature overnight, and after completion of the reaction, the mixture was concentrated under reduced pressure to obtain the target compound I (about 1.8 g).

The synthetic route of 906673-45-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yaoyuan Pharmaceutical Chemical (Shanghai) Co., Ltd.; Wang Yuan; Liu Chuanjun; Tang Wensheng; He Xungui; (8 pag.)CN107759625; (2018); A;,
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Synthetic Route of 3100-67-2, A common heterocyclic compound, 3100-67-2, name is 1-Amino-2-naphthonitrile, molecular formula is C11H8N2, 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.

The dried 1 L reactor was charged with nitrogen and then 50.0 g (297 mmol) of intermediate 13-a,500 mL of dimethylformamide is stirred.55.56 g (312 mmol) of N-bromosuccinimide are slowly added to the reactor.Stir at room temperature for 4 hours.When the reaction was completed, distilled water was added dropwise at room temperature to precipitate brown crystals. The crystals were separated by filtration and separated by column chromatography to obtain 68 g of intermediate 13-b.(Yield: 93%)

The synthetic route of 3100-67-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Ltd.; Choi Yeong-tae; Lee Se-jin; Park Seok-bae; Ryu Tae-jeong; Yang Byeong-seon; Lee Da-jeong; (92 pag.)KR2018/10087; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 362527-61-5, name is Ethyl 3-bromo-4-cyanobenzoate, 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 362527-61-5, Recommanded Product: 362527-61-5

EXAMPLE 206A 3-bromo-4-cyanobenzoic acid A solution of Example 87C (150 mg) in methanol (3 mL) and water (1 mL) was treated with LiOH (80 mg) and stirred for 2 hours. The solution was adjusted to pH 2 with 1M HCl, then extracted with ethyl acetate. The extract was dried (MgSO4), filtered, and concentrated to provide the desired product of sufficient purity for subsequent use without further purification. MS (DCI/NH3) m/z 243 and 245 (M+NH4)+; 1H NMR (300 MHz, CDCl3) delta 8.40 (d, 1H), 8.13 (dd, 1H), 7.79 (d, 1H).

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Reference:
Patent; Wang, Wei-Bo; Curtin, Michael L.; Fakhoury, Stephen A.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Hutchins, Charles W.; Li, Qun; Lin, Nan-Horng; Nelson, Lissa Taka Jennings; O’Connor, Steve; Sham, Hing L.; Sullivan, Gerard M.; Wang, Gary T.; Wang, Xilu; US2002/19527; (2002); A1;,
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Reference of 110-67-8, 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. 110-67-8, name is 3-Methoxypropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

methyl cyanoacetate9 bar of O2 were injected into a solution of 3.0 g (0.035 mol) of 3-methoxypropionitrile (Fluka), 0.5 g (3.0 mmol) of NHPI (N-hydroxy-phthalimide) and 57 mg (0.23mmol) of Co(CH3COO)2.4H2O in 50 ml of acetic acid in a pressure autoclave. The mixture was subsequently stirred at 150 C. for 5 h.

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-Methoxypropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lonza AG; US6700010; (2004); B1;,
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These common heterocyclic compound, 28442-78-6, name is 2-Chloroisophthalonitrile, 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. Quality Control of 2-Chloroisophthalonitrile

EXAMPLE 55A 3-Amino-2-carbomethoxy-7-cyano-benzthiophene 2-chloro-1,3-dicyanobenzene (972 mg, 6.0 mmol) was treated with 1 eq of methyl thioglycolate and 1 eq sodium carbonate in methanol as described in Example 41A to give the title compound in 65% yield. 1H NMR (300 MHz, D6-DMSO d 3.83 (s, 3H), 7.38 (bs, 2H), 7.62 (t, J=8 Hz, 1H), 8.10 (d, J=8 Hz, 1H), 8.50 (d, J=8 Hz, 1H). MS (DCI/NH3) m/e 250 (M+NH4)+.

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

Reference:
Patent; Abbott Laboratories; US5597823; (1997); A;,
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10444-38-9, name is Ethyl 4-cyanobutanoate, 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: C7H11NO2

General procedure: A 1 M solution of LiHMDS in THF (5.1 eq) was added slowly to a solution of NH2OBn.HCl (1.1 eq.) in THF (4 mL/mmol) at -78C. The mixture was stirred 30 min before the addition of the nitrile (1 eq). After total consumption of the starting materials (TLC), the reaction was quenched with a saturated aqueous solution of NH4Cl, warmed up to room temperature, and extracted three times with AcOEt. The collected organic layers were dried over Na2SO4, filtered and evaporated to dryness under reduced pressure.

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nguyen-Trung, Anh Thu; Tritsch, Denis; Grosdemange-Billiard, Catherine; Rohmer, Michel; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1643 – 1647;,
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Adding a certain compound to certain chemical reactions, such as: 406719-76-4, name is Methyl 4-cyano-2-methoxybenzoate, 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 406719-76-4, Application In Synthesis of Methyl 4-cyano-2-methoxybenzoate

A mixture of 4-cyano-2-methoxy-benzoic acid methyl ester (1.01 g, 5.28 mmol) in methanol (50 mL) was added to Raney-nickel 2800 slurry in water (a few grams washed with methanol to remove the water, Aldrich) and it was put under a 50 psi hydrogen atmosphere for 16 hrs. The mixture was filtered through Celite under an argon atmosphere and concentrated and then purified by flash chromatography to give 4-aminomethyl-2-methoxy-benzoic acid methyl ester (385.7 mg, 34.7%).

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, Methyl 4-cyano-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Liu, Jin-Jun; Morgan Ross, Tina; Zhang, Zhuming; US2011/86854; (2011); A1;,
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Application of 916792-09-1,Some common heterocyclic compound, 916792-09-1, name is 2-Bromo-4-fluoro-6-methylbenzonitrile, molecular formula is C8H5BrFN, 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.

2-Bromo-4-fluoro-6-methyl-benzonitrile (IX) (0.428 g, 2 mmol) was heated in 70% aqueous sulfuric acid (2 mL)overnight at 150 00 The reaction mixture was poured into ice and extracted with ethyl acetate (4 x 2 mL). The organic phase was washed with water (4 x 2 mL), brine (2 x 2 mL), dried over Na2SO4, filtered and concentrated to give 300 mg of crude 2-bromo-4-fluoro-6-methyl-benzamide (VIII). Pure sample was obtained by recrystallization from benzene. 1H NMR (400.5 MHz, DMSO-d6) ppm 3.31 (s, 3H), 7.17 (dd, JH-F = 9.8 Hz, JH-H 2.2 Hz, 1H), 7.41 (dd, JH-F 8.6Hz, JH-H = 2.2 Hz, 1H), 7.89 (br. s, 1H), 7.65 (br. s, 1H).

The synthetic route of 916792-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; PAPEO, Gianluca Mariano Enrico; KRASAVIN, Mikhail Yurievitch; ORSINI, Paolo; SCOLARO, Alessandra; WO2014/64149; (2014); A1;,
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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. 6283-71-2, name is Dimethyl 2-cyanosuccinate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Dimethyl 2-cyanosuccinate

Preparation 100; 1- [2, 6-dichloro-4-pentafluorothiophenyl]-5-hydroxy-1 H-pyrazole-3-carbonitrile; Sodium nitrite (1.32 g, 19.1 mmol) was added carefully to sulphuric acid (concentrated, 6.8 ml), whilst cooling the solution to 0°C. The solution was heated to 60°C for 30 min, allowed to cool and then diluted with acetic acid (12 ml). To the solution was added 2, 6-dichloro-4-pentafluorothiophenylamine (WO 9421606 A1, 5.0 mg, 17.4 mmol) in acetic acid (11 ml) and the reaction mixture was heated at 55°C for 1 h. To a solution of dimethyl 2-cyanosuccinate (Hall, H. K. , Jr.; Ykman, P. , J. Am. Chem. Soc. (1975), 97 (4), 800-807,3. 09 g, 18.1 mmol) in acetic acid (24 mi) and water (36 ml) was added dropwise the solution of the diazonium salt, followed by sodium acetate (24.2 g) in water (42 ml). The reaction mixture was then stirred at room temperature for 30 min. The reaction mixture was poured into ice/water (200 ml) and the mixture was extracted with dichloromethane (4 x 60 ml). The combined extracts were then washed with ammonium hydroxide (48 ml), dried and concentrated in vacuo. To a solution of sodium methoxide (25 wt. percent, 11.5 ml, 50.1 mmol) in methanol (450 ml) was added dropwise a solution of the residue in methanol (100 ml). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and to the residue was added water. This solution was adjusted to pH 1 by addition of hydrochloric acid (4N) and the mixture was extracted with dichloromethane (3 x 100 ml). The combined extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography, eluting with hexane/ethyl acetate [3: 1]. The appropriate fractions were combined and concentrated to give the titled compound (4. 5g). Experimental MH+ 379.8 ; expected 380.0

The synthetic route of 6283-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/90313; (2005); A1;,
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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 64113-85-5 as follows. category: nitriles-buliding-blocks

General procedure: The heterocyclic derivative (0.99 mmol) and 5 mL THF is cooled to -78 oC, n-BuLi solution ( 0.5, mL, 1.2 eq) is added, the mixture is stirred 1 hr, after which 2-cyano-4-methyhlbiphenyl (192 mg, 0.99 mmol, dissolved in 5 mL THF) is added dropwise, The solution is then stirred 1 hr at -78 oC, then allowed to warm to room temperature and stirred for 6 hr. After this, 10 mL of 6M HCl is added and the mixture is stirred overnight. The solution is then basified with 10M NaOH and the products are partitioned between ether and water. The aqueous layer is further extracted (2x with ether) and the combined extracts are washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent is then removed under reduced pressure and the crude mixture is purified by column chromatography (1:1, hexanes: ethyl acetate).

According to the analysis of related databases, 64113-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stentzel, Michael R.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 60; 25; (2019); p. 1675 – 1677;,
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