Month: February 2021

Reference of 4513-77-3, The chemical industry reduces the impact on the environment during synthesis 4513-77-3, name is 2-Oxocyclohexanecarbonitrile, I believe this compound will play a more active role in future production and life.

General procedure: The corresponding 2-hydrazino-benzoic acid or methyl-2-hydrazinobenzoate (1.1 mmol) and the alpha-oxo-cyano compound (1 mmol) were suspended in dry ethanol (5.5 ml) and refluxed for 3 h. After cooling, the product was precipitated, filtered, and dried in vacuo to yield the title products.

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

Reference:
Article; Kovacs, Daniel; Molnar-Toth, Judit; Blasko, Gabor; Fejes, Imre; Nyerges, Miklos; Synthetic Communications; vol. 45; 14; (2015); p. 1675 – 1680;,
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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. 4110-35-4, name is 3,5-Dinitrobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3,5-Dinitrobenzonitrile

Example 19 – Preparation of 3-Amino-5-[(7-chloroquinolin-4-yl)amino] benzonitrile hydrochloride (compound 73); Step A: 3,5-Diaminobenzonitrile; To 3,5-dinitrobenzonitrile (5.0 g, 25.89 mmol) in 20 mL of HCI 1 M, was added SnCI2 (34.4 g, 7 eq). The reaction mixture was stirred at room temperature for 2h and then cooled to O’C. The mixture was made alkaline with a 50% aqueous solution of NaOH and the precipitate was removed by filtration. The filtrate was extracted with ethyl acetate and the combined organic layers were evaporated. The residue and the precipitate were purified by flash chromatography on silica gel (DCM/MeOH//95/5) to yield expected compound as an orange solid (1 .95 g, 57% yield), m/z (ESI) 134.0 [M+H]+.

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; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); UNIVERSITE LILLE 2 DROIT ET SANTE; DELACOURTE, Andre; MELNYK, Patricia; BURLET, Stephane; LEFUR, Nicolas; WO2011/73322; (2011); A1;,
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Related Products of 630-18-2,Some common heterocyclic compound, 630-18-2, name is Pivalonitrile, molecular formula is C5H9N, 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 catalytic activity of 5 mol % [RuCl2(PTA)4] toward nitrile hydration was evaluated in aqueous solution at 100 C. with 1 mmol nitrile in a culture tube under air (Scheme 2). Under the conditions described here, RuCl3 (5 mol %) provided a 54% conversion of benzonitrile to benzamide in 24 hours. Benzonitrile hydration by 2 mol % RuCl3 was previously reported to yield 28% benzamide after 3 h at 130 C. No hydration was observed in the absence of a catalyst, or with PTA, [RuCl2(eta6-toluene)]2, or [RuCl2(PPh3)3] as catalysts. Benzonitrile hydration by [RuCl2(PTA)4] did not occur at 50 C. and provided only 23% conversion after 24 h at 75 C. The hydration of benzonitrile catalyzed by [RuCl2(PTA)4] showed a >99% conversion to benzamide at 100 C. after 7 hours, in contrast to the inactive [RuCl2(PPh3)3], potentially demonstrating a cooperative effect of the nitrogen-containing PTA versus PPh3. For comparison, nitrile hydration catalyzed by 5 mol % [RuCl2(eta6-arene)(PTA)] (eta6-arene=benzene, p-cymene, 1,3,5-trimethylbenzene, and hexamethylbenzene), showed >98% conversions in 4-9 h for aqueous benzonitrile hydration under N2 at 100 C. An in situ generated catalyst formed by the addition of RuCl3 hydrate with 6 equivalence of PTA provided results similar to the preformed complex RuCl2PTA4 (Table 1).The conversion of various nitriles (1a-1n) to the corresponding amides (2a-2n) was explored with results summarized in Table 1. All nitriles were efficiently converted to amides with 67-99% conversion in 7 hours and >99% conversions by 24 hours, with the exception of 2-cyanopyridine (1j, 81% after 24 h). After completion, the reaction was cooled to 0 C. and, in most cases, the product amides crystallized out as white needles and were easily isolated in 67-81% yield by decantation. Identity of the isolated amides (2a-2n) was confirmed by GC-MS and NMR spectroscopy. Substituted benzonitriles bearing electron-withdrawing groups (Table 1 above, entries 1g-1i) exhibited slightly more efficient conversions to amides than those with electron-donating groups (entries 1b-1f). Presumably, the presence of the electron-withdrawing group makes the nitrile carbon more susceptible to nucleophilic attack by an activated water molecule. As previously reported for ortho-substituted benzonitriles, o-tolunitrile exhibited lower conversion relative to m- and p-tolunitriles (Table 1, entries 1b-1d), which is attributed to steric hindrance of the o-tolunitriles. Hydration of 4-cyanobenzaldehyde led to 4-formylbenzamide in a 99% conversion in 7 h with an intact formyl moiety (entry 1i). The coordinating ability of the pyridyl functionality reduced catalytic activity as hydration of 2-cyanopyridine to picolinamide resulted in only 81% conversion after 24 h (entry 1j).[RuCl2(PTA)4] was also effective as a hydration catalyst for the less reactive aliphatic nitriles (Table 1, entries 1k-1m). 4-Methylbenzyl cyanide was transformed with 99% conversion in 7 hours (entry 1k) into the amide. Hydration of the sterically bulky pivalonitrile (1m) to pivalamide proceeded with a 99% conversion in 24 h although a modest conversion of 67% was observed after 7 h (entry 1m). The resistance of tertiary nitriles toward hydrolysis has been noted. The industrially important acrylonitrile was almost quantitatively converted into acrylamide in 7 hours without observation of polymerization or hydrolysis byproducts (Table 1, entry 1n). For all the nitrile hydrations studied, the corresponding amides were the only product observed (no carboxylic acids were detected by GC-MS). Thus, the catalytic conditions described here are compatible with ether (entry 1e), hydroxyl (entry 10, nitro (entry 1g), bromo (entry 1h), formyl (entry 1i), pyridyl (entry 1j), benzyl (entry 1k), alkyl (entries 1l-1m), and olefinic (entry 1n) functional groups, which establishes a wide synthetic scope.

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

Reference:
Patent; Board of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada; Frost, Brian J.; Lee, Wei-Chih; US2013/96344; (2013); A1;,
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These common heterocyclic compound, 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, 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. COA of Formula: C9H6FNO

400 g of phosphorus pentoxide 4000 g of mesyl acid Followed by stirring at 50 C for 3 hours. After cooling to 20-25 C, 118.5 g of cyclooctanone of Formula 2 and 153.3 g of 3-(4-fluorophenyl)-3-oxopropanenitrile of Formula 3 were added and stirred at 50 C for 12 hours. The reaction mixture was extracted with water and dichloromethane, and the organic layer was washed with brine, followed by adding anhydrous sodium sulfate and activated charcoal, followed by filtration and distillation. Recrystallization from ethyl acetate and hexane gave 95% yield 4-(4-fluorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2 (1H)-one

The synthetic route of 3-(4-Fluorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kukjeon pharmaceutical.Co.,Ltd.; Hong, Jong Ho; Jo, Ir Hwan; Kim, Sung Han; Moon, Jong Taek; Kim, Eun Jung; Kim, Jae Young; (5 pag.)KR2016/49217; (2016); A;,
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Related Products of 1813-33-8, The chemical industry reduces the impact on the environment during synthesis 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

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).

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-Chloro-4-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

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;,
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15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, 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. Recommanded Product: 15760-35-7

3 -oxocyclobutanecarbonitrile [1266] A mixture of 3-methylenecyclobutanecarbonitrile (9.39 g, 101 mmol), dichloromethane (200 mL), water (300 mL), acetonitrile (200 mL), and ruthenium(III) chloride hydrate (0.500 g, 2.218 mmol) was cooled to <5 C, followed by portionwise addition of sodium periodate (88 g, 413 mmol) at <20 C, and stirred for 10 minutes. The mixture was diluted with dichloromethane and partitioned. The organic phase was filtered through a silica pad, dried ( a2S04), filtered, concentrated, and passed through a silica plug again, eluting with 200 mL dichloromethane to provide Example 125A (8.21 g, 86 mmol, 86 % yield) as a white solid. XH NMR (300 MHz, CDC13) ? 3.60 - 3.22 (m, 5H). The synthetic route of 15760-35-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
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Electric Literature of 2469-99-0, 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. 2469-99-0, name is 3-Oxobutanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of (4-fluorophenyl)hydrazine (HCl salt, 802 mg, 5.8 mmol) and 3-oxo-butyronitrile (500 mg, 5.8 mmol) in EtOHIAcOH (10 mL/0.2 mL) was stirred at refluxing overnight. The reaction solution was concentrated in vacuum to give crode 2-(4-fluorophenyl)-5-methyl-2H-pyrazol-3-ylamine (1.1 g, yield:quantitative) as a yellow solid which was used for the next step without any purification. ?H NMR (400 MHz,DMSO-d6): = 7.6-7.64 (m, 2H), 7.45 (t, J= 8.8 Hz, 1H), 5.66 (s, 1H), 2.24 (s, 3H).

The synthetic route of 3-Oxobutanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; HASSIG, Christian, A.; JACKSON, Michael, R.; ARDECKY, Robert, John; PASS, Ian; (436 pag.)WO2016/123392; (2016); A2;,
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Related Products of 215800-25-2, 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. 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-bromo-3-methylphenylacetonitrile (1 g, 4.76 mmol) and methanol (10 mL) were added to a 25 mL singlemouth bottle, and thionyl chloride (5 mL) was added under ice bath. After reacted under ice bath for 20 minutes, the obtained mixture reacted at room temperature overnight. After completion of the reaction, the mixture was concentrated in vacuo to remove the solvent to give the product (colorless oil, 1 g), with a yield of 64.1%. 1H NMR (400 MHz, CDCl3) delta 7.47 (d, J = 8.1 Hz, 1H), 7.15 (s, 1H), 6.96 (dd, J= 8.2, 1.6 Hz, 1H), 3.69 (s, 3H), 3.55 (s, 2H), 2.38 (s, 3H).

The synthetic route of 2-(4-Bromo-3-methylphenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; YU, Fazhi; TANG, Ting; EP3476829; (2019); A1;,
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Reference of 3939-09-1, A common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Example II-2 45 g (0.9 mol) of hydrazine hydrate are added dropwise with stirring to 90 g (0.65 mol) of 2,4-difluorobenzonitrile (cf., for example, EP-A 122,693) in 300 ml of methanol, the mixture is heated at reflux temperature for 3 hours and then concentrated in vacuo, and the residue is stirred with 300 ml of water, filtered off with suction and dried. 73 g (74% of theory) of 4-cyano-3-fluorophenylhydrazine of melting point 136 C. are obtained.

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; Bayer Aktiengesellschaft; US6906006; (2005); B1;,
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Related Products of 4426-11-3,Some common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, molecular formula is C5H7N, 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.

A mixture of cyclobutanecarbonitrile (0.70 g, 8.6 mmol) and 2-chloro-6-fluorobenzoic acid (0.5 g, 2.9 mmol) in THF (9.6 mL) at 0 C.Was added KHMDS (0.5 M in toluene, 12.6 mL, 6.3 mmol). The resulting mixture was heated at 70 C. for 3 h, then cooled and concentrated in vacuo. The residue was taken up in 20 mL H 2 O and extracted three times with Et 2 O. The aqueous layer was acidified with 2 N HCl and extracted with CHCl 3 / i-PrOH (3: 1). The combined organic portion was dried over Na 2 SO 4 and concentrated. This crude residue was used directly.

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

Reference:
Patent; Mrck Sharp and Dohme Corp; Blair T, Lapointe; Peter H, Fuller; Hakan, Gunaydin; Kun, Liu; Daneille F, Molinari; Qinglin, Pu; Mark E, Scott; B Wesely, Trotter; Hongjun, Zhang; (117 pag.)JP2018/531957; (2018); A;,
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