Author: Jessica.F

Reference of 25978-68-1, These common heterocyclic compound, 25978-68-1, name is Methyl 4-cyano-3-methylbenzoate, 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.

Lithium borohydride (33 mg, 1.54 mmol) was added into a solution of methyl 4-cyano-3- methylbenzoate (245 mg, 1.40 mmol) in THF (3 ml.) and the resulting mixture was stirred at RT for 4 hours. The reaction mixture was diluted with water (10 ml.) and extracted with EtOAc (4×20 ml_). The combined organic fractions were dried (MgSO4) and concentrated under vacuum. The residue was purified by flash chromatography (silica, petrol ether/EtOAc) to give the title compound as a colorless gum (195 mg, 95%). 1H NMR (CDCI3, 400 MHz) delta 7.58 (1 H, d, J=7.9 Hz), 7.33 (1 H, s), 7.26 (1 H, m), 4.74 (2H, s), 2.55 (3H, s), 1.95 (1 H, s). LC/MS (Method A): 144 (M+H)+. HPLC (Method F) Rt 3.95 min (Purity: 95.3%).

The synthetic route of 25978-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
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Electric Literature of 134450-56-9, 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. 134450-56-9, name is 4,5-Difluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of compound of formula XVIII is illustrated in Scheme 3 below. (0146) Reaction of 0.5 molar equivalents of carbazole with 4,5-difluorophthalonitrile affords compound 8 which is then reacted with 4 to provide intermediate 9. Hydrolysis of the nitrile functions provides dicarboxylic acid 10 on acidification. Methylation with iodomethane and anion metathesis with saturated NH4PF6 solution provides the product XVIII.

The chemical industry reduces the impact on the environment during synthesis 4,5-Difluorophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS; Zysman-Colman, Eli; Wong, Michael Yin; (41 pag.)US2017/352818; (2017); A1;,
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Synthetic Route of 20249-16-5,Some common heterocyclic compound, 20249-16-5, name is 3-Oxocyclobutanecarbonitrile, molecular formula is C5H5NO, 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 lithium (Z)-l-(5-bromo-2-methoxypyridin-3-yl)-2- (dimethoxvphosphoryl)ethenolate (2.0 g, 5.8 mmol) and 3-oxocyclobutanecarbonitrile (1.1 g, 12 mmol) in p-dioxane (6 ml) was heated at 1200C by Microwave in Ih. The mixture was cooled, taken up in H2O, extracted with EtOAc (3x), dried over MgSO4, concentrated to provide the title compound. MS (m+1): 307.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Oxocyclobutanecarbonitrile, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2008/147544; (2008); A1;,
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Related Products of 60899-34-5,Some common heterocyclic compound, 60899-34-5, name is 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, molecular formula is C10H7NO, 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 the stirred mixture of 50.0 gm of 4-cyano-l-indanone (Formula 3) (0.318 moles) and 500 ml of heptane, 60 gm of (S)-(-)-l-(4-methoxyphenyl)ethylamine (Formulal3) (0.398 moles, 1.25eq.) was added at ambient temperature. The resulting mixture was heated to 100-105C and water was removed azeotropically. After 15.0 hrs, the reaction mass was cooled to 25-30C and stirred for 1.0 hr. The product was filtered, washed with heptane and dried to obtain a light brown solid of compound of Formulal4(84.0 g, 90.93% yield) with HPLC purity 94.35% & SOR -72 (c=0.1 in CHC13at 20C).MR: 130.4-132.1C; IR (KBr, cm”1): 2226, 1661, 1611, 1513, 1245, 1030; 1H- NMR(CDC13): delta 8.11-8.09 (d, 1H, J=7.74Hz), 7.66-7.64 (d, 1H, J=7.47Hz),7.41-7.89 (m, 3H), 6.89-6.87 (d, 2H, J=8.50Hz), 4.66-4.61 (q, 1H, J=6.46, 12.96 Hz), 3.79 (s, 3H), 3.26-3.21 (m, 2H), 2.90-2.88 (m, 1H), 2.78-2.73 (m, 1H), 1.56-1.55 (d, 3H, J=6.49Hz);13C-NMR(CDCl3): 169.99, 158.48, 152.56, 141.66, 137.59, 134.28, 127.72, 127.66 (2C),127.15,117.12, 113.87(2C), 109.93, 61.56, 55.32, 27.85, 27.67, 24.77;MS (m/z): 291.1 [M+l]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Oxo-2,3-dihydro-1H-indene-4-carbonitrile, its application will become more common.

Reference:
Patent; SUVEN LIFE SCIENCES LIMITED; CHINNAPILLAI, Rajendiran; PERIYANDI, Nagarajan; JASTI, Venkateswaralu; (33 pag.)WO2019/58290; (2019); 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. 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3-(4-Bromophenyl)-3-oxopropanenitrile

General procedure: A dry 50 mL round flask equipped with a magnetic stirring bar was charged with a solution of 3-oxo-3-phenylpropanenitrile (0.87 g, 6.0 mmol), benzaldehyde (0.61 mL, 6.0 mmol), piperidine (0.12 mL, 0.2 equiv), and acetic acid (0.069 mL, 0.2 equiv) in toluene (20 mL). The mixture was heated at 60 C for 12 h. After cooling to room temperature, the mixture was washed with water (10 mL) and the aqueous phase was extracted with ethyl acetate (3×10 mL). The crude mixture was subjected to column chromatography (PE/EA 98:2) to yield 0.68 g (2.9 mmol, 48%) of the desired product as a white solid.

According to the analysis of related databases, 4592-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Wen; Zhou, Jing; Zheng, Changwu; Chen, Xingkuan; Xiao, Hua; Yang, Yingquan; Guo, Yinlong; Zhao, Gang; Tetrahedron; vol. 67; 10; (2011); p. 1768 – 1773;,
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Some common heterocyclic compound, 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, molecular formula is C12H6N2O, 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: C12H6N2O

As shown in the above reaction formula,The compound of the formula (2-9-1) obtained in the above Preparation Example 2 (157.4 mg,0.1mmol),a compound of the formula (a-2-1) (78 mg, 0.4 mmol; purchased from TCI),Pyridine (0.8 mL, 0.96 mmol)Add chloroform (30 mL) to the reaction vessel and pass argon for 25 min.It was then refluxed at 65 C for 15 h.After cooling to room temperature (about 25 C), the reaction product was poured into 200 mL of methanol and filtered, and the resulting precipitate was chromatographed on silica gel (using 200-300 mesh).Separation of silica gel with eluent in a volume ratio of 1:2 petroleum ether/dichloromethane to give a blue solid(173.6 mg, yield 90.1%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1080-74-6, its application will become more common.

Reference:
Patent; Peking University; Zhan Xiaowei; Wang Jiayu; (33 pag.)CN108794504; (2018); A;,
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Reference of 766-84-7, 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 766-84-7 as follows.

General procedure: An equimolar mixture of 2-aminoethanol (1.0 mmol) and sulfur(1.0 mmol) was heated under solvent-free condition at 50C. Nitrile (1.0 mmol) was then added to reaction mixture and refluxed at 80C. The progress of the reaction was monitored through TLC (n-hexane: EtOAc, 8:2). After completion of the reaction, excess of water was added, and the product was filtered (for solid). Further chromatographic purification afforded pure product. All the compounds were characterizedby infrared (IR) and 1H NMR and 13C NMR spectroscopic data, as well as by comparison with data of reported compounds.

According to the analysis of related databases, 766-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bansal, Shivani; Gupta, Poonam; Halve; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 7; (2016); p. 971 – 974;,
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Related Products of 1558-82-3, A common heterocyclic compound, 1558-82-3, name is Ethyl N-cyanoacetimidate, molecular formula is C5H8N2O, 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 7 Preparation of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-[N-methyl-(N-cyano-acetimidoyl)amino]-2H-benzo[b]pyran-3-ol To 2.80 g of ethyl N-cyanoacetimidate, 4.65 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-methylamino-2H-benzo[b]pyran-3-ol was added, and the mixture was reacted under stirring at a temperature of from 100 to 120 C. for 2 hours. The reaction mixture was cooled, then dissolved in 100 ml of ethyl acetate, washed twice with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residual solid was recrystallized from ethanol to obtain 2.34 g of the above identified compound in the form of crystals. Melting point: 250-251 C.

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; Kaken Pharmaceutical Co., Ltd.; US5095016; (1992); A;,
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Electric Literature of 501-00-8, 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(3- fluorophenyl)acetonitrile (100 g, 0.74 mol) in Dry DMF (1000 ml) was added 1,5- dibromopentane (170 g, 0.74 mol), NaH (65 g, 2.2 eq) was added dropwise at ice bath. After addition, the resulting mixture was vigorously stirred overnight at 50C. The suspension was10 quenched by ice water carefully, extracted with ethyl acetate (3*500 ml). The combined organic solution was concentrate to afford the crude which was purified on flash column to give 1-(3-fluorophenyl)cyclohexanecarbonitrile as pale solid (100 g, 67%).

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

Reference:
Patent; UNIVERSITY OF MODENA AND REGGIO EMILIA; COSENZA, Maria; POZZI, Samantha; (78 pag.)WO2016/87950; (2016); A1;,
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Related Products of 38487-86-4, A common heterocyclic compound, 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

[00393] Intermediate 34A. 2-Azido-4-chlorobenzonitrile: To a solution of 2-amino-4- chlorobenzonitrile (2.0 g, 13.11 mmol) in TFA (12 mL) was added water (2.4 mL). After cooling to 0 C, sodium nitrite (0.904 g, 13.11 mmol) was added over a period of 0.5 h. After this addition, sodium azide (2.164 g, 33.3 mmol) in water (5 mL) was gradually added dropwise. The reaction was stirred at 0 C for 10 min, and then allowed to warm to room temperature. After 2 h, quenched the reaction with water (100 mL) and insoluble solid was filtered and dried under suction and nitrogen. Aliquot LCMS analysis indicated starting material disappeared and a new peak formed which was not ionizing.

The synthetic route of 38487-86-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
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