Author: Jessica.F

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. 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 2-Amino-4-methoxybenzonitrile

To a stirred solution of 2-amino-4-methoxy benzonitrile (19.4 g, 131 mmol) in acetonitrile (582 mL) was added NBS (18.66 g, 104 mmol) and the mixture was stirred for 1 h at 0 C. The reaction was quenched by addition of ice. The volatiles were concentrated under reduced pressure and the residue was extracted with ethylacetate (2 x 200 mL). The combined organic layers were washed with brine solution (200 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 2-amino-5-bromo-4-methoxy benzonitrile (26 g, 114 mmol, 87% yield) as a brown solid. LCMS (ESI) m/e 227.6 (bromo pattern) [(M+H), calcd for C8H8BrN2O, 227.06]; LC/MS retention time (method C): ti = 1.46 mm.

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; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); A1;,
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Related Products of 31603-77-7, 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. 31603-77-7, name is 4-Biphenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-([1,1′-biphenyl]-4-yl) acetonitrile I (e.g. Sigma-Aldrich, catalogue no.133612, CAS no. 31603-77-7) (100 g, 517.46 mmol) in ethylene glycol (1000 mL), a solution of potassium hydroxide (590 g, 10515 mmol) in water (1000 mL) was added and the resulting mixture was heated to 120 C and stirred for 16h. The reaction mixture was cooled to 0 C and acidified with concentrated HCI with stirring. The solid separated out wascollected by filtration, washed with water and dried. The solid was dissolved in ethyl acetate and the ethyl acetate layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure to get white solid. The solid was taken in petroleum ether, stirred for -30 mm, filtered and dried to get 2-([i,i-biphenyl]-4-yl)acetic acid 2 as white solid. (107.2 g, 97.6%).1H-NMR (400 MHz, DMSO-d6): 3 12.41 (br. s, 1 H), 7.59-7.66 (m, 4 H), 7.44-7.47 (m, 2 H);7.34-7.37 (m, 3 H), 3.61 (5, 2 H) ppm; MS (MM-ES, APCI): negative mode 257.0 [M +HCO2f.

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

Reference:
Patent; NOVARTIS AG; KLEINBECK-RINIKER, Florian Karl; MARTIN, Benjamin; PENN, Gerhard; VENTURONI, Francesco; SCHLAMA, Thierry; RUCH, Thomas; ALLMENDINGER, Thomas; WIETFELD, Bernhard; FILIPPONI, Paolo; (104 pag.)WO2017/98430; (2017); A1;,
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Some common heterocyclic compound, 4107-65-7, name is 2,4-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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. category: nitriles-buliding-blocks

Step a 2,4-dimethoxybenzonitrile (2 g) was mixed with pyridinium chloride (5.67 g) and the reaction mixture was fused at 210 C. for 2 hours. After being left to stand at room temperature overnight, the mixture was diluted with water and extracted into diethyl ether. The ether extracts were washed with water, dried over magnesium sulphate and concentrated to give a pink solid which was washed with petrol and air dried to give 2,4-dihydroxybenzonitrile (1.17 g) (m pt 176-178 C.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4107-65-7, its application will become more common.

Reference:
Patent; Imperial Chemical Industries plc; US5120869; (1992); A;,
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Application of 5332-06-9, 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 5332-06-9 as follows.

General procedure: To a stirred solution of N-norhydromorphone (S10 in the SupplementaryMaterials, 0.406 g, 1.5 mmol) in DMF (10 mL) were added NaHCO3 (0.504 g, 6 mmol) and 1-(2-bromoethyl)-4-chlorobenzene (0.480 mL, 3.3 mmol). The mixture was heated at 90 C overnight,cooled to room temperature, filtered through Celite, and concentrated in vacuo. Water (10 mL) wasadded and the mixture extracted with CHCl3 (3 × 20 mL). The combined organics were washed withH2O (5 × 20 mL), dried over Na2SO4, filtered through Celite, and concentrated in vacuo to afford 2ifree base as a crude colorless oil. Purification of this oil by SiO2 column chromatography with 10%NH4OH in MeOH/CHCl3 (gradient, 0 ? 4% of 10% NH4OH) afforded 2i (0.420 g, 70%) as a colorlessoil.

According to the analysis of related databases, 5332-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Adler, Martin W.; Bergman, Jack; Chadderdon, Aaron M.; Crowley, Rachel Saylor; Geller, Ellen B.; Hanna, Ramsey D.; Hassan, Sergio A.; Herdman, Christine A.; Inan, Saadet; Irvin, Thomas C.; Jacobson, Arthur E.; Kaska, Sophia; Katz, Jonathan L.; Kopajtic, Theresa A.; Lee, Yong-Sok; Paronis, Carol A.; Prisinzano, Thomas E.; Rice, Kenner C.; Traynor, John R.; Wang, Meining; Withey, Sarah L.; Molecules; vol. 25; 11; (2020);,
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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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Amino-3-chlorobenzonitrile

Step 8 – Synthesis of Compound 6; To a stirred solution of sodium hydride (0.08 g, 0.2.07 mmol) in tetrahydrofuran (6 ml) in a sealed tube was added a solution of 4-amino-3-chloro benzonitrile (0.06 g, 0.42 itimo.) in tetrahydrofuran (9 mL) and the resulting reaction was allowed to stir for about 45 minutes. The reaction mixture was then cooled to 00C and a solution of compound IJ (0.15 g. 0.41 mmol) in tetrahydrofuran (9 mL) was added and the resulting reaction was heated to reflux and allowed to stir at this temperature for about 15 hours. The reaction was cooled to room temperature, quenched with water and extracted 2 times with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated in vacuo. The resulting residue was purified using preparative thin layer chromatography (hexane/acetone (80/20)) to provide compound 6 (0.12 g, 60.13%). 6

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; SCHERING CORPORATION; NEELAMKAVIL, Santhosh, Francis; BOYLE, Craig D.; NEUSTADT, Bernard, R.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; WO2010/9208; (2010); A1;,
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Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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. category: nitriles-buliding-blocks

General procedure: To a solution of DAMN (0.54 g, 0.5 mmol) in acetonitrile (5 mL), the appropriate aromatic aldehyde (0.5 mmol) and CAN (5 molpercent) were added. The reaction mixture was stirred at room temperature for 1?3 min. Then, 5 mL acetonitrile and 40 molpercent of CAN were added again and the reaction mixture stirred at 50 °C for the desired time (Table 3). After completion of the reaction (reaction progress was monitored by TLC, ethyl acetate/n-hexane, 2:1), acetonitrile solvent was removed from the reaction mixture, and, by increasing the minimum ethanol and water, a precipitate was formed which was filtered and washed with cold water and ethanol. The product obtained in this way was pure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1187-42-4, its application will become more common.

Reference:
Article; Kalhor, Mehdi; Seyedzade, Zahra; Research on Chemical Intermediates; vol. 43; 5; (2017); p. 3349 – 3360;,
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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. 455-18-5, name is 4-(Trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-(Trifluoromethyl)benzonitrile

1, 4-addition of 50% hydroxylamine aqueous solution (11.6g) in (trifluoromethyl) benzonitrile (10g) solution of ethanol (100), and stirred overnight at 80 C. After the reaction, the solvent was removed by distillation, and water was added. After collecting the insoluble matter was filtered dried to give the N- hydroxy-4- (trifluoromethyl) benzamidine (12.6g). MS (ESI) m / z: 205 (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; Mitsubishi Tanabe Pharma Corporation; Watanabe, Masayuki; Furukawa, Hiroyuki; Hamada, Maiko; Fuji, Naoto; Ushio, Hiroyuki; Takashima, Toru; (81 pag.)KR2015/2661; (2015); A;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-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 36282-26-5, Formula: C7H3BrFN

Sodium hydride (60% suspension in mineral oil, 0.031 g, 0.77 mmol) is added to a solution of 2-bromo-4- fluorobenzonit?le (0.128 g, 0.64 mmol) and 3,4,5- t?methoxyphaneyl acetic acid methyl ester (0.1854 g, 0.77 mmol) in DMF (2 mL) . The reaction mixture is stirred at 60 0C for 3 h. After addition of water (3 mL) , the aqueous phase is extracted with EtOAc (3 x) . The combined organic layers are washed with brine, dried over MgSO4, and evaporated to dryness. The residue is purified by column chromatography (SiO2, 20%-50% EtOAc/hexanes) to yield 0.1363 g (51%) of (3-Bromo-4-cyano- phenyl) – (3, 4 , 5-trimethoxy-phenyl) -acetic acid methyl ester. LC/MS Calculated for Ci9Hi8BrNO5: m/z = 420.26. Found: m/z = 421.8 [M+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, 2-Bromo-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SERENEX, INC.; WO2008/24963; (2008); A1;,
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Electric Literature of 53312-79-1, These common heterocyclic compound, 53312-79-1, name is 3-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.

(1) 4-Chloro-3-(1-nitro-2-naphthylamino)benzonitrile A suspension of 1-nitro-2-naphthyltriflate (1.50 g, 4.67 mmol), 3-amino-4-chlorobenzonitrile (1.05 g, 6.87 mmol), potassium carbonate (645 mg, 4.67 mmol), tetrakis(triphenylphosphine)palladium(0) (162 mg, 0.14 mmol) and triphenylphosphine (65 mg, 0.47 mmol) in toluene (45 mL) was stirred at 110C for 16 hours. The reaction mixture was cooled to room temperature, and filtered. The filtrate was diluted with chloroform, washed with 0.2M hydrochloric acid, a saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 1/1), to give the titled compound (900 mg, yield 60%). 1H-NMR(CDCl3, 400MHz) delta: 7.31(1H, dd, J=2, 8Hz), 7.44(1H, d, J=9Hz), 7.52(1H, t, J=8Hz), 7.58(1H d, J=8Hz), 7.62(1H, d, J=1Hz), 7.68(1H, m), 7.84(1H, d, J=8Hz), 7.96(1H, d, J=9Hz), 8.25(1H, d, J=9Hz), 8.67(1H, br s).

Statistics shows that 3-Amino-4-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 53312-79-1.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; EP2397480; (2011); 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. 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9NO

Step 2: To 5 ml. of dry ethanol was added 0.73 g (31.84 mmol) of sodium metal (after removal of mineral oil with hexane) and the mixture was stirred at 45 C for 1 hour until the solution turned clear. A mixture of 3 g (20.38 mmol) of 3-(methoxyphenyl)acetonitrile and 3.9 g (28.66 mmol) of methyl isonicotinate in 26 ml. of dry ethanol was then added and the resulting brown solution was heated at reflux for 3 hours. After cooling, the residue was evaporated and purified by silica gel chromatography eluting with 9:1 to 4:1 methylene chloride/methanol to provide 1.75 g (34% yield) of 2-(3-methoxyphenyl)-3-oxo-3-pyridin-4-yl-propionitrile.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 19924-43-7.

Reference:
Patent; WYETH; WO2009/108827; (2009); A1;,
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