Tag: M.W=100-200

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. 3100-67-2, name is 1-Amino-2-naphthonitrile, A new synthetic method of this compound is introduced below., Safety of 1-Amino-2-naphthonitrile

A solution of [Intermediate 7-a] (18.5 g, 0.11 mol) in dimethyl formamide (200 mL) was stirred at 0 C. Drops of a solution of N-bromosuccinimide (20.1 g, 0.11 mol) in dimethyl formamide (100 mL) were slowly added over 1 hr. The reaction mixture was warmed to room temperature and stirred for 12 hrs. Following filtration with an excess of distilled water, the filtrate was washed with methanol and recrystallized in toluene and methanol to afford [Intermediate 7-b] (18.7 g): yield 69%.

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; SFC CO., LTD.; LEE, Chang-Hee; SEO, Hyun-JONG; YOON, Seo-Yeon; SHIM, So Young; KIM, Si-In; (214 pag.)US2018/233669; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 53005-44-0, name is 2-Methoxy-6-methylbenzonitrile, molecular formula is C9H9NO, 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. Recommanded Product: 53005-44-0

To intermediate 145 (5.0 g, 34.03 mmol) in THF (50 ml), benzylmagnesium chloride (34 ml, 2M in THF, 68.02 mmol) was added at 0C over 30 min. and heated to reflux for 15 h. The reaction mixture was cooled to room temperature, 2N HC1 (200 ml) was added and again refluxed for 4h. The reaction mixture was cooled and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford to afford the title compound as brown liquid (3.7 g , 45%). -NMR (delta ppm, CDCI3, 400 MHz): 7.30-7. 18 (m, 6H), 6.76 (m, 2H), 4.07 (s, 2H), 3.83 (s, 3H), 2.02 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53005-44-0, its application will become more common.

Reference:
Patent; RHIZEN PHARMACEUTICALS SA; NAGARATHNAM, Dhanapalan; VAKKALANKA, Swaroop Kumar, V.S.; MUTHUPPALANIAPPAN, Meyyappan; VISWANADHA, Srikant; BABU, Govindarajulu; BHAVAR, Prashant, Kashinath; WO2012/151525; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 31603-77-7,Some common heterocyclic compound, 31603-77-7, name is 4-Biphenylacetonitrile, molecular formula is C14H11N, 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: To a solution of arylacetonitrile (10 mmol) (2-(4-bromophenyl)acetonitrile) in dried THF (10 mL), LDA (2.0 M in THF, 20 mL, 40 mmol) was added under N2 atmosphere in an ice-bath. The solution was stirred at 45 C for 1 h. After cooling the reaction mixture again to 0 C, iodomethane (60 mmol) was added drop wise. The reaction was stirred overnight at room temperature, quenched by 4 N HCl at 0 C and then diluted with Et2O. The phases were separated and the aqueous phase was extracted with Et2O (3 times). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4. After filtration and concentration, the crude acid was purified by flash column chromatography to give the desired product as a white or pale yellow solid. The next step of the hydrolysis was done by the reported procedures.

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

Reference:
Article; Hajipour, Abdol R.; Khorsandi, Zahra; Tetrahedron Letters; vol. 61; 3; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 508203-48-3,Some common heterocyclic compound, 508203-48-3, name is 2,3-Difluoro-4-methylbenzonitrile, molecular formula is C8H5F2N, 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 a suspension of 2,3-difluoro-4-methylbenzonitrile (5.0 g, 32.6 mmol) in ethanol (1 1 1 ml_) at 25C was added hydroxylamine hydrochloride (4.5 g, 65.3 mmol). The reaction mixture was heated at 80C for 2 hours. After cooling to room temperature the volatiles were removed under reduced pressure thus affording a white solid that was used in the next step without purification. NMR (400 MHz, CDCIs) d ppm: 7.30 (m, 1 H), 6.95 (m, 1 H), 5.05 (brs, 2H), 2.30 (s, 3H).

The synthetic route of 508203-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; PITTERNA, Thomas; STIERLI, Daniel; RAJAN, Ramya; (85 pag.)WO2019/207058; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 127510-95-6, name is Methyl 2-cyano-5-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 127510-95-6, COA of Formula: C10H9NO3

5′-Methoxy-spiro[cyclopropane-11 ‘-isoindol]-3′(2’H)-one5 To a flask containing 2-Cyano-5-methoxy-benzoic acid methyl ester (10.22 g, 53.4 mmol), titanium (IV) isopropoxide (17 g, 61 mmol) and diethyl ether (200 mL) was added a solution of 3 M ethyl magnesium bromide in diethyl ether (36 mL, 107 mmol) at 0 “C. The mixture was allowed to warm to room temperature over 3 hours upon which an aqueous solution of 1 N HCI (200 mL) was slowly added. The black mixture was filtered through 400 g Q of celite and the filtrate was concentrated and absorbed onto silica in order to perform chromatography (0-100 % ethyl acetate: hexanes) to yield 5′-Methoxy-spiro[cyclopropane-11’- isoindol]-3′(2’H)-one (3.9 g, 38 %) MS: ES M+1 190.1 (189.2).

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 2-cyano-5-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

185147-06-2, name is 3-Fluoro-2-methylbenzonitrile, 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: 185147-06-2

A solution of the compound 2A (50 g, 0.37 mol) in CCI4 (500 mL) was added the NBS (72.5 g, 0.408 mol) and the AIBN (1 .2 g, 0.037 mol), the reaction solution was refluxed for overnight, TLC indicated the reaction was completed, the reaction solution was filtered and concentrated in vacuum to give the crude product which was purified by flash silica chromatography eluting with petroleum ether/EtOAc (500:1 ) to give the desired compound 2B (30 g, yield: 40%) as a white solid.

The synthetic route of 185147-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; MARIGO, Mauro; KILBURN, John Paul; NIELSEN, Jacob; PUeSCHL, Ask; LANGGARD, Morten; JESSING, Mikkel; KEHLER, Jan; WO2013/45607; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 13989-82-7, name is 4-(Dimethylamino)butanenitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-(Dimethylamino)butanenitrile

To a suspension of lithium aluminum hydride (LAH) (4.74 g, 120.90 mmol) in dry ether (100 ml) was added dropwise a solution of N-(3-cyanopropyl)-N,N-dimethylamine 321 (4.10 g, 36.61 mmol) in dry ether (50 ml) at 0 C. After complete addition, the reaction mixture was stirred for two hours while allowing the temperature to raise from 0 C. to room temperature. The reaction mixture was quenched with 2N NaOH at 0 C. and the resulting white suspension was filtered through Celite and washed with ether. The ether filtrate was dried over K2 CO3, filtered and concentrated in vacuo, yielding N,N-dimethyl-1,4-diaminobutane 322 as a colorless oil (2.5 g, 60% yield). 1 H NMR (400 MHz, CDCl3) delta: 1.43 (4H, m, –CH2 –CH2 –CH2 –CH2 –), 1.93 (2H, br s, –NH2), 2.16 (6H, s, –N(CH3)2), 2.21 (2H, t, –CH2 CH2 N), 2.66 (2H, t, –CH2 CH2 NH2).

According to the analysis of related databases, 13989-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Magainin Pharmaceuticals, Inc.; US5637691; (1997); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 55984-93-5, 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. 55984-93-5, name is 2-Methylterephthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methylterephthalonitrile (1.42 g, 1.0 mmol) and t-butoxybis(dimethylamine)methane (3.5 g, 2.0 mmol) were heated with 15 mL of DML at 75 ¡ãC for 12 h under N2. The DMF was removed and hexane was added. The precipitate formed was filtered and dried to give 1.85 g of the desired product. MS: 504.4, (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-Methylterephthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/123050; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 31603-77-7 as follows. category: nitriles-buliding-blocks

EXAMPLE 53 (6-Biphenyl-4-yl-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of 2-ethoxyethanol was added 4-biphenylaceto-nitrile (263 mg, 1.36 mmol). After stirring for 5 minutes at room temperature, 4-ethylamino-2-phenylamino-pyrimidine-5-carboxaldehyde (300 mg, 1.24 mmol) was added and the reaction heated at 110 C. for 1 hour, resulting in a dark brown solution. Upon cooling, the solution was poured into water which caused precipitation. The resulting precipitate was removed by filtration and washed with water. The crude product was purified by flash chromatography, eluding with 5% methanol/methylene chloride, followed by 10% methanol/methylene chloride. Concentration of product fractions yielded 427 mg (83%) of (6-biphenyl-4-yl-8-ethyl-7-imino-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yl)-phenylamine; mp 245-249 C. Mass spectrum (CI) 418 (M+). Analysis calculated for C27 H23 N5: C, 77.67; H, 5.55; N, 16.78. Found: C, 76.16; H, 5.54; N, 16.36.

According to the analysis of related databases, 31603-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Warner-Lambert Company; US5945422; (1999); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 1528-41-2, 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. 1528-41-2, name is Ethyl 2-(4-cyanophenyl)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 50 ethyl 2-(4-cyanophenyl)-3-(dimethylamino)acrylate [0235] Combined ethyl 2-(4-cyanophenyl)acetate (25 g, 0.132 mol) with DMF-DEA (60 mL) and heated to 70C for 3 hours. The reaction mixture was cooled to room temperature and concentrated and then purified by flash chromatography to give the title compound (20 g, 62%) as a solid. XH NMR (400 MHz, DMSO-i) delta ppm 7.71 (d, J=8.4Hz, 2H), 7.59 (s, 1H), 7.29 (d, J=8.4Hz, 2H), 4.03 (q, J=6.8Hz, 2H), 2.67 (s, 6H), 1.13 (t, J=6.8Hz, 3H).

The synthetic route of Ethyl 2-(4-cyanophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts