Category: nitriles-buliding-blocks

57381-44-9, name is 5-Bromo-2-chlorobenzonitrile, 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. HPLC of Formula: C7H3BrClN

3.1.1 2-chloro-5-piperazin-1-yl-benzonitrile (V-1) 0.200 g tert-butyl piperazine-1-carbamidate, 0.235 g 5-bromo-2-chlorbenzonitrile, 0.013 g tris(dibenzylideneacetone)dipalladium(0), 0.018 g rac-BINAP and 0.145 g sodium-tert-butoxide are suspended in 5 ml anhydrous, degassed toluene and heated under argon at 80 C until no further reaction takes place. The reaction mixture is filtered through Celite and mixed with a saturated sodium chloride solution. The product is extracted with ethyl acetate, dried and evaporated to dryness. 0.450 g tert-butyl 4-(4-chloro-3-cyanophenyl)-piperazine-1-carbamidate are obtained as an oil. The product obtained and 2 ml trifluoroacetic acid are suspended in 3 ml dichloromethane. The reaction mixture is stirred at ambient temperature until no further reaction takes place and then evaporated to dryness. The residue is suspended in diethyl ether and the solid is suction filtered. 0.300 g (V-1) are obtained as the trifluoroacetate. Analytical HPLC-MS (method B): RT=1.02 min

The synthetic route of 57381-44-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/28441; (2011); A1;,
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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;,
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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;,
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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;,
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Reference of 2112-22-3,Some common heterocyclic compound, 2112-22-3, name is 2,3-Dichloro-6-nitrobenzonitrile, molecular formula is C7H2Cl2N2O2, 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.

2,3-dichloro-6-nitrobenzonitrile, 500 gm, was dissolved in 7500 ml of THF in a clean dry RB flask maintaining a nitrogen blanket. 139.3 am of sodium borohydride was added at 25-30 C. The suspension was cooled to 15-20 C. 653 gms of Borontrifluoride etherate was added to the reaction mixture over a period of about 2 hours while maintaining the temperature between 15-30 C. After the addition was complete, the temperature was raised about 65 C. and maintained at reflux for 2 hours. The reaction mixture was cooled to about 0-5 C. A mixture of 2.0 liter water and 200 ml concentrated HCl was slowly added to the reaction mixture while maintaining the temperature below 20 C. After the addition was complete, THF was distilled from the reaction mixture under vacuum maintaining temperature below 50 C. The reaction mixture was cooled to about 10-15 C. and 2.0 liter ethylacetate was added. The pH of reaction mixture was adjusted to 10-11 using 25% aqueous sodium hydroxide solution while maintaining the temperature below 15 C. The ethylacetate layer was separated and concentrated to about half the original volume. The reaction mixture was cooled to 15-20 C. and 500 ml IPA-HC1 was added slowly, maintaining temperature below 30 C. After cooling to about 0-5 C., the solids obtained were filtered and washed with 500 ml chilled ethylacetate. The solids were dried to obtain 2,3-dichloro-6-nitrobenzyl amine hydrochloride (450 gms),

The synthetic route of 2112-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WATSON PHARMA PRIVATE LIMITED; US2010/305318; (2010); A1;,
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51655-39-1, name is 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile, 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. Quality Control of 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile

Example 7 3-(ETHOXY-HYDROXY-METHYLENE)-5,6-DIMETHOXY-3H-INDENE-1-CARBONITRILE, SODIUM SALT A solution of tricyclohexylphosphine (82.0 mg, 0.293 mmol) in ethylene glycol dimethyl ether (10 mL) under nitrogen was charged with palladium (II) acetate (43.7 mg, 0.195 mmol). The reaction was stirred at room temperature until the solution was homogeneous (approx. 15 minutes) and stirred an additional 5 minutes before cooling to 0 C. and charging with sodium tert-butoxide (996 mg, 9.75 mmol). After 5 minutes a solution of 2-bromo-4,5-dimethoxyphenylacetonitrile (1.00 g, 3.90 mmol) and ethyl-3-ethoxyacrylate (0.564 ml, 3.90 mmol) in ethylene glycol dimethyl ether (5 ml) was added dropwise over 10 minutes. Upon complete addition the reaction mixture was warmed to room temperature and then heated to 85 C. for 16 hours. The reaction was cooled to room temperature then diluted with methyl tert-butyl ether (50 mL) and poured into aqueous potassium dihydrogenphosphate (0.25 M, 100 mL). The aqueous layer was separated and solid sodium chloride was added to the aqueous layer until saturated. The aqueous layer was extracted with ethyl acetate (1*125 mL) and this organic layer was washed with aqueous saturated sodium chloride 12*35 ml), dried over sodium sulfate, filtered and concentrated in vacuo affording 3-(ethoxy-hydroxy-methylene)-5,6-dimethoxy-3H-indene-1-carbonitrile, sodium salt, as a dark brown oil (906 mg, 3.3 mmol, 85 %) which crystallized on standing. 1H NMR (400 MHz, d4-MeOH) delta7.64 (s, 1H), 7.46 (s, 1H), 6.99 (s, 1H), 4.56 (q, 2H, J=7.1), 3.86 (s, 6H), 1.38 (t, 3H, J=7.05); 13C NMR (100 MHz,d4-MeOH) delta167.8, 145.0, 144.5, 130.2, 129.4, 126.4, 123.3, 112.5, 104.0, 102.6, 100.7, 79.0, 58.4, 55.6, 14.1; IR (ATR, neat) 3499, 2164, 1629, 1482, 1449, 1282, 1207, 1157, 1124, 1076, 845, 769 cm-1.

The synthetic route of 51655-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Singer, Robert A.; US2003/60624; (2003); 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. 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;,
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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;,
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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 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;,
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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;,
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