Tag: M.W=100-200

Some common heterocyclic compound, 859855-53-1, name is 3-Amino-4-fluorobenzonitrile, molecular formula is C7H5FN2, 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. Application In Synthesis of 3-Amino-4-fluorobenzonitrile

Intermediate 28: (4-Fluoro-3-(pyrrolidin-l-yl)phenyl)methanamineStep 1: 4-Fluoro-3-(pyrrolidin-l-yl)benzonitrile3-Amino-4-fluorobenzonitrile (0.5 g, 3.67 mmol), 1 ,4-dibromobutane (0.439 ml, 3.67 mmol), sodium carbonate (0.779 g, 7.35 mmol) and toluene (3 ml) were added into a microwave vial. The resulting mixture was heated by microwave irradiation at 140 C for 2 hours. 1 ,4-dibromobutane (0.5 ml, 4.18 mmol) was added and the reaction mixture was irradiated at 140 C and at 160 C until the reaction had clearly stopped. The reaction mixture was diluted with dichloromethane and washed twice with water. The organic phase was dried over Na2S04, filtered and evaporated. The crude product was purified by column chromatography. 0.221 g of the title compound was obtained. NMR (400 MHz, CDC13) delta ppm 1.96 – 2.00 (m, 4 H) 3.39 – 3.48 (m, 4 H) 6.84 (dd, 1 H) 6.89 – 6.94 (m, 1 H) 6.96 – 7.04 (m, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 859855-53-1, its application will become more common.

Reference:
Patent; ORION CORPORATION; ARVELA, Riina; HOLM, Patrik; PIETIKAeINEN, Pekka; ROSLUND, Mattias; VAeISAeNEN, Emilia; WOHLFAHRT, Gerd; WO2012/152983; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, 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 34662-24-3, Quality Control of 2-Chloro-3-nitrobenzonitrile

A solution of anhydrous EtOH (20 mL) was bubbled through NH3 at 0C to obtain 7M NH3/EtOH. It was transfered intoa sealed tube containing 2-chloro-3-nitrobenzonitrile (0.5 g, 2.7 mmol, 1.0 eq). The mixture was allowed to warm to 18C gradually and then stirred at 110C for 12 hours. The mixture was evaporated under reduced pressure to remove the most solvent to give 0.5 g of crude 2- amino-3-nitrobenzonitrile as a yellow solid which was used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
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Some common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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. Quality Control of 5-Fluoro-2-nitrobenzonitrile

[0593] (a) Preparation of 5-[((2S)-1-methylpyrrolidin-2-yl)methoxy]-2-nitrobenzenecarbonitrile. To a slurry of 60% NaH (956 mg, 24 mmol) in THF (100 mL) was added (S)-(-)-1-methyl-2-pyrolidinemethanol (Aldrich) (2.8 mL, 24 mmol) resulting in gas evolution. After 30 min, 5-fluoro-2-nitrobenzonitrile (Combi Blocks) (3.3 g, 20 mmol) was added. After 3 h the reaction solvent was removed in vacuo and the residue was partitioned between CH2Cl2 and H2O. The aqueous layer was extracted with CH2Cl2 and the combined organics were dried over Na2SO4 and concentrated in vacuo to give a red oil. MS m/z: 262 (M+1). Calc’d for C13H15N3O3-261.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50594-78-0, its application will become more common.

Reference:
Patent; Huang, Qi; Kaller, Matthew; Nguyen, Thomas; Norman, Mark H.; Rzasa, Robert; Wang, Hui-Ling; Zhong, Wenge; US2003/229068; (2003); A1;,
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Application of 4421-09-4, 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. 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Description 2: (Z)-N’ -hydroxybenzo[d][l,3]dioxole-5-carboximidamide To a solution of benzo[d][l,3]dioxole-5-carbonitrile (15 g, 102 mmol), hydroxylamine hydrochloride (14.17 g, 204 mmol) in Ethanol (500 mL) was added Na2C03 (54.0 g, 510 mmol) in one charge. The reaction mixture was stirred at 80C for 5 hr. Then the solvent was removed under reduced pressure, the residual was washed with DCM (1L><4), filtered and the combined filtrate was concentrated under reduced pressure to afford (Z)-N'-hydroxy benzo[d][l,3]dioxole-5-carboximidamide as a yellow solid (15 g, 73.5%). MS(ES+) m/z 181.1 (MH+). The synthetic route of 3,4-(Methylenedioxy)benzonitrile has been constantly updated, and we look forward to future research findings. Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; WANG, Rong; LU, Hongtao; WO2013/107336; (2013); A1;,
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Some common heterocyclic compound, 10412-93-8, name is N-Benzyl-2-cyanoacetamide, molecular formula is C10H10N2O, 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. Product Details of 10412-93-8

General procedure: (E)–aryl–cyanoacrylamides 2 was prepared according to literature procedure.2 General procedure for 2a. To a solution of benzaldehyde (10 mmol 1.0 equiv), pyrrolidine (2 mmol, 20 mol %) in ethanol (20 mL) was added N-benzyl-2-cyanoacetamide (10 mmol, 1.0 equiv). The reaction mixture was stirred at room temperature until the reaction was complete (monitored by TLC), the solvent was removed under reduced pressure. The crude reaction mixture was purified through flash column chromatography on silica gel to afford 2a. 1H NMR (CDCl3, 400 MHz): delta (ppm) 8.68 (s, 1H), 7.78-7.74 (m, 1H), 7.70 (dd, J = 7.6, 1.4 Hz, 1H), 7.43 (t, J = 7.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz): delta (ppm) 167.9, 154.4, 137.8, 131.0, 126.4, 118.8, 115.6.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10412-93-8, its application will become more common.

Reference:
Article; Nie, Xufeng; Wang, Yachuan; Yang, Lijun; Yang, Zaijun; Kang, Tairan; Tetrahedron Letters; vol. 58; 31; (2017); p. 3003 – 3007;,
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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 6574-97-6 as follows. Recommanded Product: 6574-97-6

EXAMPLE 56C 3-Amino-2-carbomethoxy-7-chloro-benzthiophene The product from Example 56B (1.7 g, 10 mmol) was treated with 1 eq of methyl thioglycolate and 1 eq sodium carbonate in methanol as described in Example 41A to give after chromatography (4:1 hexane/EtOAc) the title compound in 12percent yield. 1H NMR (300 MHz, CDCl3) d 3.81 (s, 3H), 5.90 (bs, 2H), 7.34 (t, J=8 Hz, 1H), 7.48 (dd, J=8.1 Hz, 1H), 7.56 (dd, J=8,1 Hz, 1H). MS (DCI/NH3) m/e 259 (M+NH4)+.

According to the analysis of related databases, 6574-97-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbott Laboratories; US5597823; (1997); A;,
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Application of 21803-75-8, The chemical industry reduces the impact on the environment during synthesis 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

Thionylchloride (15 mL) was dropped into water (60 mL) with stirring and cooling sothat the temperature did not rise above -5C. Copper(I) chloride (19 mg) wasthen added. In parallel, 4-amino-3-chlorobenzonitrile (1.50g, 9.83 mmol) wasdissolved in cone. HCl (30 mL), cooled to -5C whereupon a solution of sodiumnitrite (746 mg, 10.8 mmol) in water (15 mL) was added . After completeaddition the solution of diazonium salt was added in over 2 mins to the firstsolution, both at -5 to OoC (gas evolution was observed) and a foam formed ontop of the solution. The temperature was allowed to come to room temperatureand the aqueous phase was then extracted with DCM (3 x 70 ml). The combinedorganic phase was washed with brine (5 mL), dried (Na2SC>4), themixture filtered and the filtrate evaporated to dryness to afford a yellowsolid containing the title compound (1.88 g, 88%); ‘H NMR (500 MHz, CDC13)delta 7.83 (dd, IH), 7.97 (d, IH), 8.31 (d, IH).

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, 4-Amino-3-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, 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 621-50-1, Quality Control of 2-(3-Nitrophenyl)acetonitrile

(3-Nitro-phenyl)-acetonitrile (1.51 g, 9.31 mmol), dimethoxymethyl-dimethyl-andine (6.2 mL, 46.5 mmol) in xylene (30 mL) are stirred at reflux for 1 hour. After adding hexane (20 mL), the reaction mixture is cooled at 0C. Precipitating material is filtered-off to give compound of Stage 52.1 as brown solid (1.76 g, 8.19 mmol ; 88%); ES-MS: M+H = 218. 1; HPLC: tRet = 2.24 minutes. 1H-NMR (300 MHz, DMSO-d6) : 8.10-8. 05 (m, 1H), 7.90-7. 85 (m, 1H), 7.75-7. 72 (m, 1H), 7.70 (s, 1H), 7.65-7. 60 (m, 1H), 3.30 (s, 6H).

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-(3-Nitrophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/70431; (2005); A1;,
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Synthetic Route of 874-89-5,Some common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, 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: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data.

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

Reference:
Article; Farhadi, Saeed; Jahanara, Kosar; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 3; (2014); p. 368 – 375;,
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Electric Literature of 198633-76-0,Some common heterocyclic compound, 198633-76-0, name is 2-Fluoro-6-methylbenzonitrile, molecular formula is C8H6FN, 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.

Step A: 3-bromo-6-fluoro-2-methylbenzonitrile (Method A): Commercially available 2-fluoro-6-methylbenzonitrile (Apollo Scientific, 15.0 g, Ill mmol) was dissolved in triflic acid (75 mL)at 0 C then NBS (20.7 g, 117 mmol) was added. The reaction mixture was stirred at RT for 1 hthen poured into ice water and extracted twice with DCM. The organic layer was washed with brine, dried over Na2S04, then filtered and evaporated to dryness to yield 3-bromo-6-fluoro-2-methylbenzonitrile: LC-MS: M+ 1 = 214, 216.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-6-methylbenzonitrile, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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