Category: 175596-01-7

Adding a certain compound to certain chemical reactions, such as: 175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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 175596-01-7, Product Details of 175596-01-7

EXAMPLE 20B methyl 2-fluoro-4-formylbenzoate EXAMPLE 20A (310 mg, 1.73 mmol) was dissolved in 60% aqueous acetic acid (10 mL) with warming. Raney nickel (60 mg) was added and the mixture was stirred under hydrogen at ambient temperature for 18 hours. Solid material was filtered off and the filtrate concentrated. The residue was purified on silica gel using 1:4 ethyl acetate/hexane to give the title compound (220 mg, 70%). MS (DCI): m/z 183 (M+H)+.

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Reference:
Patent; Penning, Thomas D.; Thomas, Sheela A.; Zhu, Gui-Dong; Gong, Jianchun; Giranda, Vincent L.; Gandhi, Viraj B.; US2007/112047; (2007); A1;,
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 175596-01-7 as follows. Recommanded Product: 175596-01-7

Preparation 91 4-Aminomethyl-2-fluoro-benzoic acid methyl ester Add a slurry of Raney nickel in ethanol (1.2 g, 1.2 ml) to 4-cyano-2-fluoro-benzoic acid methyl ester (5.8 g, 30.0 mmol) in 2N ammonia in methanol (580 mL). Purge with nitrogen gas (3*), purge with hydrogen gas (3*), and pressurize with hydrogen gas to 419 KPa. Heat the reaction at 40 C. for 18 hrs. Allow to cool to room temperature and filter the reaction mixture. Concentrate the filtrate to the crude title compound (6.9 g, 99%). MS (m/z): 184 (M+1).

According to the analysis of related databases, 175596-01-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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: 175596-01-7

Step (ii) Raney nickel (2.0 g) was added to a solution of methyl 4-cyano-2-fluorobenzoate (obtained as described in step (i) above) (10.1 g, 61.6 mmol) in acetic acid (200 ml.) and water (100 niL). The mixture was stirred at RT under argon at 20 bar. After 18 h the mixture was filtered through diatomaceous earth, washing through with water (1000 mL). The filtrate was extracted with EtOAc (3 chi 300 mL). The combined organic phases were dried and concentrated, adding toluene to assist removal of acetic acid, to give methyl 2- 11 uoro-4-( hydroxy meth) l)benzoate (crude, 6.06 g) which was used in the next step without further purification or characterisation.

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LIMITED; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; WO2015/25164; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 175596-01-7, These common heterocyclic compound, 175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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.

A sodium hydrogensulfide hydrate (9.22 g, 0.165 mol) was added to an N,N-dimethylformamide (74 mL) suspension of methyl 4-cyano-2-fluorobenzoate () (7.37 g, 41.1 mmol) and magnesium chloride hexahydrate (10.0 g, 49.4 mmol) at room temperature. The mixture was stirred at room temperature for 4 hours. Subsequently, water (148 mL) was added to the reaction mixture, and the precipitated solid was filtered. The solid thus obtained was added to 1 N aqueous hydrochloric acid solution (148 mL), and the mixture was stirred for 20 minutes. The solid in the reaction mixture was filtered to give the title compound (7.63 g, yield: 87%). 1H-NMR (500 MHz, DMSO-d6) delta ppm: 10.21 (1H, s), 9.75 (1H, s), 7.94-7.90 (1H, m), 7.79-7.72 (2H, m), 3.88-3.87 (3H, m).

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daiichi Sankyo Company, Limited; YAMANOI, Shigeo; NAMIKI, Hidenori; OCHIAI, Yuichi; HOSHINO, Madoka; MATSUMOTO, Koji; EP2805941; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 175596-01-7

A mixture of methyl 4-cyano-2-fluorobenzoate (2) (1 .0 g, 5.6 mmol) and 50% (0607) aq. hydroxylamine (6.84 mL, 1 12 mmol) in EtOH (30 mL) was stirred at reflux for 18 h. The reaction mixture was cooled to RT, diluted with H20 (20 mL) and extracted with EtOAc (60 mL). The organic solution was washed with brine (100 mL), dried over MgS04, filtered and concentrated in vacuo to give methyl 2-fluoro-4-(//’- hydroxycarbamimidoyl) benzoate (3) (260 mg, 22%) as a 1 :1 mixture of methyl and ethyl esters that was progressed without purification: m/z 227, 213 [M+H]+ (ES+)

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; BORTHWICK, Alan David; MILLS, Mark Trevor; BROWN, Jane Theresa; CORCORAN, Jonathan Patrick Thomas; DE CASTRO VASCONCELOS GONCALVES, Maria Beatriz; KALINDJIAN, Sarkis Barret; (161 pag.)WO2016/97004; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, A new synthetic method of this compound is introduced below., COA of Formula: C9H6FNO2

Step 2: methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate To a solution of methyl 4-cyano-2-fluorobenzoate, obtained in Step 1 (486.8 mg; 2.72 mmol) in abs. EtOH (6 ml_) was added hydroxylamine (0.8 ml 13.6 mmol; 5 eq.) (50% in water) and the mixture was heated at 74C overnight. After cooling, a product precipitated. The precipitate was filtered off and dried under vacuum to afford Intermediate 1 as an off-white solid (267.10 mg; 46%). 1H-NMR (DMSO-d6, 300MHz) delta 10.09 (s, 1 H), 7.92 (t, J = 7.91 Hz, 1 H), 7.69 (dd, J = 1.70 Hz, J = 8.10 Hz, 1 H), 7.64 (dd, J = 1.51 , J = 12.81 , 1 H), 6.05 (s, 2H), 3.90 (s, 3H). HPLC (Method B) Rt 2.99 min (Purity: 100%).

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.