Category: 159847-81-1

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 159847-81-1 as follows. Product Details of 159847-81-1

2-amino-5-cyanobenzoic acid. To a solution of methyl 2-amino-5- cyanobenzoate (0.120 g, 0.68 mmol) in THF (3.5 ml), was added a solution of lithium hydroxide (0.033 g, 1.36 mol, 2.0 eq) in H20 (3.5 ml). After stirring at rt for 3h, the reaction mixture was concentrated. The residue was diluted with H20 (5 ml) and acidified to pH~3 using 1M HCl. The precipitate was collected by filtration, washed with H20 and dried under air. 2-amino-5-cyanobenzoic acid (0.11 g, 95%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-de) delta 8.04 (d, J= 2.1 Hz, 1H), 7.70-7.33 (m, 3H), 6.86 (d, J= 8.8 Hz, 1H).

According to the analysis of related databases, 159847-81-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF KANSAS; UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.; SOUTHERN RESEARCH INSTITUTE; GOLDEN, Jennifer; AUBE, Jeffrey; CHUNG, Donghoon; SCHROEDER, Chad; YAO, Tuanli; WHITE, E. Lucile; TOWER, Nichole A.; WO2014/93869; (2014); 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. 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H8N2O2

To a suspension of 3- (chlorosulfonyl) benzoic acid (10.8 g, 49.0 mmol) in CH2Cl2 (105 mL) and three drops [OF DMF] was added oxalyl chloride (12.5 mL) and the reaction was stirred at rt overnight. The solution was concentrated in vacuo, diluted with [CH2C12] (100 mL), and the solution was divided into two reactions. A 50 mL (24.5 mmol) aliquot of the acid chloride was added to a solution of PHA-522499 (4.49 g, 25.5 mmol) dissolved in [CH2C12] (50 mL) and pyridine (3.0 [ML)] and stirred at rt overnight. The solution was diluted with MTBE, washed with 2 N HC1 and brine, concentrated, [TRITURATED WITH MTBE] to afford 7.91 g [(85%)] of methyl [2-{[3-] (chlorosulfonyl) benzoyl] [AMINO}-5-CYANOBENZOATE] as a tan [SOLID. 1H NMR (400 MHZ,] [DMSO-D6)] [8] 11.73 (s, 1 H), 8.67 (d, [J=] 9 Hz, [1] H), 8.37 (d, [J=] 2 Hz, 1 H), 8.25 (s, 1 H), 8.12 (dd, J= 9,2 Hz, 1 H), 7.92 (d, J= 8 Hz, [1] H), 7. [88] (d, J= 8 Hz, 1 H), 7.60 (t, [J= 8 HZ, 1 H),] 3.93 (s, 3H).

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 159847-81-1.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 159847-81-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 159847-81-1 name is Methyl 2-amino-5-cyanobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Methyl [2-AMINO-5-CYANOBENZOATE] (5.0 g, 28.41 mmol) was dissolved in MeOH (105 mL). Then 6M [NAOH] (14 mL) was added. The resulting mixture was stirred at RT O/N. The reaction mixture was diluted with H20 (143 mL), washed with DCM to remove any unreacted S. M. The product was precipitated from aqueous layer by addition of conc. [HC1] to pH 1 and extracted with EtOAc (3 x 100 mL). The combined organic layers were dried over MgS04 Solid was removed by filtration, and filtrate was concentrated to dryness under reduced pressure. The light yellow product was obtained in the yield of 94%. [‘H NMR] (300 MHz, DMSO-d6) 8 8.08 (d, 1H), 7.56 (dd, [1H),] 7.50 (br), 6.85 (d, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-5-cyanobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18428; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 159847-81-1, 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. 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 2,4-dichloro-6-cyanoquinoline-3-carboxylate, 13 [00167] To a solution of methyl 2-amino-5-cyanobenzoate (5.68 mmol) in DCM (lOmL) was added triethyamine (8.52 mmol) followed by methyl 3-chloro-3-oxopropionate (7.38 mmol). The resulting reaction mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between EtOAc and 1M HCl and the layers then separated. The organic layer washed sequentially with saturated aqueous NaHC03 followed by brine. The organic layer was dried over Na2S04, filtered, and concentrated in vacuo. The resulting residue was carried on without further purification. [00168] The residue from above was treated with 0.5M NaOMe in MeOH (6.83 mmol). The heterogenous mixture was stirred at ambient temperature for 30 min. Diethyl ether was then added to the reaction mixture and the solid was collected via vacuum filtration, washing with ether. The obtained solid was carried on without further purification. [00169] To a flask containing the solid from above cooled to 0 C was added POCI3 (15 mL). The mixture became warm and bubbled. The resulting reaction mixture was heated to 90C for 3 h. Cooled the dark reaction mixture to ambient temperature and poured it very slowly into stirring saturated aqueous NaHC03 cooled to 0 C. Solid NaHC03 was then added until the solution was basic. The aqueous solution was extracted with EtOAc (3x). The combined organic layers were dried over Na2S04, filtered, and concentrated in vacuo. The obtained residue was purified via flash column chromatography, eluting with 9: l/hexanes:EtOAc, to yield the intermediate 13 (29% over 3 steps). M S ESI (tn/z) 281 Cvl Pi } . FontWeight=”Bold” FontSize=”10″ B NMR (300 MHz, CDCK) delta 8.63 (d, I B, J l .K Hz), 8.16 (d, 1H, J=8.4 Hz), 8.00 (dd, 1H, J=L8, J2=SA Hz), 4.08 (s, 3H); 13C NMR (CDCI3, 75MHz) 6 163.4, 148.9, 148.1 , 141 .8, 133.3, 1 30.8, 130.6, 128.8, 124.3, 1 1 7.7, 1 12.8, 54.1 .

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-amino-5-cyanobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; FIORITO, Jole; ARANCIO, Ottavio; WASMUTH, Andrew; WO2015/9930; (2015); 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 159847-81-1 as follows. category: nitriles-buliding-blocks

2-amino-5-cyanobenzoic acid. To a solution of methyl 2-amino-5- cyanobenzoate (0.120 g, 0.68 mmol) in THF (3.5 ml), was added a solution of lithium hydroxide (0.033 g, 1.36 mol, 2.0 eq) in H20 (3.5 ml). After stirring at rt for 3h, the reaction mixture was concentrated. The residue was diluted with H20 (5 ml) and acidified to pH~3 using 1M HCl. The precipitate was collected by filtration, washed with H20 and dried under air. 2-amino-5-cyanobenzoic acid (0.11 g, 95%) was obtained as a white solid. 1H NMR (400 MHz, DMSO-de) delta 8.04 (d, J= 2.1 Hz, 1H), 7.70-7.33 (m, 3H), 6.86 (d, J= 8.8 Hz, 1H).

According to the analysis of related databases, 159847-81-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF KANSAS; UNIVERSITY OF LOUISVILLE RESEARCH FOUNDATION, INC.; SOUTHERN RESEARCH INSTITUTE; GOLDEN, Jennifer; AUBE, Jeffrey; CHUNG, Donghoon; SCHROEDER, Chad; YAO, Tuanli; WHITE, E. Lucile; TOWER, Nichole A.; WO2014/93869; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 159847-81-1,Some common heterocyclic compound, 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, molecular formula is C9H8N2O2, 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 solution of methyl 2-amino-5-cyanobenzoate (5.68 mmol) in DCM (lOmL) was added triethyamine (8.52 mmol) followed by methyl 3-chloro-3-oxopropionate (7.38 mmol). The resulting reaction mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between EtOAc and IM HCI and the layers then separated. The organic layer washed sequentially with saturated aqueous NaHCO, followed by brine. The organic layer was diied over Na2S04, filtered, and concentrated in vacuo. The resulting residue was carried on without further purification. [00170] The residue from above was treated with 0.5M NaOMe in MeOH (6.83 mmol). The heterogenous mixture was stirred at ambient temperature for 30 min. Diethyl ether was then added to the reaction mixture and the solid was collected via vacuum filtration, washing with ether. The obtained solid was carried on without further purification. [00171] To a flask containing the solid from above cooled to 0 C was added POCK (15 mL). The mixture became warm and bubbled. The resulting reaction mixture was heated to 90C for 3 h. Cooled the dark reaction mixture to ambient temperature and poured it very slowly into stirring saturated aqueous NaHCOj cooled to 0 C. Solid NaHCQs was then added until the solution was basic. The aqueous solution was extracted with EtOAc (3x). The combined organic layers were dried over a2S04, filtered, and concentrated in vacuo. The obtained residue was purified via flash column chromatography, eluting with 9: l/hexanes:EtOAc, to yield the intermediate 13 (29% over 3 steps). MS ESI (m/z) 281 (M+ J ); ;H NMR (300 MHz, CDCi3) 5 8.63 (d, 1 H, J=l .8 Hz), 8.16 (d, 1H, ./ 8 · Hz), 8.00 (dd, lH, Hz), 4.08 (s, 3H); i C NMR (CDC , 75MHz) 5 163.4, 148.9, 148.1 , 141 .8, 1 33.3, 130.8, 130.6, 128.8, 124.3, 1 17.7, 1 12.8, 54.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-amino-5-cyanobenzoate, its application will become more common.

Electric Literature of 159847-81-1, 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 159847-81-1 as follows.

A mixture [OF 4- [ (5-chloro-2, 3-dihydro-1H-indol-1-yl) sulfonyl)] benzoic acid. (0.50 g, 1.49 mmol) and oxalyl chloride (5 mL) in CH2C12 (3mL) was treated with DMF (3 [, L)] and heated to [40 C. AFTER] 2h, the mixture was cooed and concentrated in vacuo to give a yellow semi-solid residue that was dissolved in CH2C12 (2 mL) and pipetted into a mixture of methyl [2-amino-5-cyanoBENZOATE] (0.25 g, 1.40 mmol) in pyridine (5 mL) at [5 C.] The mixture was allowed to stir at room temperature overnight and then concentrated in vacuo. The residue was dissolved in [CH2C12] and aqueous IN CHl.The phases were separated. The organic phase was washed with aqueous 1 N HCl, and H2O, dried [(NA2S04),] and concentrated in vacuo to provide a tan solid that was digested in hot ethanol. The cooled mixture was filtered. The solid was dried in a vacuum oven at [60 C] to give 0.42 g (61 %) of cream solid [PRODUCT. 1H] NMR (400 MHz, DMSO-d6) 8 2.95 (t, 2 H), 3.88 (s, 3 H), 4.01 (t, 2 H), 7.26 [(M,] 2 H), 7.49 (d, [1] H), 8. 12 [(M,] 5 H), 8.37 (s, 1 H), 8.53 (d, [1] H), 11.5 (s, 1 H); MS (ESI-) for [C24HL8CLN305S] [M/Z] 493.9 (M-H)-.

According to the analysis of related databases, 159847-81-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18461; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 159847-81-1, These common heterocyclic compound, 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, 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 mixture of A [(2. 0] g, 7.37 [MMOL),] oxalyl chloride (10 mL), and [CH2CL2] (4 mL) was treated with DMF (ca. [2GEL).] The mixture was stirred at room temperature for 1 hr and then heated to reflux for 5 h. The yellow solution was cooled and concentrated in vacuo to give crude acid chloride that was redissolved in [CH2C12] (2 mL) and added slowly to a mixture of methyl [2-amino-5-cyanobenzoate] (1.28 g, 7.37 mmol) in dry pyridine (10 mL). The red mixture was stirred at room temperature for lh and then heated to reflux for 3 h under N2. The reaction mixture was cooled to room temperature, diluted with H20 (2 mL), and concentrated in vacuo to a slurry mixture that was diluted with ethyl acetate. The mixture was filtered. The solids were washed with H20 and dried in a vacuum oven to give 2.02 g (64 % yield) of product: mp 184- [185 C] : MS (ESI+) for [C2OH19N306S] [M/Z] 429.9 [(M+H) +.] IR (diffuse reflectance) 3457,3362, 2224,1642, 1551,1485, 1401,1306, 1261,1178, 1156,900, 858, [821,] 634 [CM~L.] MS (CI) m/z [(REL.] intensity) 244 (M+, 0), 245 (12), 244 (99), 127 (9), 118 (9), 117 (72), 90 (75), 84 (11), 64 (14), 63 (42), 62 (13). Anal. Calcd for [C7HSIN2] : C, 34.45 ; H, 2.07 ; N, 11.48.Found: C, 34.57 ; H, 2.08 ; N, 11. 48.

Statistics shows that Methyl 2-amino-5-cyanobenzoate is playing an increasingly important role. we look forward to future research findings about 159847-81-1.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18461; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, 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 159847-81-1, Product Details of 159847-81-1

b. 5-Cyano-2-[2-(3-methyl-isoxazol-5-yl)-acetylamino]-benzoic acid methyl ester A solution of 2-amino-5-cyano-benzoic acid methyl ester (1. 50G, 8.51 mmol) and (3-methyl-isoxazol-5-yl) -acetic acid (1.32 g, 9.36 mmol) in 40 ml of POCl3 was heated at 80 C for 2 hr and then cooled to RT. Treated with 50 mL of EtOAc, the mixture was washed with H20 (3 x 40 ml), sat. NAHC03 (40 ml), brine (40 ml) and dried (NA2S04). Removal of the solvent under reduced pressure gave 2.31 g (91 %) of product as a light yellow solid : H-NMR (CDC13 ; 400 MHz) 8 11.49 (s, 1H), 8.85 (d, 1H, J = 8.8 Hz), 8.35 (d, 1H, J = 2. 0 Hz), 7.79 (dd, 1H, J = 8. 8,2. 0 Hz), 6.20 (s, 1H), 3.97 (s, 3H), 3.95 (s, 2H), 2.33 (s, 3H). Mass spectrum (ESI, m/z) : Calcd. for CLSHL3N3O4 300.1 (M+H), found 299.9.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2005/9967; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts