Category: 6393-40-4

Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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. category: nitriles-buliding-blocks

3-Nitro-4-aminobenzonitrile (3.00 g) was dissolved in ethanol (300 ml) and added with stannous chloride dihydrate (20.7 g) and the whole was heated to 60C. Sodium borohydride (348 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was added with water (300 ml) and neutralized with a 5 mol/l sodium hydroxide aqueous solution. After ethanol was distilled off under reduced pressure, the aqueous layer was added with ethyl acetate for extraction. The organic layer was washed with a saturated saline solution and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was recrystallized, thereby obtaining the subject compound (1.11 g) as a brown crystal. MS(EI):m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8,1Hz),6.95(1H,s),7.05(1H,d,J=8.1Hz).3-Nitro-4-amino-benzonitrile (4.38 g) was dissolved in ethanol (600 ml) and added with stannous chloride dihydrate (34.6 g) and the whole was heated to 60C. Sodium borohydride (366 mg) was gradually added thereto and the whole was stirred overnight at 60C. After completion of the reaction, the resultant was filtrated through Celite and the filtrate was subjected to distillation of the solvent under reduced pressure. The residue was dissolved in chloroform, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was allowed to recrystallize (hexane/ethyl acetate), thereby obtaining the subject compound (2.56 g) as a brown crystal. MS (EI) :m/z=133[M]+ 1H-NMR(500MHz,CDCl3):delta=6.68(1H,d,J=8.1Hz),6.95(1H,s),7.05(1H, d,J=8.1Hz).An ethanol solution (300 ml) containing 4-amino-3-nitrobenzonitrile (3.00 g) was added with stannous chloride dihydrate (20.7 g) and then added with sodium borohydride (348 mg) . The whole was stirred overnight at 60C. After that, the resultant was subjected to distillation until the amount of the solution became about 100 ml. The resultant was added with water (100 ml) and a large amount of solid component was generated. The resultant was added with a 5 mol/l sodium hydroxide aqueous solution (42 ml) to adjust to pH 7. The solvent was distilled off. The solid component was filtrated out through Celite and washed with methanol and ethyl acetate in the stated order. The filtrate was again filtrated through Celite and only organic solvent was distilled off under reduced pressure. The remaining aqueous layer was subjected to extraction with ethyl acetate and dried with anhydrous magnesium sulfate , and the solvent was distilled off, thereby obtaining the subject compound (2.29 g) as a khaki crystal.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6393-40-4, its application will become more common.

Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 6393-40-4, 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. 6393-40-4 name is 4-Amino-3-nitrobenzonitrile, 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.

General procedure: A 100-mL round-bottomed single-neck flask equipped with a condenser and a magnetic stir bar was charged with appropriated 4-substituted-2-nitroaniline (25.0mmol), 2,5-dimethoxytetrahydofurane (25.0mmol) and 40mL of glacial acetic acid. The flask was refluxed until disappearance of starting material (ca. 2 h). After the reaction mixture was cooled to rt, removal of the volatiles under reduced pressure gave the crude product which was purified by column-chromatography (Petroleum Ether/EtOAc=9:1 then 7:3) to give the desired 1-(4-substituted-2-nitrophenyl)-1H-pyrrole.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Primas, Nicolas; Suzanne, Peggy; Verhaeghe, Pierre; Hutter, Sebastien; Kieffer, Charline; Laget, Michele; Cohen, Anita; Broggi, Julie; Lancelot, Jean-Charles; Lesnard, Aurelien; Dallemagne, Patrick; Rathelot, Pascal; Rault, Sylvain; Vanelle, Patrice; Azas, Nadine; European Journal of Medicinal Chemistry; vol. 83; (2014); p. 26 – 35;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 6393-40-4, These common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, 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.

Reference B; Synthesis of 3,4-diaminobenzamidine monohydrochloride; Step 1; A mixture of 4-amino-3-nitrobenzonitrile (63.3 g, 388 mmol) in 1,4-dioxane (600 mL) and anhydrous ethanol (600 mL) was cooled in an ice water bath to 0-5 C and treated with gaseous HCl for 1.5 h. The reaction mixture was tightly sealed and allowed to warm up to room temperature with stirring for 18 h. The flask was then carefully unsealed and the reaction mixture was diluted with anhydrous diethyl ether (about 2.4 L) until a cloudy solution was obtained. A minimum amount of absolute ethanol required to give a clear solution was then added, and the resulting solution stirred until crystals of 4-amino-3-nitro-benzimidic acid ethyl ester were observed. Ether was then cautiously added to complete the crystallization process and the suspension was allowed to stand for about 30 minutes. The crystals were filtered and washed with dry diethyl ether, then allowed to dry under aspirator vacuum. The crystals were dried in vacuo to give 4-amino-3-nitro-benzimidic acid ethyl ester hydrochloride (84.6 g) as off-white crystals.

The synthetic route of 6393-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2005/118554; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 6393-40-4,Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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.

Example 1. Synthesis of 3,4-Diaminobenzonitrile[0082] A solution of 4-amino-3-nitrobenzonitrile (1) (3.0 g) in ethanol (80 mL) was sparged for 5 minutes with nitrogen. Palladium on carbon (10%, 300 mg) was added and the mixture was saturated with hydrogen. The mixture was stirred under a hydrogen balloon for seven hours. The mixture was sparged with nitrogen and filtered through celite. The filtrate was concentrated in vacuo to provide the title compound, 3,4- diaminobenzonitrile (2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-3-nitrobenzonitrile, its application will become more common.

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. 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

A solution of 4-amino-3-nitrobenzonitrile (1) (3.0 g) in ethanol (80 mL) was sparged for 5 minutes with nitrogen. Palladium on carbon (10%, 300 mg) was added and the mixture was saturated with hydrogen. The mixture was stirred under a hydrogen balloon for seven hours. The mixture was sparged with nitrogen and filtered through celite. The filtrate was concentrated in vacuo to provide the title compound, 3,4- diaminobenzonitrile (2).

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 6393-40-4.

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. 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Formula: C7H5N3O2

A mixture of 4-amino-3-nitrobenzonitrile (63.3 g, 388 mmol) in 1,4-dioxane (600 mL) and anhydrous ethanol (600 mL) was cooled in an ice water bath to 0-5 C and treated with gaseous HCl for 1.5 h. The reaction mixture was tightly sealed and allowed to warm up to room temperature with stirring for 18 h. The flask was then carefully unsealed and the reaction mixture was diluted with anhydrous diethyl ether (about 2.4 L) until a cloudy solution was obtained. A minimum amount of absolute ethanol required to give a clear solution was then added, and the resulting solution stirred until crystals of 4-amino-3-nitro- benzimidic acid ethyl ester were observed. Ether was then cautiously added to complete the crystallization process and the suspension was allowed to stand for about 30 minutes. The crystals were filtered and washed with dry diethyl ether, then allowed to dry under aspirator vacuum. The crystals were dried in vacuo to give 4-amino-3-nitro-benzimidic acid ethyl ester hydrochloride (84.6 g) as off-white crystals.

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.

Application of 6393-40-4, These common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, 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.

In DMF (20 ml), 3-nitro-4-aminobenzonitrile (1.12 g) was dissolved, and the solution was added with 60% sodium hydride (411 mg), followed by stirring at room temperature for 30 minutes. The solution was added with 1-iodopropane (805 mul) and stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in ethyl acetate. The resultant was washed with water and then subjected to extraction with ethyl acetate. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure, thereby obtaining a crude product (1.58 g) of the subject compound as a yellow solid. MS(FAB,Pos.):m/z=206[M+H]+

Statistics shows that 4-Amino-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 6393-40-4.

These common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, 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. COA of Formula: C7H5N3O2

In DMF (15 ml), 3-nitro-4-aminobenzonitrile (500 mg) was dissolved, and the solution was added with sodium hydride (135 mg), followed by stirring at room temperature for 9 hours. The solution was added with 1-iodopropane (328 ml) and stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then dissolved in chloroform. The solution was washed with water and then subjected to extraction with chloroform. The organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform), thereby obtaining the subject compound (362 mg) as a white solid. MS(FAB,Pos.):m/z=206[M+H]+ 1H-NMR(500MHz,CDCl3):delta=1.08(3H,t,J=7.6Hz),1.79(2H,sext.,J=7.3Hz),3.33(2H,q,J=7.1Hz),6.91(1H,d,J=9.0Hz),7.60(1H,d,J=9.0Hz),8. 43(1H,br),8.52(1H,s).

The synthetic route of 4-Amino-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

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. 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Amino-3-nitrobenzonitrile

General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

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.

Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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. Formula: C7H5N3O2

a) Preparation of 3,4 diamino benzonitrile 4-Amino 3-nitro-benzonitrile (5.0 g, 0.03 moles) was dissolved in ethyl acetate then treated with 2.5 g of 10% Pd/C. The reaction mixture was flushed with hydrogen and allowed to stir overnight at 23 C. The reaction was not quite complete so 0.5 g more 10% Pd/C was added. After 2 hours the reaction was complete. The solution was filtered through celite, concentrated and used without further purification (4.67 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6393-40-4, its application will become more common.

Reference:
Patent; SmithKline Beecham Corporation; US6133319; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts