Category: 6393-40-4

Application 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.

Step 1 3,4-Diaminobenzonitrile 2-Nitro-4-cyanoaniline (2.21 g) was hydrogenated using 7.5% palladium carbon (320 mg) in ethanol (44 ml) at atmospheric pressure over 2 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. To the obtained residue was added chloroform and the resultant solid was collected by filtration and dried under reduced pressure to give the title compound (474 mg). 1H-NMR (delta ppm, DMSO-d6) 4.82-4.85 (2H), 5.41-5.43 (2H), 6.54 (d, J=8.1 Hz, 1H), 6.75 (d, J=2.1 Hz, 1H), 6.79 (dd, J=2.1, 8.1 Hz, 1H).

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:
Patent; Japan Tobacco Inc.; US6562828; (2003); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products 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.

Reduction of the nitro group with 10% Pd-C in Par hydrogenator afforded 2-amino-4-cyanoaniline in 85% yield.

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:
Patent; University of North Carolina; US5428051; (1995); A;,
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.

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).

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

Reference:
Patent; PHARMACOPEIA , INC.; WO2008/60301; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6393-40-4, name is 4-Amino-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 6393-40-4, Recommanded Product: 6393-40-4

General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

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:
Article; Go, Ahra; Lee, Geunsoo; Kim, Jaeho; Bae, Seolhee; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 71; 8; (2015); p. 1215 – 1226;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

6393-40-4, 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 6393-40-4 as follows.

A sample of 2 (6.13 mmol) was suspended in 55 mL ofdry methanol and the suspension was saturated with HCl(g)for 30 min. After 4 days stirring at room temperature, thesuspension was filtrated and the solid was washed with120 mL of ethyl ether. The yellow solid obtained wasdissolved in dry methanol and saturated with NH3 during6 h. The solution was concentrated to half and to theresulting solution was added 60 mL of ethyl ether. Theresulting precipitated was collected by filtration and washedwith 50 mL of ethyl acetate, affording the interest product. 4-Amino-3-nitrobenzamidine hydrochloride (3) This product was obtained as a yellow solid (60%yield); mp > 300 C; IR (ATR) nu / cm-1 3453, 3420 (NH2),3134, 3052 (NH.HCl amidine), 1685 (C=N), 1628 (NH2);1H NMR (200 MHz, DMSO-d6) delta 9.38 (br s, 2H, Hamidine), 9.12 (br s, 2H, H amidine), 8.62 (s, 1H, H arom.),8.17 (s, 2H, NH2), 7.87 (d, J 9.0 Hz, 1H, H arom.), 7.19 (d,J 9.0 Hz, 1H, H arom.); 13C NMR (50 MHz, DMSO-d6) delta 163.5, 149.1, 133.6, 129.6, 127.6, 119.4, 113.2.

According to the analysis of related databases, 6393-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; de Souza, Thiago B.; Oliver, Josidel C.; Gomes, Ana Paula B.; Aragao, Cicero Flavio S.; Ferreira, Leandro S.; Nogueira, Fernando Henrique A.; Dias, Amanda Latercia T.; Alves, Ricardo J.; Journal of the Brazilian Chemical Society; vol. 29; 6; (2018); p. 1304 – 1317;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

6393-40-4, 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.

General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

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:
Article; Go, Ahra; Lee, Geunsoo; Kim, Jaeho; Bae, Seolhee; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 71; 8; (2015); p. 1215 – 1226;,
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 6393-40-4 as follows. 6393-40-4

A sample of 2 (6.13 mmol) was suspended in 55 mL ofdry methanol and the suspension was saturated with HCl(g) for 30 min. After 4 days stirring at room temperature, thesuspension was filtrated and the solid was washed with120 mL of ethyl ether. The yellow solid obtained wasdissolved in dry methanol and to this solution was added1 mL of isopropylamine; the mixture was heated underreflux for 3 h. The solvent was removed and the solidresulting was washed with 150 mL of ethyl ether and120 mL of ethyl acetate. 4-Amino-3-nitro-N-isopropylbenzamidine hydrochloride (5) This product was obtained as a yellow solid (63% yield);mp 259.5-261.6 C; IR (ATR) nu / cm-1 3456, 3161 (NH2),3047, 2942 (NH.HCl amidine), 1685 (C=N); 1H NMR(200 MHz, DMSO-d6) delta 8.44 (br s, 1H, H arom.), 8.08(br s, 2H, NH2), 7.76 (br s, 1H, H arom.), 7.20 (br s, 1H,H arom.), 4.07 (m, 1H, CH), 1.23 (d, J 5.6 Hz, 6H, CH3);13C NMR (50 MHz, DMSO-d6) delta 159.5, 148.6, 134.2,129.3, 127.2, 119.2, 115.5, 44.9, 21.5.

According to the analysis of related databases, 6393-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; de Souza, Thiago B.; Oliver, Josidel C.; Gomes, Ana Paula B.; Aragao, Cicero Flavio S.; Ferreira, Leandro S.; Nogueira, Fernando Henrique A.; Dias, Amanda Latercia T.; Alves, Ricardo J.; Journal of the Brazilian Chemical Society; vol. 29; 6; (2018); p. 1304 – 1317;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

To a stirred solution of 4-amino-3-nitro-benzonitrile (2.00 g, 12.3 mmol) in methanol (20 mL) was added Pd/C (500 mg, 10% purity), then the flask was degassed and filled with hydrogen three times, and the reaction mixture stirred vigorously under hydrogen (balloon) for 18 h at 25 C. The mixture wasevacuated and backfilled with nitrogen three times, then filtered through a pad of celite, and the filtrate concentrated in vacuo to give 3,4-diaminobenzonitrile (1 .47 g, 11 .04 mmol, 90 %) as a green oil that was used in next step directly.

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; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); 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 6393-40-4 as follows. 6393-40-4

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.

According to the analysis of related databases, 6393-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACYCLICS, INC.; Dickman, Daniel A.; Kumar, Dange Vijay; O’Bryan, Colin; Rai, Roopa; Shrader, William Dvorak; US2014/80879; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

6393-40-4, Name is 4-Amino-3-nitrobenzonitrile, 6393-40-4, 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.

General procedure: GeneralProcedure for the preparation of 2-Phenyl-1H-benzoimidazole (3aa): A 25mL over-dried Schlenk tube was charged with 2-nitroaniline (41.4 mg, 0.3 mmol),benzyl alcohol (97.2 mg, 0.90 mmol) and Pd(dppf)Cl2 (12.2 mg, 0.015mmol). The tube was purged with nitrogen three times. Toluene (1 mL) was addedto the sealed reaction vessel by syringe. The reaction mixture was stirred in apreheated oil bath at 160 oC for 24 h. After cooling to roomtemperature, the reaction mixture was then concentrated in vacuo, and theresidue was purified by column chromatography (silica gel, petroleumether/ ethyl acetate = 4:1) to give 3aa as a pale yellow solid (56.5 mg, 97%).

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

Reference:
Article; Li, Xiaotong; Hu, Renhe; Tong, Yao; Pan, Qiang; Miao, Dazhuang; Han, Shiqing; Tetrahedron Letters; vol. 57; 41; (2016); p. 4645 – 4649;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts