Category: 32692-19-6

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6,Some common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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.

We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid. Mp: 177.0-178.1 C. 1H NMR (400 MHz, DMSO-d6): delta = 8.00 (1H, m), 7.86 (1H, s), 7.26 (4H, m), 6.70 (1H, d, J = 8.94 Hz), 5.71 (1H, s), 3.81 (1H, m), 3.21 (1H, m), 3.00 (2H, m), 2.32 (3H, s); 13C NMR (400 MHz, DMSO-d6): delta = 171.16, 156.59, 137.70, 137.38, 131.42, 130.49, 129.23, 128.83, 126.02, 120.28, 104.61, 61.16, 49.18, 26.15, 20.68 ppm. Calculated for C17H16N2O4, MS (ESI): m/z = 313.1181 (M+H)+.

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

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

A solution of 5-nitroindoline (1.033 g, 6.30 mmol), TEA (0.827g, 8.19 mmol) in DCM (30 mL) at 0C was slowly added methylsufonyl chloride (0.868 g, 7.56 mmol). The mixture was warmed up and stirred at room temperature for 0.5 h. The reaction was quenched with water (30 mL) and extracted with DCM (25 mL x4). The organic layers were combined, dried and concentrated under reduced pressure to afford crude 1 (1.427 g, 5.9 mmol, yield 95%), which was used for next step without further purification.

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.

Reference:
Patent; ACEA BIOSCIENCES INC.; XU, Xiao; WANG, Xiaobo; MAO, Long; ZHAO, Li; XI, Biao; WO2015/6754; (2015); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., name: 5-Nitroindoline

Example V; 5-nitro-1 -pyrimidin-2-yl-2,3-dihydro-1 H-indole300 mg 5-nitro-2,3-dihydro-1 H-indole are dissolved in 4 ml N-methyl- pyrrolidine. 80 mg NaH (60 % suspension in mineral oil) are added and the mixture is stirred for 15 minutes at ambient temperature. Then 380 mg of 2- bromopyrimidine are added and the mixture is then heated to 600C for 3 hours. It is then diluted with diethyl ether and washed with dilute citric acid solution and saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo. Yield: 410 mg (95 % of theory) Rf value: 0.61 (silica gel: ethyl acetate/petroleum ether 1 :1 )

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.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/16118; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H8N2O2

To a solution of 5-nitroindoline (11.72 g) and triethylamine (8.67 g) in N, N-dimethylformamide (150 ml) was added dropwise chloroacetyl chloride (8.06 g) at 5C and the mixture was stirred at ambient temperature for 20 hours. The mixture was poured into a mixture of ethyl acetate and water and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with ethyl acetate and collected by filtration to give 1- (CHLOROACETYL)-5-NITROINDOLINE (14.66 g) as a yellow crystal. 1H-NMR (DMSO-d6): 8 3. 28 (2H, t, J=8.6 Hz), 4.25 (2H, t, J=8.6 HZ), 4.64 (2H, s), 8.1-8. 2 (3H, m) ESI-MS (m/z): 263 (M+Na) +

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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. Computed Properties of C8H8N2O2

Reference Example 49 7-bromo-5-nitro-1H-indoline 5-nitro-1H-indoline (2.0 g) was dissolved in acetic acid (15.0 mL), bromine (1.0 mL) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, and this was neutralized with a 1 mol/L aqueous sodium hydroxide solution. The produced crystal was filtered and washed with water, and the resulting crystal was then dried under reduced pressure to obtain the title compound (3.3 g). 1H NMR (CDCl3) delta (ppm): 3.27(2H,t), 3.86(2H,t), 7.90(1H,s), 8.19(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 32692-19-6, its application will become more common.

Reference:
Patent; Sanwa Kagaku Kenkyusho Co., Ltd; EP2036887; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, 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. 32692-19-6 name is 5-Nitroindoline, 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.

A dry Schlenk tube was charged with Cs2C03 (266 mg, 0.816 mmol). The tube was evacuated for 30 min and then flushed with argon and 9 (150 mg, 0.272 mmol) was added to the tube, followed by Pd2(dba)3 (2.8 mg, 0.003 mmol) and X-Phos (6.5 mg, 0.014 mmol). The mixture was dissolved in dry dioxane (5 mL) and the solution was degassed in an ultrasonic bath for 20 min. Then 5-nitroindoline (67.3 mg, 0.41 mmol) was added and the mixture was stirred for 53 h at 80C. TLC (petrol ether/EtOAc 3:1 ) and mass spectroscopy indicated the formation of partially deacetylated mannoside during the progress of the reaction. Therefore, dry pyridine (2 mL) and dry acetic anhydride (1 mL) were added 50 h after the reaction started to regain fully protected mannoside. Then EtOAc (30 mL) and satd. aq. NaHC03 solution (50 mL) were added to the reaction mixture. The layers were separated and the organic phase was washed with brine (2 x 50 mL). The aqueous layers were extracted with EtOAc (3 x 30 mL). The combined organic layers were dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified with silica gel chromatography (petrol ether/EtOAc, 10:1 -1 :1 ) to give 10 (128 mg, 80%) as an orange solid.1H NMR (CDCI3): delta 2.02, 2.20 (2s, 12H, 4 OAc), 3.21 (t, J = 8.5 Hz, 2H, CH2), 4.1 1 (m, 4H, CH2, H-6a, H-5), 4.26 (dd, J = 7.3 Hz, 1 H, H-6b), 5.37 (t, J = 9.9 Hz, 1 H, H-4), 5.43 (s, 1 H, H-2), 5.53 (m, 2H, H-1 , H-3), 6.84 (d, J = 8.3 Hz, 1 H, Ar), 6.98 (m, 3H, Ar), 7.30 (t, J = 8.1 Hz, 1 H, Ar), 8.00 (s, 1 H, Ar), 8.05 (d, J = 8.8 Hz, 1 H, Ar).

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

Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; WO2012/164074; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, 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. Application In Synthesis of 5-Nitroindoline

29: 3-(5-Nitroindolin-1 -yl)phenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside (16)A dry Schlenk tube is charged with Cs2C03 (266 mg, 0.816 mmol, 3 equiv). The tube is evacuated for 30 min and then flushed with argon gas and 3-iodophenyl 2,3,4,6-tetra-O- acetyl-a-D-mannopyranoside 15 (150 mg, 0.272 mmol, 1 equiv) is added to the tube, followed by Pd2(dba)3 (2.8 mg, 0.0027 mmol, 0.01 equiv) and X-Phos (6.5 mg, 0.0136 mmol, 0.05 equiv). The mixture is dissolved in dry dioxane (5 mL). The solvent is degassed in a ultrasonic bath for 20 min. Then 5-nitroindoline (67.3 mg, 0.41 mmol, 1 .5 equiv) is added. The mixture is heated to 80C and stirred for 53 h. TLC (petroleum ether/ EtOAc 3:1 ) and mass spectroscopy helps monitoring the reaction and indicates formation of partially deacetylated mannoside during the progress of the reaction. For that reason dry pyridine (2 mL) and dry acetic anhydride (1 mL) are added 50 h after reaction start to regain fully protected mannoside. Then EtOAc (30 mL) and saturated aqueous NaHC03 solution (50 mL) are added to the reaction mixture. The layers are separated and the organic phase is washed with brine (2 x 50 mL). The aqueous layers are extracted with EtOAc (3 x 30 mL). The combined organic layers are dried with Na2S04, filtered and concentrated under reduced pressure. The residue is purified with silica gelchromatography (petroleum ether/EtOAc, gradient from 10:1 to 1 :1 ). Compound 16 (128 mg, 80%) is obtained as an orange solid.[a]D20 + 59.3 (c = 1 , CHCI3); 1H NMR (CDCI3): delta 2.02 (m, 9H, OAc), 2.20 (s, 3H, OAc), 3.21 (t, J = 8.5 Hz, 2H, CH2), 4.1 1 (m, 4H, CH2, H-6a, H-5), 4.26 (dd, J = 7.3 Hz, 1 H, H-6b), 5.37 (t, J = 9.9 Hz, 1 H, H-4), 5.43 (s, 1 H, H-2), 5.53 (m, 2H, H-1 , H-3), 6.84 (d, J = 8.3 Hz, 1 H, C6H4), 6.98 (m, 3H, C6H4, C6H3), 7.30 (t, J = 8.1 Hz, 1 H, C6H4), 8.00 (s, 1 H, C6H3), 8.05 (d, J = 8.8 Hz, 1 H, C6H3); 13C-NMR (CDCI3): delta 20.89, 20.92, 20.94, (3 OAc), 21.12 (OAc), 27.29 (CH2), 53.36 (CH2), 62.30 (C-6), 66.07 (C-4), 69.01 (C-3), 69.54, 69.56 (2C, C-2, C-5), 96.00 (C-1 ), 106.66, 107.96, 1 1 1.47, 1 14.09, 121.37, 126.13,130.70 (8C, arom. C), 143.38 (1 C, arom. C-O) 152.64, (1 C, arom. C-N), 169.92, 170.23, 170.25, 170.71 (4 C=0)

The synthetic route of 5-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; HEROLD, Janno; WO2011/73112; (2011); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 32692-19-6, These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, 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.

1) Production of N,N-dimethyl-2-(5-nitro-2,3-dihydro-1H-indol-1-yl)ethylamine: 730 mg of sodium hydride was added to an N,N-dimethylformamide solution of 1 g of 5-nitroindoline, and stirred at room temperature for 30 minutes. 1.8 g of 2-dimethylaminoethyl chloride hydrochloride was added to the reaction liquid, and stirred at 70C for 1 hour. The reaction liquid was cooled, diluted with chloroform, and washed with aqueous saturated sodium bicarbonate solution and saturated saline water in that order. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting crude product was purified through basic silica gel column chromatography (chloroform/methanol) to obtain 950 mg of the entitled compound as a yellow oil. 1H-NMR (CDCl3) delta: 8.26 (1H, dd, J=8.8, 2.4 Hz), 8.14 (1H, d, J=2.4 Hz), 6.96 (1H, d, J=8.8 Hz), 3.88 (2H, t, J=6.8 Hz), 3.64 (2H, s), 2.57 (2H, t, J=6.8 Hz), 2.30 (6H, s) ESI-MS Found: m/z [M+H] 250

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; EP2168966; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, belongs to indolines-derivatives 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 32692-19-6, Computed Properties of C8H8N2O2

General procedure: A solution of indoline (20) (1.88 mL, 16.78 mmol), tert-butyl 3-oxopyrrolidine-1-carboxylate (22) (3.73 g, 20.13 mmol) in dry methanol (20 mL) was treated with AcOH (2.37 mL, 41.95 mmol) followed by NaCNBH3 (1.26 g, 20.13 mmol) at 0 C. ;The reaction was brought to room temperature and stirred for 3 h. ;The reaction was basified with 1 N NaOH solution and product was extracted into CH2Cl2. ;The combined CH2Cl2 layer was dried (Na2SO4) and solvent was evaporated to obtain crude product. ;The crude was purified by column chromatography (EtOAc:hexanes, 1:9) to obtain the title compound

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; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem