Category: 19727-83-4

Synthetic Route of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-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.

6-Nitroindoline (5 g) was dissolved in 200 mL ofdichloroethane. N-Methyl-4-piperidone (5 g) was added to themixture, followed by NaHB(OAc)3 (12 g) and 1 mL of glacialAcOH. The mixture was stirred at RT overnight. A saturatedNaHC03 (200 mL) solution was added to the reaction mixtureand stirred for 1 h. The resulting mixture was separated byseparation funnel. The organic layer was extracted once withsaturated NaHC03 solution and once with brine. The resultingorganic layer was dried over MgS04, filtered andconcentrated in vacuo. The crude material was purified byflash chromatography on silica gel with 2:1 EtOAc:MeOH toafford orange oil. MS: 262 (M+l) . Calc’d. for C14H19N302 -261.3.

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

Reference:
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19727-83-4, name is 6-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 19727-83-4, Recommanded Product: 6-Nitroindoline

At room temperature, 6-nitroindoline (99 mg, 0.6 mmol) was added to the reaction tube containing p-methylthiophenol (62 mg, 0.5 mmol) and dimethyl sulfoxide (1.0 mL). After stirring uniformly at room temperature, riboflavin 1 (0.025 mmol, 8 mg) and elemental iodine (0.05 mmol, 13 mg) were added in sequence, and then vacuum oxygen protection was applied. After the reaction tube was reacted at 60C for 24 hours, it was cooled to room temperature, and saturated sodium thiosulfate solution was added to quench the reaction. Then, the reaction solution was extracted with ethyl acetate, and then washed with saturated sodium chloride solution, and the organic layers were combined and dried with anhydrous sodium sulfate, and the organic layer was concentrated by rotary evaporation.Finally, it was purified by column chromatography (n-hexane: ethyl acetate = 30: 1) to obtain a yellow solid 6-nitro-3-(4-methylphenylthio)indole 106 mg, yield 75%.

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; Zhejiang University of Technology; Jiang Xinpeng; Zhao Zongchen; Yu Chuanming; (8 pag.)CN111100056; (2020); A;,
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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Nitroindoline

Step A-Preparation of 1-(1-methyl(4-piperidyl))-6-nitroindoline 6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane, N-methyl-4-piperidone (5 g) was added to the mixture, followed by 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) was added to the reaction mixture and stirred for 1 h.The resulting mixture was separated by separation funnel, the organic layer was extracted once with saturated NaHCO3 solution and once with brine.The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford an orange oil. MS: 262 (M+1). Calc’d. for C14H19N3O2-261.32.

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2O2

l-(teri-Butylsulfinyl)-6-nitroindoline (SG4-017): To a solution of 6-nitroindoline (1.00 g, 6.09 mmol) and pyridine (1.48 mL, 18.27 mmol) in DCM (3 mL) was added a solution of t- butylsulfinyl chloride (0.751 mL, 6.09 mmol) at 0 C under Argon. The mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and washed with HC1 (1 M aq. solution, 1 x 50 mL), water (1 x 50 mL), and brine (1 x 50 mL). The organic layer was dried ( a2S04) and concentrated under reduced pressure. The resulting residue was triturated using EtOAc/hexanes to provide the title compound as a dark yellow solid (1.252 g, 77%). Mp: 108 C (dec). NMR (400 MHz, CDCh) delta: 7.82 (dd, J= 8.1, 2.1 Hz, 1H), 7.67 (d, J= 2.1 Hz, 1H), 7.25 (d, J= 8.1 Hz, 1H), 4.36 (td, J= 10.5, 6.8 Hz, 1H), 3.60 (td, J = 10.5, 6.8 Hz, 1H), 3.30 (dddd, J= 17.3, 10.5, 6.8, 0.8 Hz, 1H), 3.17 (dddd, J= 17.3, 10.5, 6.8, 0.8 Hz, 1H), 1.34 (s, 9H). HPLC-MS (ESI+): m/z 559.3 [70%, (2M+Na)+], 291.2 [100%, (M+H)+].

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas, J.; LAWRENCE, Harshani, R.; (257 pag.)WO2016/22460; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 19727-83-4, name is 6-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. Recommanded Product: 19727-83-4

Step A 1-Methyl-6-nitroindoline Potassium bis(trimethylsilyl)amide (67 ml of a 0.5M toluene solution) was added slowly to a stirred solution of 6-nitroindoline (5.0 g) in anhydrous tetrahydrofuran (200 ml) at -78 C. under a nitrogen atmosphere. Iodomethane (2.09 ml) was added then the reaction mixture was allowed to warm to room temperature then stirred overnight. Methanol (5 ml) was added then the solution was evaporated to dryness. The residue was dissolved in diethyl ether (300 ml), washed with water, saturated brine then dried (magnesium sulphate) and evaporated to dryness. The crude product was purified by column chromatography on silica using 10% ethyl acetate/petroleum ether (60-80)?30% ethyl acetate/petroleum ether (60-80) and the product crystallized from diethyl ether/petroleum ether (60-80) to afford 0.9 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Merck, Sharp & Dohme, Ltd.; US5696110; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19727-83-4, 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. 19727-83-4 name is 6-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.

General procedure: Into a Schlenk tube (volume: ca. 20 mL) connected to a balloon partially filled with Ar gas, Pd/LDH (75 mg, Pd: 3 mol %), 4-isopropylpiperidine (0.5 mmol), decane (internal standard, 0.1 mmol), octane (2.0 mL), and a Teflon-coated magnetic stir bar were successively placed, and the reaction mixture was vigorously stirred at 120 C, in 1 atm of Ar. After the reaction was completed, the conversion of 4-isopropylpiperidine and the yield of 4-isopropylpyridine were determined by GC analysis. The reactions of piperidine and 4-methylpiperidine were conducted in a test tube with an Ar balloon. During these reactions, the upper side of the test tube was cooled by refrigerant (-5 C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Article; Oyama, Takashi; Yatabe, Takafumi; Jin, Xiongjie; Mizuno, Noritaka; Yamaguchi, Kazuya; Chemistry Letters; vol. 48; 6; (2019); p. 517 – 520;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 19727-83-4, name is 6-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. Recommanded Product: 19727-83-4

5-Trifluoromethyl-7-pyridono[5,6-e]indoline (Compound 419, structure 49A of Scheme XLV, where R1 =trifluoromethyl, R2 =H) 6-Aminoindoline A solution of 6-nitroindoline (1 g, 6.1 mmol) in 50 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (100 mg) at rt for 3 h. Filtration over celite afforded 1.0 g (98%) of 6-aminoindoline. Data for 6-aminoindoline: 1 H NMR (400 MHz, CDCl3) 7.40 (d, J=7.4, 1H), 6.05 (d, J=2.0, 1H), 6.03 (d, J=7.5, 1H), 3.67 (bs, 1H), 3.49 (t, J=8.1, 2H), 3.48 (bs, 2H), 2.90 (t, J=8.2, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-nitroindoline (5.00 g, 30.5 mmol) in CH2C12 (100 mL) was added Et3N (4.25 mL, 3.08 g, 30.5 mmol) and TFAA (4.23 mL, 6.40 g, 30.5 mmol) and the resulting solution stirred at RT for Ih. More Et3N (4.25 mL, 3.08 g, 30.5 mmol) and TFAA (4.23 mL, 6.40 g, 30.5 mmol) were added and the solution was stirred at RT for another 2h. Water (100 mL) was added and the mixture was extracted with CH2C12 (3×100 mL), dried (MgSO4), and concentrated to yield 2,2,2-trifluoro-1-(6-nitroindolin-1- yl)ethanone (8.9 g, crude yield > 100%) as a yellow-brown solid.

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, 6-Nitroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; WO2006/71940; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 19727-83-4, 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. 19727-83-4 name is 6-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.

1-(6-Nitroindolin-1-yl)-acetonitrile A stirred mixture of 6-nitroindoline (2.0 g, 12 mmol), potassium carbonate (3.36 g, 24 mmol), sodium iodide (3.65 g, 24.4 mmol), acetone (20 mL) and chloroacetonitrile (1.5 mL, 24 mmol) was heated under reflux for 16 h. The mixture was cooled to room temperature, filtered and the filter-cake washed with ethyl acetate. The filtrate was concentrated in vacuo and purified by column chromatography [SiO2; heptane-ethyl acetate (9:1)] to give the product (1.3 g, 53% yield) as a pale yellow solid: IR numax (Nujol)/cm-1 1615, 1513, 1487, 1343, 1293, 1145, 804 and 739; NMR deltaH (400 MHz, CDCl3) 3.11 (2H, t, J 7.5 Hz), 3.59 (2H, t, J 7.5 Hz), 4.14 (2H, s), 7.19-7.23 (1H, m), 7.31-7.33 (1H, m) and 7.69-7.72 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Patent; Vernalis Research Limited; US6380238; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 19727-83-4 as follows. Application In Synthesis of 6-Nitroindoline

Reference Example 58 In 50 ml of methylene chloride was dissolved 2.5 g of 6-nitroindoline, and then 6.37 ml of triethylamine was added thereto. Under ice cooling, 3.51 g of methanesulfonyl chloride was added dropwise, the reaction solution was stirred at room temperature for 3 hours, and then ice-water was added thereto, followed by 1 hour of stirring. The reaction solvent was removed by evaporation under reduced pressure, a 1M aqueous hydrochloric acid solution was added to the residue, and precipitated was filtrated off, whereby 3.52 g of 1-methylsulfonyl-6-nitroindoline was obtained as a brown solid.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; EP1632477; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem