Category: 32692-19-6

Reference of 32692-19-6, A common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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) Preparation of 1-(2-chloroacetyl)-5-nitroindoline5-nitroindoline (16.4g, 100mmol) was dissolved in ethyl acetate (200ml), and then chloroacetyl chloride (9.6ml 120mmol) was slowly added at 40 C. The resulting mixture was heated to 80 C, and reacted for 0.5 hour. The reaction mixture was cooled and filtered by suction. The filtrate was crystallized to produce 1-(2-chloroacetyl)-5-nitroindoline (22g) as a grey solid in a yield of 92%.

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

Reference:
Patent; KBP Biosciences Co., Ltd.; LO, Hoyin; WANG, Aichen; ZHANG, Qian; EP2930167; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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.

Bromine (1.569 mL, 30.5 mmol) was added dropwise to an ice-cold solution of 5-nitro indoline (5 g, 30.5 mmol) in acetic acid (50 mL), and the mixture was stirred for 1 h. Acetic acid was concentrated under reduced pressure, and the resulting solid was triturated with water to afford the title compound (6 g, 80%) as a yellow solid, which was carried on to the next step without further purification. lU NMR (300 MHz, DMSO-i/6): delta 8.07 (d, J= 2.1 Hz, lH), 7.84 (d, J = 2.1 Hz, 1H), 7.3 (bs, 1H), 3.7 (t, J= 8.7 Hz, 2H), 3.17 (t, J= 8.4 Hz, 2H). ESI-MS m/z = 243 (M+H)+.

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:
Patent; GLAXOSMITHKLINE LLC; CHEUNG, Mui; TANGIRALA, Raghuram, S.; WO2014/81994; (2014); 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, Safety of 5-Nitroindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

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; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 32692-19-6, A common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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 solution of 5-nitroindoline (6) (0.5 g, 3.05 mmol) in DMF (10 mL) was treated with NaH (0.39 g, 9.75 mmol, 60% wt in mineral oil) at 0 C resulting in an orange mixture. ;The reaction mixture was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (0.87 g, 6.09 mmol) resulting in a dark red mixture. ;The reaction was heated to 90 C and stirred for 1.5 h. ;After allowing the reaction to cool to room temperature, water was added and the product was extracted into EtOAc. ;The combined ethyl acetate layer was washed with water, brine and dried (Na2SO4). ;Solvent was evaporated and the crude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain the title compound (0.4 g, 56%) as a solid. 1H NMR (DMSO-d6) delta 7.96 (dd, 1H, J = 2.1, 8.7 Hz), 7.79 (d, 1H, J = 2.1 Hz), 6.49 (d, 1H, J = 9.0 Hz), 3.72 (t, 2H, J = 8.7 Hz), 3.39 (t, 2H, J = 6.6 Hz), 3.04 (t, 2H, J = 8.7 Hz), 2.44 (t, 2H, J = 6.3 Hz), 2.18 (s, 6H).

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

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

Electric Literature of 32692-19-6, 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.

[0590] Procedure: To a stirred solution of 4-chloro-7-methoxyquinoline (0.05 g, 0.25 mmol) in 1,4- dioxane (5 mL) were added 5-nitroindoline (0.046 g, 0.28 mmol), cesium carbonate (0.25 g, 0.77mmol) and Xanthphos (0.029 g, 0.051 mmol). The resulting mixture was purged with argon for 15 min and added Pd2(dba)3 (0.023 g, 0.025 mmol) was added and the mixture was purged for another 10 min. Resulting mixture was stirred for 16h at 100 C. Progress of the reaction was monitored by TLC. Reaction mixture was filtered through celite bed and filtrate was diluted with ethyl acetate (20mL), washed with water (2 x 10mL) followed by brine (10 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude was purified by combiflash using 55-60% ethyl acetate in hexane to afford 7-methoxy-4-(5-nitroindolin-1-yl)quinoline as yellow solid (0.12 g, 75%).1HNMR (400 MHz, DMSO-d6): delta 8.83 (d, J = 4.4 Hz, 1H), 8.08 (s, 1H), 7.91-(d, J = 8.8 Hz, 1H), 7.73 (d, J = 9.2 Hz, 1 H), 7.46 (s, 1H), 7.36 (d, J = 4.8 Hz, 1H), 7.23 (d, J = 9.2 Hz, 1H), 6.24 (d, J = 8.8 Hz, 1H), 4.26 (t, J = 8.4 Hz, 2H), 3.93 (s, 3H), 3.32 (t, J = 8.4 Hz, 2H); LCMS (ES) m/z = 322.1 [M+H]+.

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

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); 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, Recommanded Product: 32692-19-6

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.

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:
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., COA of Formula: C8H8N2O2

REFERENCE EXAMPLE 6; 5-Amino-1-isopropy.sulfonylindofine; a) 1-isopropy.sulfonyf~5-?itroindoline; 1 mL of TEA (7.61 mmol) and isopropylsulfonyl chloride (0.5 mL, 4.57 mmoi) were added at 0 0C to a solution of 5-nitroindoline (0.5 g, 3.05 mmol) in CH 2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 48 h and then at reflux temperature for 18 h. The crude product obtained was diluted with a saturated aqueous solution of NaHCOs and extracted thrice with CH2Cl2. The combined organic phases were separated, dried over Na2SO4 and the solvent was evaporated to dryness. The desired compound was obtained in quantitative yield and used in next step without further purification.

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

Reference:
Patent; PALAU PHARMA, S.A.; SALAS SOLANA, Jorge; ALMANSA ROSALES, Carmen; SOLIVA SOLIVA, Robert; FONTES USTRELL, Montserrat; COMELLES ESPUGA, Josep; WO2010/34740; (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, Recommanded Product: 5-Nitroindoline

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.

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; 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

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. Safety of 5-Nitroindoline

Manufacturing Example 1 tert-Butyl 5-nitro-1-indolinecarboxylate To a solution of 500mg (3.05mmol) of 5-nitroindoline in 10mL of anhydrous dichloromethane was added 798mg (3.65mmol) of di-tert-butyl dicarbonate under ice cooling, and the mixture was stirred for 1.5 hours. Then, to this mixture was added catalytic amount of 4-dimethylamiopyridine and the mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was washed with saturated saline solution and dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 6/1) to give 800mg (99%) of the title compound.

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

Reference:
Patent; Daiichi Asubio Pharma Co., Ltd.; EP1775298; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, 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.

A solution of 5-nitro-2,3-dihydro-lH-mdole (1.0 g, 6.1 mM) in DMF is treated with CsCO3 (3.0 g, 9.1 mM) and 2-Chloro-N,N-diethyl-acetamide (1.1 g, 7.3 mM) and heated to 8O0C for 16 hours. The solution Is cooled, poured into water, extracted with EtOAc, the organic layer separated, dried (MgSO4) and the solvent removed at reduced pressure. The residue is recrystallized from EtOH. This solid is suspended in EtOH, treated with 10% Pd/C (0.2 g) and the reaction hydrogenated on a Parr Shaker at 50 psi for 2 hours. The reaction is then filtered and the solvent removed at reduced pressure to give the product as a gray solid (0.8 g, 13%). LC/MS 0.46 min. 249 (M+H, 100%); IH-NMR (300 MHz, DMSO-d6) delta 6.56 (m, IH), 6.51 (m, IH), 6.45 (s, IH), 3.80 (bs, 2H)5 3.62 (s, 2H), 3.30 (m, 2H), 3.26 (m, 4H), 2.91 (m, 2H), 1.21 (s, 3H), 1.20 (s, 3H).

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

Reference:
Patent; ASTRAZENECA AB; WO2007/97697; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem