Month: June 2021

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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C14H13NO3

The title compound from Preparative Example 23 Step A (1.54 g, 8.23 mmol) was dissolved in ethanol (50 mL) and the title compound from Step C above (2 g, 8.23 mmol) was added. The mixture was stirred at room temperature for 1 h to become a suspension. The solvent was removed to afford the title compound as an off-white solid (3.3 g, quant.).1H-NMR (400 MHz, DMSO-d6): delta=2.00-2.18 (m, 3H), 2.27-2.43 (m, 2H), 2.50-2.63 (m, 2H), 3.30-3.38 (m, 1H), 4.46 (tt, 1H), 7.00 (d, 1H), 7.18 (d, 1H), 7.62 (t, 1H), 7.93-8.00 (m, 4H), 10.1 (s, 1H)

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; AC Immune, S.A.; US2011/280808; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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.

General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methoxyindolin-2-one, its application will become more common.

Reference:
Article; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 446292-08-6, A common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, molecular formula is C22H19N3O6, 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.

210.7 g (0.5 mol) of (S)-2-{[2-oxo-3-(4-(3-oxomorpholine)benzene] prepared in Example 7 was added to the reaction flask.Based on oxazolidine-5-yl]methyl}isoindole-1,3-dione (formula VII), 1500 ml of anhydrous ethanol,500 ml of a 30% aqueous solution of methylamine was stirred and heated to 40C to 60C for 8 hours.TLC control (dichloromethane:methanol = 20:1, volume ratio) reaction is complete, with 10% hydrochloric acid to adjust the pH to between 1-2, precipitated a lot of white solids, cooled to about 15 C, stirred for 2 hours, filtered The filter cake was washed with 300 ml of anhydrous ethanol and dried under reduced pressure to obtain 147.0 g of a white solid (compound of formula VIII) with a molar yield of 89.7% and an HPLC purity of 98.7%.

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Peking University Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Xu Hong; Fan Yang; Zhang Zheng; Wang Wei; Ren Juan; (14 pag.)CN105085431; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, 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-Chloro-7-methylindoline-2,3-dione

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

The synthetic route of 5-Chloro-7-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(o-bromophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-bromophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5b): Melting point 247-249 C; white solid, 96%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.82 (d, J = 13.96 Hz, 1H), 4.58-4.61 (m, 1H), 4.49 (d, J = 10.24 Hz, 1H), 3.79 (d, J = 13.2 Hz, 1H), 3.60 (d, J = 16.82 Hz, 1H), 3.39 (d, J = 5.4 Hz, 1H), 2.94 (d, J = 13.96 Hz, 1H), 2.71-2.77 (m, 1H), 2.41 (d, J = 13.92 Hz, 1H), 6.56-6.61 (m, 2H), 6.98-7.65 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 40.6, 47.4, 52.7, 53.2, 61.3, 67.2, 70.9, 100.8, 110.1, 121.9, 122.4, 122.5, 123.8, 124.5, 126.4, 126.5, 127.2, 128.3, 128.4, 128.5, 128.6, 128.7, 128.9, 129.1, 131.4, 131.6, 131.8, 133.2, 136.3, 138.2, 138.5, 138.6, 144.6, 179.5, 197.1. EI-MS: m/z 869 (M+). Anal. Calcd for C44H34Br2F3N3O3: C, 60.77; H, 3.94; N, 4.83; Found: C, 60.85; H, 3.83; N, 4.72.

The chemical industry reduces the impact on the environment during synthesis 5-(Trifluoromethoxy)indoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6341-92-0, name is 6-Chloroisatin, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: indolines-derivatives

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, mp 196-198 C.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4721712; (1988); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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.

General procedure: A mixture of 2-(7-methoxynaphthalen-1-yl)ethanamine (compound 3, 101 mg, 0.5 mmol), sodium acetate (82 mg, 1.0 mmol) and cyclic anhydrides 1.0 mmol) in 5mL acetic acid was heated to reflux for 3 h in a round bottomed flask. After the completion of reaction (as evidenced by TLC), the resulting mixture was concentrated under reduced pressure and washed with ethyl acetate (10 mL×3), then the concentrated organic layer was purified by column chromatography on silica gel to obtain pure product.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Ying; Pi, Weiyi; Ang, Wei; Liu, Yuanyuan; Li, Chunlong; Zheng, Jiajia; Xiong, Li; Yang, Tao; Luo, Youfu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1672 – 1676;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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.

To a stirred solution of 7-fluoroindoline-2,3-dione (500 mg, 3.03 mmol) in DMF (5 mL) were successively added K2C03 (502 mg, 3.63 mmol) and methyl iodide (0.199 mL, 3.18 mmol). The resulting mixture was stirred at RT for 1 hr. The mixture was quenched with water, diluted with EtOAc and saturated aqueous NaHC03 solution and both phases were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgS04, filtered and concentrated under reduced pressure to afford the title product (497 mg, 2.219 mmol, 73.3% yield) as yellow solid. Rt = 0.69 min (UPLC-MS); ESI-MS = 179.9 [M+1]+ (UPLC-MS).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroisatin, its application will become more common.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, 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 667463-64-1, SDS of cas: 667463-64-1

General procedure: Unless indicated otherwise, a solution of 2-aminobenzamide 1 (0.1 mmol), isatin 2 (0.1 mmol), the catalyst 4e (0.02 mmol), and 5 A molecular sieves (30 mg) in 1,2-dichloroethane (2 mL) was stirred at 70 C for 12 h. Next, the reaction mixture was diluted with acetone, which was then filtered to remove molecular sieves and the solid powder was washed with acetone. The resultant solution was condensed by evaporation under reduced pressure, which was further purified through preparative thin layer chromatography on silica gel to yield pure products 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Yan; Liu, Yan; Tu, Shu-Jiang; Shi, Feng; Tetrahedron Asymmetry; vol. 24; 20; (2013); p. 1286 – 1296;,
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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

General procedure: Procedure M2. A mixture of the appropriate 2-(bromoalkyl)-isoindoline-1,3-dione (1 equiv)with 1,2,3,4-tetrahydoisoquinoline (1 equiv) in the presence of K2CO3 (2.5-3 equiv) was stirred inacetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under vacuum, producinga residue which was further dissolved in 40 mL of sodium bicarbonate and extracted with ethyl acetate(3 x 30 mL). The organic layer was acidified 2 M HCl and extracted with distilled water (3 x 30 mL).Then, the combined aqueous extracts were alkalized using 4M NaOH, extracted with DCM and driedwith anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gelcolumn chromatography (S4) yielding a yellow oil. The final product was obtained in the form ofhydrochloride salt. The following compounds were obtained.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem