Category: 169037-23-4

Reference of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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 indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

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:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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 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′-(m-methoxyphenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(m-methoxyphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5k): Melting point 285-287 C; white solid, 94%;1H-NMR (CDCl3, 400 MHz): delta/ppm 4.99 (d, J = 14.64 Hz, 1H), 4.68-4.71 (m, 1H), 4.39 (d, J = 10.24 Hz, 1H), 3.85 (d, J = 13.92 Hz, 1H), 3.80 (s, 3H), 3.78 (s, 3H), 3.70 (d, J = 16.92 Hz, 1H), 3.53 (d, J = 15.4 Hz, 1H), 3.03 (d, J = 11.72 Hz, 1H), 2.79-2.86 (dd, J = 13.96, 8.08 Hz, 1H), 2.72 (d, J = 13.92 Hz, 1H), 6.60-6.67 (m, 2H), 7.13-7.63 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.6, 47.3, 52.6, 53.3, 55.4, 55.5, 61.2, 67.4, 70.9, 100.8, 109.7, 114.2, 114.3, 121.5, 122.3, 122.4, 124.5, 124.6, 124.8, 126.5, 127.4, 128.6, 128.8, 128.5, 128.7, 129.4, 129.9, 130.2, 130.6, 134.6, 136.8, 138.4, 138.4, 138.7, 139.8, 139.7, 144.3, 179.4, 197.5. EI-MS: m/z 771 (M+). Anal. Calcd for C46H40F3N3O5: C, 71.58; H, 5.22; N, 5.44. Found: C, 71.66; H, 5.32; N, 5.55.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Trifluoromethoxy)indoline-2,3-dione, its application will become more common.

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

Reference of 169037-23-4, 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 169037-23-4 as follows.

General procedure: To a solution of isatin 1 (1 mmol), nitromethane/nitroethane (3 mmol) was added DABCO (5 mol %). The mixture was stirred at rt this temperature for 1-5 min. The reaction was monitered by TLC. After completion of the reaction, the mixture was extracted with ethyl acetate (3 ¡Á 5 mL). The combined organic layers were washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (ethyl acetate/hexanes: 30:70). All novel compounds were characterized by M.P., NMR, Mass and IR spectral data.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meshram; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Tetrahedron Letters; vol. 52; 44; (2011); p. 5862 – 5864;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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.

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-methoxyphenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-methoxyphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5j): Melting point 295-297 C; White solid, 92%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 5.00 (d, J = 14.64 Hz, 1H), 4.69-4.72 (m, 1H), 4.41 (d, J = 10.24 Hz, 1H), 3.87 (d, J = 13.92 Hz, 1H), 3.83 (s, 3H), 3.81 (s, 3H), 3.72 (d, J = 16.92 Hz, 1H), 3.55 (d, J = 15.4 Hz, 1H), 3.05 (d, J = 11.72 Hz, 1H), 2.84-2.90 (dd, J = 13.96, 8.08 Hz, 1H), 2.75 (d, J = 13.92 Hz, 1H), 6.62-6.68(m, 2H), 6.99-7.58 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.7, 47.4, 52.7, 53.3, 55.4, 55.5, 61.2, 67.4, 70.9, 100.9, 109.8, 114.1, 114.3, 121.3, 122.4, 124.6, 124.9, 126.5, 127.4, 128.6, 128.7, 128.6, 128.7, 129.4, 129.8, 130.2, 130.5, 131.7, 134.5, 136.8, 138.4, 138.5, 138.7, 139.8, 139.9, 140.2, 144.4, 179.3, 197.5. EI-MS: m/z 771 (M+). Anal. Calcd for C46H40F3N3O5: C, 71.58; H, 5.22; N, 5.44. Found: C, 71.69; H,5.36; N, 5.58.

Statistics shows that 5-(Trifluoromethoxy)indoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 169037-23-4.

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

These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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. category: indolines-derivatives

General procedure: The isatin ( 0.01 mol scale) was dissolved in 50 ml of CH3OH in a 150 ml round bottomed flask equipped with a reflux condenser and a stir bar. The mixture was brought to reflux that was followed by gradual addition of KBH4 (0.27 g, 0.005 mol). The reaction mixture continued to stir under reflux for 1 hour. While heating, the stopper of the round bottomed flask was removed 2-3 times and the flask was shaken to saturate the reaction mixture with air. After 1 hour, the solution was cooled to room temperature and the indirubin precipitated out of the solution. The solid was isolated by filtration and was further purified by recrystallization from 95% C2H5OH or by column chromatograph on silica gel. Indirubin and 10 indirubin derivatives in Z form were synthesized by this method. The structures of the indirubins were determined by 1H NMR, 13C NMR, MS, IR, UV and elemental analysis, and the stereochemistry was assigned by comparing the spectra data to published reports or comparing to authentic samples.

The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Cuiling; Yan, Jiaxu; Du, Mo; Burlison, Joseph A.; Li, Chi; Sun, Yanni; Zhao, Danqing; Liu, Jianli; Tetrahedron; vol. 73; 19; (2017); p. 2780 – 2785;,
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 169037-23-4 as follows. Formula: C9H4F3NO3

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., 169037-23-4

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

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:
Article; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem