Category: indolines-derivatives

Electric Literature of 65826-95-1, These common heterocyclic compound, 65826-95-1, name is 5-Methylindoline, 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.

5-Methylindoline (1.0 g, 7.5 mmol) was stirred in 3N HC1 (20 mL) at 0 C. Sodium nitrite (0.621 g, 9.0 mmol) in water (2 mL) was added dropwise and the mixture was stirred at 0 C for 5 min. followed by RT for 20 min. The reaction mixture was extracted with DCM (500 mL), and the organic layer was dried over sodium sulfate and concentrated under vacuum to obtain 1.2 g of 5-methyl-l-nitrosoindoline.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; CHAKRAVARTY, Sarvajit; HART, Barry, Patrick; JAIN, Rajendra, Parasmal; WO2011/103460; (2011); A1;,
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Electric Literature 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: 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,p-dichlorophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o,p-dichlorophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5e): Melting point 288-290 C White solid, 94%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.86 (d, J = 14.00 Hz, 1H), 4.68 (d, J = 13.92 Hz, 1H), 4.49-4.53 (m, 1H), 3.85 (d, J = 13.2 Hz, 1H), 3.58 (d, J = 16.82 Hz, 1H), 3.26 (d, J = 15.4 Hz, 1H), 2.95 (d, J = 13.96 Hz, 1H), 2.77-2.85 (m, 1H), 2.38 (d, J = 13.92 Hz, 1H), 6.49-6.59 (m, 2H), 6.00-7.76 (m, 19H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 40.6, 46.3, 51.9, 52.3, 63.3, 65.5, 70.4, 99.3, 110.5, 121.8, 122.4, 123.9, 124.2, 126.4, 126.6, 126.5, 127.1, 128.4, 128.5, 128.6, 129.0, 129.2, 130.6, 132.4, 133.5, 134.2, 135.6, 135.8, 135.9, 136.8, 137.4, 138.1, 138.5, 132.9, 144.5, 177.8, 199.7. EI-MS: m/z 849 (M+). Anal. Calcd for C44H32Cl4F3N3O3: C, 62.21; H, 3.80; N, 4.95; Found: C, 62.36; H, 3.99; N, 4.83.

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; 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);,
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Reference of 111992-61-1, 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 111992-61-1 as follows.

EXAMPLE 145 Synthesis of 4-(2,2-dimethyl-3-phthalimidopropylthio)pyridine To a solution of 0.56 g (5.0 mmol) of 4-mercaptopyridine and 1.48 g (5.0 mmol) of (N-3-bromo-2,2-dimethylpropyl)phthalimide in 20 ml of dimethylformamide, 0.75 ml (5.0 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80 C. for 8 hours. Water was added, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to give 12.0 g of the desired compound (71.6% yield, colorless columns). NMR (200 MHz, CDCl3) delta: 1.13 (6H, s), 3.03 (2H, s), 3.70 (2H, s), 7.17 (2H, dd, J=1.6, 4.6 Hz), 7.72-7.92 (4H, m), 8.38 (2H, dd, J=1.6, 4.6 Hz). IR (KBr) cm-1: 3030, 2960, 1715, 1580, 800, 720.

According to the analysis of related databases, 111992-61-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US5246948; (1993); A;,
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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., Recommanded Product: 169037-23-4

Example 29 3-Cyclopentyl-2-(2,3-dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-N-pyrazin-2-yl-propionamide A stirred suspension of sodium hydride (60% dispersion in oil, 208 mg) in N,N-dimethylformamide (20 mL) at 0 C. was treated with a solution of 5-trifluoromethoxy-1H-indole-2,3-dione (1.0 g) in N,N-dimethylformamide. The reaction mixture was stirred for 30 min at 0 C. and then 2-bromo-3-cyclopentyl-propionic acid methyl ester (prepared as in Example 1, 1.22 g) was added and it was stirred for 1 h at 0 C. It was then slowly allowed to warm to room temperature and stirred for another 3 h at room temperature. After this time, the reaction mixture was diluted with water and extracted with methylene chloride. The organic layers were combined and dried over sodium sulfate, filtered and the filterate concentrated in vacuo. The crude material was purified by column chromatography (silica gel) to afford 3-cyclopentyl-2-(2,3-dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-propionic acid methyl ester (1.0 g, 60%).

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; Kester, Robert Francis; US2012/142705; (2012); A1;,
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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., Recommanded Product: 169037-23-4

Step 1. Preparation of 2-amino-5-(trifluoromethoxy)benzoic Acid 5-(Trifluoromethoxy)isatin (15.0 g, 65 mmol) and potassium hydroxide pellets (4 g) were mixed in water (35 mL) and cooled to 0 C. With vigorous stirring, a solution of 30% aqueous hydrogen peroxide (11.7 g), potassium hydroxide pellets (5.8 g), and water (80 mL) was added drop-wise keeping the temperature below 10 C. After stirring 1 hour at 0 C., glacial acetic acid (22 mL) was added dropwise, causing foaming and formation of a precipitate. The contents were stirred overnight and filtered to afford the 2-amino-5-trifluoromethoxybenzoic acid as an amber solid (12.5 g, 87%). A small amount was recrystallized from ethyl acetate-hexanes to afford amber needles for an analytical sample and the remaining compound was used without further purification: mp 142.5-144.2 C. 1 H NMR (CDCl3, 300 MHz) 7.98 (s, 1H), 7.18 (d, 1H, J=8.0 Hz) 6.62 (d, 1H, J=8.0 Hz), 6.40 (brs, 2H). Anal. Calc’d for C8 H6 NO3 F3: C, 43.45; H, 2.73; N, 6.33. Found: C, 43.40; H, 2.65; N, 6.35.

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:
Patent; G.D. Searle & Co.; US6077850; (2000); A;,
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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. 6341-92-0, name is 6-Chloroisatin, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4ClNO2

In 25 ml sealed tube by adding 1 a (0.5 mmol, 88.6 mg), 2 h (0.5 mmol, 90.8 mg), iodine simple substance (0.25 mmol, 63.5 mg), triethylamine (0.25 mmol, 25.3 mg) and chlorobenzene (2 ml), then put into 130 C in oil bath stirring reaction 10 h. Add 50 ml water quenching reaction, extracted with ethyl acetate (50 ml × 3), the organic phase after the mass concentration is 10% of Na2 S2 O3 Solution and saturated salt water are successively washing, drying with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=5/1) to obtain the target product 3 t (115.9 mg, 82%). The compound of the characterization data are as follows

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; Xinxiang Medical University; Gao Qinghe; Liu Xingxia; Liu Zhaomin; Yang Limin; Yuan Huan; He Shuang; (16 pag.)CN107501180; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, Application In Synthesis of N-(5-Bromopentyl)phthalimide

General procedure: To a suspension of compound 9-12 and potassium carbonate in ACN, was added dropwise N-methylbenzylamine or piperidine under stirring and the reaction mixture was refluxed for 24 h. The reaction mixture was cooled and filtered. After evaporation of the filtrate, purification by column chromatography on silica gel (cyclohexane/EtOAc/TEA) yielded compounds 16 and 17.

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, N-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ghedira, Donia; Voissiere, Aurelien; Peyrode, Caroline; Kraiem, Jamil; Gerard, Yvain; Maubert, Elise; Vivier, Magali; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; Farhat, Farhat; Weber, Valerie; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 51 – 67;,
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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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., name: 5-Nitroindolin-2-one

To a suspension of the lactam (10.0 g, 56 mmol) in 200 ml of 1 ,2-dichloroethane, was added POBr3 (15.3g, 53.2 mmol) at RT. The resulting mixture was heated at reflux temperature in a 9OC oil bath for 0.5 hour (the reaction formed a copious amount of precipitate, and an oil bath was preferred over a heating mantle, as it provided gentle heating and avoided a darkening of the precipitate). The reaction was cooled just below reflux temperature, and imidazole (4.57 g, 62 mmol) was added in one portion. The resulting gummy suspension was heated at reflux temperature in an oil bath for another 2 hours. The reaction was cooled to RT, and 100 mL of ice-water was added. Solid NaHCO3 (ca. 50 g) was added to the mixture until no further gas was evolved. The suspension was extracted with DCM (4chi), and the combined DCM extracts were washed with 300 mL of brine. The DCM extracts were filtered through silica gel and concentrated to dryness to afford a crude product. The crude product was recrystallized from chloroform to give 5.41 g of the desired compound as a white solid. The filtrate was concentrated to dryness, and the residue was purified by flash column chromatography (30% EtO Ac/Hex) to give an additional 2.6 g of desired product. MS (ESI) m/e (MH-H+): 242.

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; COBURN, Craig, A.; MCCAULEY, John, A.; LUDMERER, Steven, W.; LIU, Kun; VACCA, Joseph, P.; WU, Hao; HU, Bin; SOLL, Richard; SUN, Fei; WANG, Xinghai; YAN, Man; ZHANG, Chengren; ZHENG, Mingwei; ZHONG, Bin; ZHU, Jian; WO2010/111483; (2010); A1;,
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Related Products of 40314-06-5, A common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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.

he starting materials were 5-methyl-phthalimide (300 mg, 1.86 mmol) and K2CO3 (257.39 mg, 1.86 mmol), in 2 mL of DMF. 6-bromoethyl hexanoate (0.33 mL, 1.86 mmol) was added to this solution, and the reaction mixture was heated at 120ºC for 24 hours. After the reaction time elapsed, it is diluted with water and an extraction with ethyl acetate (3x5mL) was performed, the organic phase was dried on MgSO4, filtered and concentrated in the rotary evaporator. A yellow liquid was obtained (564 mg, quantitative yield). 1H-NMR (C3D6O): delta 7.70 (d, 1 H, Harom, J = 7.8 Hz); 7.61 (d, 2H, Harom, J = 8.4 Hz); 4.03 (c, 2H, O-CH2CH3, J = 7.1 Hz); 3.61 (t, 2H, N-CH2, J = 7.1 Hz); 2.50 (s, 3H, Ar-CH3); 2.26 (t, 2H, CH2-CO, J = 7.4 Hz); 1.70 – 1.57 (m, 4H, CH2); 1.40 – 1.32 (m, 2H, CH2); 1.16 (t, 3H, O-CH2CH3, J = 7.2 Hz). 13C-NMR (C3D6O): 172.7 (COOEt); 168.1 (CO); 168.0 (CO); 145.4 (Carom); 134.5 (CHarom); 132.8 (Carom); 129.8 (Carom); 123.4 (CHarom); 122.8 (CHarom); 59.6 (O-CH2CH3); 37.4 (N-CH2); 33.6 (CH2-CO); 28.1 (CH2); 26.1 (CH2); 24.4 (CH2); 21.0 (Ar-CH3); 13.7 (O-CH2CH3). HR LSIMS: Calculated for C17H21NO4Na (M+Na)+ 326.1368; found 326.1371 (deviation -0.9 ppm).

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; Universidad De Granada; EP2045239; (2009); A1;,
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Synthetic Route of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: GN/SO3H (80 mg) was added to the 3 mL of EtOH/water (1:1) and dispersed for 30 min. Then, malononitrile (1 mmol), isatin (1 mmol), and dimedone (1 mmol) were added to the mixture and the mixture was heated to reflux and kept at this temperature for an appropriate time. After the time of reaction was completed, water was separated by centrifuging followed by extracting the crude product by ethyl acetate. The solvent was dried using Na2SO4 and removed from the reaction by evaporation with a rotary evaporator. Finally, the crude product was recrystallized in hot ethanol to achieve the pure product. The GN/SO3H nanocomposite was washed and reused several times.

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

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6979 – 6993;,
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