Month: June 2021

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. 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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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;,
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., 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;,
Indoline – Wikipedia,
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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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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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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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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., name: 5-Nitroindoline

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

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

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
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Adding a certain compound to certain chemical reactions, such as: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 1074-82-4, Product Details of 1074-82-4

Synthesis of the protected ketone monomer was conducted based on a modification of a previously reported protocol (50). Chloroacetone (10 mE, 12.5 mmol) and the potassium salt ofphthalimide (25.5 g, 13.8 mmol) were added to 150 mE of stirred dry acetone. The solution was then heated to 80 C. for 20 hours, after which it was cooled to room temperature and the acetone was removed in a rotary evaporator. The resulting solid was then redissolved in methylene chloride and washed repeatedly with water. The methylene chloride layer was dried over magnesium sulfate, filtered, and removed using a rotary evaporatot The resulting yellow crude solid was washed with diethyl ether several times until the solid became white; this solid was subsequently dried in a vacuum oven to yield purified intermediate A (Scheme 1A). Intermediate A (lOg, 50 mmol) was then added to 180 mE of toluene along with ethylene glycol (5.85 mE, 100 mmol) and dry para-tolenesulfonic acid (934 mg, 5 mmol) and refluxed for 15 hours. The reaction mixture was cooled to room temperature and the ethylene glycol layer was extracted three times with diethyl ether. The toluene and ether fractions were combined and washed three times with 5% (w/v) NaOH followed by deionized water. The organic layer was dried over magnesium sulfate and solvent was removed in a rotary evaporatot The crude was recrystallized from ethanol to yield pure intermediate B (Scheme 1B). Intermediate B was subsequently added to 100 mE of deionized water along with 15 g of NaOH and refluxed for 2 days, with an additional 60 g of NaOH added slowly over the course ofthe reflux. Afierwards, the reaction mixture was cooled to room temperature and extracted three times with 50 mE dichloromethane. The organic layers were then combined and dried over magnesium sulfate, filtered, and concentrated in a rotary evaporator to yield pure product C (Scheme 1C), a slightly yellow oil. Finally, the monomer was prepared by adding product C (21.1 mE, 180 mmol) to a 20% (w/v) NaOH solution (in water) containing 4-hydroxy TEMPO (10 mg, 0.06 mmol). This reaction mixture was brought to 0 C. in an ice bath and methacryloyl chloride (16.5 mE, 174 mmol) was added drop- wise over 2 hours under nitrogen flow. The ice bath was then allowed to warm to room temperature and the reaction left to stir overnight in darkness. Afier this time, stirring was halted and the product was allowed to collect at the top of the reaction flask. The pure monomer product (along with inhibitor) (shown in Scheme 1 D) was then isolated using a separatory funnel. The monomer was stored in the darkness at -20 C. until use. 1H NMR (600 MHz) in DMSO-d5: RNHCH2C(OCH2CH2O)CH3, 1.3 ppm, singlet, 3H;CH2CCH3CONHR?, 2 ppm, singlet, 3H; RNHCH2C(OCH2CH2O)CH3, 3.5 ppm, doublet, 2H; RNHCH2C(OCH2CH2O)CH3, 4 ppm, singlet, 4H; CH2CCH3CONHR?,5.35-5.65 ppm, doublet, 2H; CH2CCH3CONHR?, 6 ppm, sin-glet, 1H.

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; McMaster University; Hoare, Todd; Bakaic, Emilia; Smeets, Niels M.B.; Deng, Xudong; (55 pag.)US2016/151535; (2016); A1;,
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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. 337536-15-9, name is 4-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromoisoindolin-1-one

Step 1. A mixture of 2,4-dichloropyrimidine (116 mg, 0.78 mmol), 4-bromoisoindolin-l-one (150 mg, 0.71 mmol), K2CO3 (196 mg, 1.41 mmol) in DMF (3 mL) was degassed and purged with N2 three times, and then the mixture was stirred at 80C for 14 hours under an inert atmosphere. The resulting mixture was filtered and concentrated under reduced pressure. Purification by prep-TLC (Si02, petroleum ether/ethyl acetate = 3 : 1) provided 9 (80 mg) as a light yellow solid which was used directly in the next step without further purification.

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NUMERATE, INC.; RAIMUNDO, Brian; KOLTUN, Elena S.; GRIFFIN, John; STANGELAND, Eric; (93 pag.)WO2018/49324; (2018); A1;,
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