Category: indolines-derivatives

Application of 102359-00-2,Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

Example 12 To a solution of 0.88g of 5-carboxyoxindol in 10 ml of DMF was added under ice-cooling 0.82 ml of triethylamine, and 0.77 ml of isobutyl chloroformate was added thereto subsequently. The mixture was stirred at the same temperature for 1 hour. Then, 1.1g of 1-benzylpiperazine was added thereto, and the mixture was stirred at room temperature overnight. After the reaction was completed, DMF was removed under reduced pressure, and to the residue was added an aqueous sodium hydrogencarbonate solution and extracted with chloroform. After washing with water and drying over magnesium sulfate, chloroform was distilled off under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent: methylene chloride: methanol = 50:1) and recrystallized from isopropyl alcohol to give 0.7g of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol. (Not claimed) m.p.: 151-153C

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

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; EP168003; (1991); B1;,
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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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H4N2O4

Example 1 Preparation of 6-nitrophthalamic acid (2) Commercially available 4-nitro-isoindole-1,3-dione (1) (25 g, 0.13 mol) was stirred in water (300 mL) at 0 C. Over a few minutes, an aqueous solution of sodium hydroxide (30% w/w, 35 g, 0.26 mol) was added. The mixture was stirred for 1.5 h at 0-5 C. The cold solution was acidified with concentrated HCl (22 mL, 0.26 mol) and the product precipitated as a white solid. After allowing to stand overnight in a refrigerator, the mixture was filtered to afford the title compound (26.3 g, 96%) as a white solid: 1H NMR (300 MHz, DMSO) delta 8.2 (s, 1H), 8.15 (d, 1H), 7.93 (d, 1H), 7.88-7.65 (m, 2H); ESIMS m/z 211 ([M+H]+), m/z 209 ([M-H]-).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 603-62-3.

Reference:
Patent; DOW AGROSCIENCES LLC; US2011/301178; (2011); A1;,
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Electric Literature of 102359-00-2, 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3-(1H-Indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid A mixture of 5-carboxy-2-oxindole (88.5 mg) (prepared as described in Compound IN-05), indole-2-carbaldehyde (87 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) and piperidine (1 drop) in ethanol (3 mL) was heated in a sealed tube at 95 C. for 4 hours. The mixture was cooled to room temperature. The solid was filtered and acidified with 2N hydrochloric acid. The resulting darker solid was collected by vacuum filtration, washed with cold ethanol and dried in vacuum oven for overnight to give 60 mg (40% yield) of 3-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid as a mustard-colored solid. 1H NMR (360 MHz, DMSO-d6) 12.8 (s, br, 1H, NH), 12.69 (s, 1H, COOH), 11.35 (s, br, 1H, NH), 8.33 (s, 1H), 8.16 (s, 1H), 7.86 (dd, J=1 and 8 Hz, 1H), 7.68 (d, J=8 Hz, 1H), 7.59 (d, J=8 Hz, 1H), 7.28 (t, 1H), 7.21 (s, 1H), 7.08 (t, 1H), 6.99 (d, J=8 Hz, 1H). MS m/z 304 [M]+.

The synthetic route of 2-Oxoindoline-5-carboxylic Acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); 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. 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid

Ethyl 2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanoate (17, n=2):5 Thionyl chloride (3.1 mL, 4-5 eq) was dissolved in CCl4. Then Pht-GABA (2.4 g, 10.3 mmol) was added. The slurry was put on oil bath at ~85 oC and refluxed for 1 h 15 min. Everything dissolved within a few minutes. NBS (1.2 eq., 12.36 mmol, 2.2 g) was added to the warm solution forming yellow slurry. On addition of 3 drops of 40% HBr(aq) everything dissolved and solution became red. Reaction mixture was heated under reflux. Within 1 h of reflux in homogenous mixture turned black. After additional 10 min reaction mixture was cooled down, poured into 15 mL of dry EtOH (exothermic), followed by addition of EtOH (2×15 mL). After 10 min it was evaporated to dryness. Product isolated using column chromatography

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 35197-64-9.

Reference:
Article; Coxon, Fraser; Joachimiak, ?ukasz; Najumudeen, Arafath Kaja; Breen, George; Gmach, Joanna; Oetken-Lindholm, Christina; Way, Rebecca; Dunford, James; Abankwa, Daniel; B?azewska, Katarzyna M.; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 77 – 89;,
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Electric Literature of 199328-10-4,Some common heterocyclic compound, 199328-10-4, name is Methyl Oxindole-5-carboxylate, molecular formula is C10H9NO3, 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.

Step 2: Synthesis of 5-Carboxy-2-oxindole. 5-Methoxycarbonyl-2-oxindole (1 g) and 1 g of sodium hydroxide in 20 mL of methanol was refluxed for 3 hours. The reaction mixture was cooled and concentrated to dryness. The residue was dissolved in water and extracted twice with ethyl acetate. The aqueous layer was acidified with 6 N hydrochloric acid and the precipitated solid collected, washed with water, and dried to give 0.7 g (78%) of the title compound as an off-white solid.

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

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
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Related Products of 56341-37-8, These common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, 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.

EXAMPLE 1Preparation of intermediate E/Z-6-chloro-3-[1-(3-chlorophenyl)-methylidene]-1,3-dihydro-indol-2-one To the mixture of 6-chlorooxindole (16.2 g, 92 mmol) (Crescent) and 3-chloro-benzaldehyde (12.9 g, 92 mmol) (Aldrich) in methanol (109 mL) was added pyrrolidine (6.55 g, 92 mmol) (Aldrich) dropwise. The mixture was then heated at 70 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid (Yield 25.2 g, 94.4%).

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Liu, Jin-Jun; Zhang, Zhuming; US2008/114013; (2008); A1;,
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Synthetic Route of 84807-26-1,Some common heterocyclic compound, 84807-26-1, name is 4-Nitroindoline, molecular formula is C8H8N2O2, 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-{1-[6-(4-nitro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 150 mg (0.470 mmol) TBTU were added to 150 mg (0.44 mmol) 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 75 mg (0.46 mmol) 4-nitro-2,3-dihydro-1H-indole, 100 muL (0.712 mmol) triethylamine in 1.5 mL DMF and the mixture was stirred overnight at RT. The reaction mixture was poured onto 30 mL water. The aqueous phase was extracted with DCM (3*20 mL). The combined organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was dissolved in 3 mL DMF, filtered through a syringe filter and purified by preparative HPLC. The product fractions were combined and lyophilised. Yield: 30 mg (14% of theoretical) ESI-MS: m/z=487 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Nitroindoline, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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., name: 5-Nitroindoline

Example V; 5-nitro-1 -pyrimidin-2-yl-2,3-dihydro-1 H-indole300 mg 5-nitro-2,3-dihydro-1 H-indole are dissolved in 4 ml N-methyl- pyrrolidine. 80 mg NaH (60 % suspension in mineral oil) are added and the mixture is stirred for 15 minutes at ambient temperature. Then 380 mg of 2- bromopyrimidine are added and the mixture is then heated to 600C for 3 hours. It is then diluted with diethyl ether and washed with dilute citric acid solution and saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo. Yield: 410 mg (95 % of theory) Rf value: 0.61 (silica gel: ethyl acetate/petroleum ether 1 :1 )

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/16118; (2009); A1;,
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 150560-58-0 as follows. Recommanded Product: 5-Isopropylindoline-2,3-dione

General procedure: Isatin based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL¡Á4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

According to the analysis of related databases, 150560-58-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Javid, Muhammad Tariq; Rahim, Fazal; Taha, Muhammad; Nawaz, Mohsan; Wadood, Abdul; Ali, Muhammad; Mosaddik, Ashik; Shah, Syed Adnan Ali; Farooq, Rai Khalid; Bioorganic Chemistry; vol. 79; (2018); p. 323 – 333;,
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Adding a certain compound to certain chemical reactions, such as: 2913-97-5, name is N-(2-Oxoethyl)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 2913-97-5, Computed Properties of C10H7NO3

A solution of ammonium acetate (5.40 g) in methanol (50 ml) was added to a solution of Compound 204 (2.00 g) and (1,3-dioxo-1,3-dihydroindol-2-yl) acetaldehyde (2.00 g) in tetrahydrofuran (70 ml), and the mixture was stirred for 3.5 hours at room temperature. The reaction solution to which a saturated aqueous solution of sodium hydrogen carbonate was added was neutralized, and then extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated off. The residue was purified by silica gel column chromatography three times with (hexane:ethyl acetate=40:60 –> 20:80), (chloroform:methanol=95:5), and (chloroform:ethyl acetate=35:65) to yield the title compound (1.90 g) as a light yellow powder (mp: 250.5-255.0¡ãC). 1H NMR (300 MHz, CDCl3) delta ppm: 2.44 (3H, d, J = 0.8 Hz), 5.08 (2H, s), 6.74 (1H, brs), 7.71-7.94 (6H, m), 8.16 (1H, d, J = 8.5 Hz), 9.03 (1H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(2-Oxoethyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1721905; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem