Category: indolines-derivatives

Reference of 89-40-7, 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. 89-40-7, name is 5-Nitroisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-Nitrophthalimide (LOOGR) was taken into a hydrogenation vessel and dissolved using 600ML OF DIMETHYLFORMAMIDE. Raney nickel catalyst (20gr, wet) was added to the solution and hydrogenated initially at 20-30C under 20-40psi pressure. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50C. After the hydrogenation is over the reaction mixture was filtered while hot and the catalyst removed by filtration. Dimethylformamide was removed from the filtrate under reduced pressure at 60-80C. Water (500ML) was added to the residue and the mixture stirred for 20-30MIN. The product was isolated by filtration and dried at 60-70C to get a yellow crystalline solid of 4-aminophthalimide (82gr, 97%). Melting point: 293-5C.

The synthetic route of 5-Nitroisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 5394-18-3

To a solution of N-(4-bromobutyl)phthalimide (8g, 0.03mol) in ethanol (50ml) was added morpholine (2.97ml, 0.034mol) and triethylamine (7.9ml, 0.06mol). The reaction was then refluxed under N2 atmosphere for 2Oh after which LC-MS indicated the clean formation of 2- [4-(4-morpholinyl)butyl]-1 H-isoindole-1 ,3(2H)-dione. The reaction mixture was cooled to ambient temperature followed by the addition of hydrazine hydrate (3.26ml, 0.057mol). The reaction mixture was brought up for reflux again for 30min during which a white precipitate was formed. The reaction mixture was cooled to room temperature before the white precipitate was filtered and the filtrate passed through an SCX column (eluting with 100% methanol followed by 10% 2M ammonia in methanol) to afford 4-(4-morpholinyl)butyl]amine (1.8g, 41%).; 4-(4-Morpholinyl)butyl]amineA solution of morpholine (3ml, 34.9mmol), N-(4-bromobutyl)phthalimide (8g, 29mmol) and triethylamine (8ml, 58mmol) in ethanol (55ml) was refluxed for 16h, by which the LC-MS showed reaction completion. The reaction was cooled to room temperature. Ethanol (10ml) and hydrazine hydrate (6ml, 58mmol) were added and the mixture refluxed for 20min, by which a white solid crashed out. The reaction was filtered and the filtrate passed through SCX with methanol followed by 10% 2M ammonium hydroxide in methanol. The latter fractions eluted with 10% ammonium hydroxide in methanol were combined and concentrated in vacuo to afford a bright yellow oil (3g). ELSD LC-MS, (MH+=I 59).

According to the analysis of related databases, 5394-18-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/71577; (2009); A1;,
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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. 20876-36-2, name is 5-Aminoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H8N2O

153 mg (0.490 MMOL) (5-Bromo-2-chloro-pyrimidin-4-yl)-phenethyl-amine was taken into 500 OL 1,4 dioxane with 140 DL (1.00 MMOL) diisopropylethylamine and 80 mg (0.539 mmol) 5-amino-1, 3-dihydro-indol-2-one. The reaction was allowed to heat to 110 C for sixteen hours. The resulting brown glass was taken into 92.3 : 7: 0.7 CHCI3 : CH30H : NH40H and washed with 1 N sodium hydroxide. The organic layer was dried over magnesium sulfate and evaporated directly onto silica gel. This adsorbed compound was purified via column chromatography (97.8 : 2: 0.2 CHCI3 : CH30H: NH40H) over silica to isolate the major product. During evaporation of the major fractions, a white precipitate is noted. Filtration of this precipitate prior to mLete evaporation afforded the title compound in 6percent yield as a white solid. CZOHBRNSO : MS: 424.2/426. 2 (MH+) ;’H NMR (D6-DMSO) 10.20 (s, 1 H), 9.01 (s, 1 H), 7.93 (s, 1 H), 7.52 (s, 1 H), 7.44 (d, J = 8.4 Hz, 1 H), 7.28-7. 16 (m, 5 H), 6.97 (m, 1 H), 6.65 (d, J=8. 3HZ, 1 H), 3.56 (m, 2 H), 3.31 (s, 2 H), 2.82 (t, J = 7.9 Hz, 2 H) ppm.

The synthetic route of 20876-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/56786; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, name: 7-Fluoroisatin

Description 17: 8-Fluoro-3-methyl-2-phenylquinoline-4-carboxylic Acid KOH (88 g, 1560 mmol) in water (400 mL) was added over 30 min. to a suspension of 7-fluoroisatin (64.4 g, 390 mmol) in ethanol (200 mL). Propiophenone (51.9 mL, 390 mmol) was added and the mixture was heated under reflux for 24 h. The mixture was cooled, and hydrochloric acid (conc., 128 mL, 1404 mmol) then acetic acid (11.16 mL, 195 mmol) were added. The mixture was stirred at RT for 16 h. and the solid was collected, washing with water (600 mL), ethanol (200 mL) and hexane/Et2O (1:1, 400 mL). The solid was flushed with toluene (3*500 mL) and dried in vacuo to give the title compound as an off-white solid (91.44 g, 325 mmol, 83%). 1H NMR (500 MHz, DMSO-d6) delta 14.4 (1H, br s), 7.70-7.45 (8H, m), 2.40 (3H, s)

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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Carling, William Robert; Elliott, Jason Matthew; Mezzogori, Elena; Russell, Michael Geoffrey Neil; Williams, Brian John; US2009/54440; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 667463-64-1, 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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-4.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HC1. The organic layer is dried over MgS04 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001 003.

The synthetic route of 6-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRUNDL, Marc; MORSCHHAEUSER, Gerd; OOST, Thorsten; PAUTSCH, Alexander; WO2014/140078; (2014); 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., Safety of 5-Nitroindoline

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 769965-95-9, The chemical industry reduces the impact on the environment during synthesis 769965-95-9, name is 5′-Fluorospiro[cyclopropane-1,3′-indolin]-2′-one, I believe this compound will play a more active role in future production and life.

A sample of 5-fluoro-siprocyclopropyloxindole (172 mg, 97 jimol) was cooled in an ice/water bath and treated with a 1.0 M solution of LAH (1.94 ml, 1.9 mmol). The reaction was stirred at room temperature for 15 minutes and then at 50 C for 3 hours and finally was cooled back down with an icelwater bath. The reaction was treated with 1 M NaOH (1.9 mL) followed by water (1.9 mL). The reaction was filtered over celite and dried over MgS04. After filtration, the solvent was removed and the crude material of 5-fluoro- siprocyclopropylindoline was used without purification.

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, 5′-Fluorospiro[cyclopropane-1,3′-indolin]-2′-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; IRM LLC; WO2005/34848; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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

a) Preparation of 5-bromopentylphthalimide Potassium phthalimide (5.4 mmoles) was added to a solution of 1,5-dibromopentane (3.72 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80C approx. under stirring. After 2 hours, water was added and the solution was repeatedly extracted with ether. The collected organic phases were washed with water, dried on Na2SO4 and evaporated under reduced pressure to give a solid (4.50 g), which was purified by chromatography on silica gel (Etp/Et2O 8:2) yielding 2.38 g of a white solid. Yield 68%.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C9H6ClNO2

A mixture of 2- (1-benzyl-2-oxoindol-3-yl) acetic acid67.4 mg (0.24 mmol),5-chloro-1-methyl isatin 39 mg (0.2 mmol)N, N’-2- (7-benzo benzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate (106.4 mg, 0.28 mmol)Triethylamine 50.6 mg (0.5 mmol)And 2 mL of tetrahydrofuran were placed in a 25 mL two-necked flask,Reaction at 0 C for 6 h,The reaction solution was concentrated,Eluting with a mixed solvent of petroleum ether: ethyl acetate ratio of 3: 1 as elution column,Collecting the eluted fraction of all the products detected,The solvent was removed by rotary distillation to give 82.4 mg of product,The yield was 90% and the Dr value was 4: 1.

The synthetic route of 60434-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Du Ding; Cao Jing; Dong Shuding; (14 pag.)CN106749295; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6941-75-9, 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 6941-75-9 as follows.

As an example of a synthesis method of core Formula VIi-VIj, 4-bromophthalimide(25) can be treated with a reducing agent (e.g., BF OEt followed by BH THF) in an appropriate solvent (e.g., tetrahydrofuran, THF) for the appropriate length of time at the appropriate temperature, to yield 4-bromoisoindoline, 26. The appropriate temperature and appropriate length of time are determined by referenece to Houben-Weyl 4th Ed. 1952, Methods of Organic Synthesis, Thieme, Volume 21.; 5-bromoisoindoline-l,3-dione (5 g, 22.1 mmol) is dissolved in anhydrous THF (30 ml), treated with BF3 OEt2 (6.667 ml, 132.7 mmol) is added and the reaction was stirred at ambient temperature for 30 minutes. To the reaction mixture 1.0M BH3 THF complex (176.94 ml, 525.3 mmol ) is added and the reaction is heated to 4O0C for 36 h. The progress of the reaction is followed by LC/MS. After completion, the reaction mixture is cooled to ambient temperature and quenched with MeOH (6 ml, drop wise) until the bubbling ceases. Then 2N HCl in water (-40 ml, 80 mmol) are added and the mixture is refluxed for 3 h. The reaction is then cooled to ambient temperature and is washed with diethyl ether (2 x 40 ml). The water layer is brought to pH 14 with 6N NaOH (aq) and extracted with ethyl acetate (3 x 100 ml). The combined organic extracts are dried over anhydrous Na2Stheta4 and solvent is removed under reduced pressure to yield 5-bromoisoindoline (68%), (m/z 413[MH+]).

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem