Author: Jessica.F

Related Products of 100510-65-4, A common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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.

To a solution of compound 8 (100 mL, compound 7, 23.7 mmol from 5.3 g) at 0 to 5 degrees, a methylene chloride solution of compound 23 (4.0 g, 18.8 mmol) and triethylamine (2.6 mL, 18.8 mmol) was added dropwise. The reaction solution was stirred at room temperature overnight, washed with aqueous sodium bicarbonate solution, washed with water, the organic phase was concentrated under reduced pressure, filtered, and the filter cake was washed with a small amount of dichloromethane, and dried in vacuo to give an off-white solid compound 24 (5.2 g, yield 65.7%).

The synthetic route of 100510-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Ruiming Drug Discovery Co., Ltd.; Zhang Fei; Feng Zixia; (33 pag.)CN110950868; (2020); A;,
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Application of 112656-95-8,Some common heterocyclic compound, 112656-95-8, name is 7-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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.

The solution of 7-nitro-isatin (15) (3 g, 0.016 mol), cyanoacetic acid (1.33 g, 0.016 mol) and piperidine (0.10 ml) in pyridine (15 ml) was refluxed for 30 hours. After cooling to room temperature, concentrated hydrochloric acid (1 ml) and water (10 ml) were added. The product was obtained by extraction with ethylacetate. Organics were dried under sodium sulfate, solvent was removed in vacuum to give 2 g (60 % yield) of (7-nitro-2-oxindole-3-yliden)acetonitrile. mp (exp.) = 224-225 0C. Spectrum NMR 1 (DMSO-d6, delta, ppm, J, Hz): 6.94 (s, 1H), 7.28 (dd, J = 7.45; J = 8.34, 1H); 7.86 (d, J = 7.20, 1H), 8.10 (d, J = 8.59, 1H), 11.33 (s, 1H). Spectrum NMR 13C (DMSO-d6, delta, ppm): 70.99; 117.17; 122.89; 125.25; 130.77; 131.62; 133.82; 138.63; 177.50. IR spectrum (sm-1): 1535; 1598; 1626 (NO2), 1727 (C=O), 2926; 2958 (C=C-H), 3239; 3348 (NH). MS (EI, 70 eV), m/z (I, %): 233 (77, [M*H2O]+), 215 (26, M+), 193 (86), 189 (44), 175 (50), 149 (32), 145 (60), 118 (70), 90 (31), 63 (31), 41 (40), 30 (100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Nitroindoline-2,3-dione, its application will become more common.

Reference:
Article; Zaryanova, Ekaterina V.; Lozinskaya, Nataly A.; Beznos, Olga V.; Volkova, Maria S.; Chesnokova, Nataly B.; Zefirov, Nikolay S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 16; (2017); p. 3787 – 3793;,
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Indoline | C8H9N – PubChem

Related Products of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cooled solution of 2.0 M of lithium tetrahydroborate in tetrahydrofuran (13 mL, 26 mmol) at 5C was added dropwise a solution of 5-amino-l,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (1.0 g, 4.3 mmol) in tetrahydrofuran (50 mL). Gas evolution was noted. The mixture was stirred for 1 hour at 5C then warmed to room temperature and stirred for 24 hours. The mixture was cooled to 5C in a ice/water bath and the reaction was quenched by addition of sodium sulfate decahydrate (3 g). Gas evolution noted. The mixture was stirred for 2 hours at room temperature. The suspension was filtered through a plug of diatomaceous earth and rinsed with with tetrahydrofuran. The filtrate was dried over magnesium sulfate, filtered and evaporated. The residue was purified via flash chromatography (silica gel column and 0%?20% methanol: dichloromethane). 2-Methyl-2,3-dihydro-lH-isoindol-5-ylamine was isolated as an orange solid (0.271 g, 43%). 1H NMR (400 MHz, (D3C)2SO, delta, ppm): 6.82 (d, J=I .9 Hz, IH), 6.41 (s, IH), 6.37 (d, J=8.1 Hz, IH), 4.86 (br s, 2H), 3.64 (s, 2H), 3.62 (s, 2H), 2.42 (s, 3H). MS = 149 (MH)+.

The synthetic route of tert-Butyl 5-aminoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON, INC.; CURRY, Matthew A.; DORSEY, Bruce D.; DUGAN, Benjamin J.; GINGRICH, Diane E.; MESAROS, Eugen F.; MILKIEWICZ, Karen L.; WO2010/141796; (2010); A2;,
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Application of 13220-46-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13220-46-7 name is 4-Methylindolin-2-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

5-Chloro-4-methyl-2-oxindole A suspension of 3.0 g of 4-methyl-2-oxindole was stirred in 50 mL of acetonitrile at room temperature while 3.3 g of N-chlorosuccinimide was added in portions. Trifluoroacetic acid (1 mL) was then added. The suspension was stirred at room temperature for 3 days during which time solid was always present. The white solid was collected by vacuum filtration, washed with a small amount of cold acetone and dried overnight in a vacuum oven at 40 C. to give 2.5 g (68%) of 5-chloro-4-methyl-2-oxindole.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methylindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H9NO3

General procedure: In a double-necked round-bottom flask (100 mL) wasadded a mixture consisting of nucleobase (0.01 mol),alcohol (0.012 mol), TsCl (2.86 g, 0.015), TEA (1.01 g,0.01 mol) and K2CO3 (1.38 g, 0.010 mol) in bmim[Br](10 mL). The flask was immersed in an oil bath, kept at80 C and stirred for the time when TLC indicated no furtherprogress in the conversion (Tables 4, 5, 6). The mixturewas then diluted with water (200 mL) and extracted withEtOAc (3 × 50 mL). The organic layer was dried (Na2SO4)and evaporated to afford the crude product which was purifiedby traditional column chromatography on silica geleluting with proper solvents.

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 3891-07-4.

Reference:
Article; Rad, Mohammad Navid Soltani; Behrouz, Somayeh; Zarenezhad, Elham; Kaviani, Narjes; Journal of the Iranian Chemical Society; vol. 12; 9; (2015); p. 1603 – 1612;,
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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. 2058-74-4, name is 1-Methylisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 2058-74-4

General procedure: A mixture of isatin (1 mmol), malononitrile (1 mmol) and dimedone (1 mmol) was stirred at room temperature in the presence of SnO2 nanoparticles and 2 mL of EtOH. The reaction progress was monitored by TLC (n-hexane/ethyl acetate, 2:1 ratio). After that, the resulted mixture (containing the solid product and nano catalyst) was dissolvedin acetone and filtered for separation of the catalyst. Finally, the product 5a was obtained after evaporation of acetone and for further purification recrystallized from EtOH.

The synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moradi, Leila; Ataei, Zeynab; Zahraei, Zohreh; Journal of the Iranian Chemical Society; vol. 16; 6; (2019); p. 1273 – 1281;,
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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. 39755-95-8, name is 5-Methoxyisatin, A new synthetic method of this compound is introduced below., Product Details of 39755-95-8

General procedure: Fe 3 O 4 /COSbeta-CD-SO 3 H NPs (V) (0.02 g) were added to a mixture of isatin (1 mmol, 0.147 g), 5,5-dimethylcyclohexane-1,3-dione (dimedone) (1 mmol, 0.140g), and malononitrile (1mmol, 0.066g) in water (4mL). The mixture was magnetically stirred at 50C, for 20min. Reaction progress was monitored by TLC (n-hexane:EtOAc, 3:1). Upon reaction completion, the catalyst was removed by an external magnet, washed with water (10mL), and dried overnight to be ready for the next run. The formed solid was filtered off, washed with warm water, then dried to obtain pure products (0.328g, 98%).

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mohammadian, Narges; Akhlaghinia, Batool; Research on Chemical Intermediates; vol. 45; 10; (2019); p. 4737 – 4756;,
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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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C14H13NO3

The title compound from Preparative Example 23 Step A (1.54 g, 8.23 mmol) was dissolved in ethanol (50 mL) and the title compound from Step C above (2 g, 8.23 mmol) was added. The mixture was stirred at room temperature for 1 h to become a suspension. The solvent was removed to afford the title compound as an off-white solid (3.3 g, quant.).1H-NMR (400 MHz, DMSO-d6): delta=2.00-2.18 (m, 3H), 2.27-2.43 (m, 2H), 2.50-2.63 (m, 2H), 3.30-3.38 (m, 1H), 4.46 (tt, 1H), 7.00 (d, 1H), 7.18 (d, 1H), 7.62 (t, 1H), 7.93-8.00 (m, 4H), 10.1 (s, 1H)

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; AC Immune, S.A.; US2011/280808; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

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

Reference:
Article; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 446292-08-6, A common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, molecular formula is C22H19N3O6, 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.

210.7 g (0.5 mol) of (S)-2-{[2-oxo-3-(4-(3-oxomorpholine)benzene] prepared in Example 7 was added to the reaction flask.Based on oxazolidine-5-yl]methyl}isoindole-1,3-dione (formula VII), 1500 ml of anhydrous ethanol,500 ml of a 30% aqueous solution of methylamine was stirred and heated to 40C to 60C for 8 hours.TLC control (dichloromethane:methanol = 20:1, volume ratio) reaction is complete, with 10% hydrochloric acid to adjust the pH to between 1-2, precipitated a lot of white solids, cooled to about 15 C, stirred for 2 hours, filtered The filter cake was washed with 300 ml of anhydrous ethanol and dried under reduced pressure to obtain 147.0 g of a white solid (compound of formula VIII) with a molar yield of 89.7% and an HPLC purity of 98.7%.

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Peking University Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Xu Hong; Fan Yang; Zhang Zheng; Wang Wei; Ren Juan; (14 pag.)CN105085431; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem