Tag: M.W=100-200

6341-92-0, name is 6-Chloroisatin, 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

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, mp 196-198 C.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4721712; (1988); A;,
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These common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, 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. Application In Synthesis of 5-Chloro-7-methylindoline-2,3-dione

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

The synthetic route of 5-Chloro-7-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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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;,
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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. 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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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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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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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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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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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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Synthetic Route of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of phthalimide (41.14 g, 0.30 mol) and distilled water (100 mL) was stirred for 10 min at room temperature. After addition of formaldehyde solution (40%, 27 mL, 0.36 mol), the resulting solution was refluxed for 1.5 h. After cooling to 0-5 C, the resulting precipitate was collected by filtration, washed with cold water (0-5 C, 200 mL) and dried in air to give the corresponding N-hydroxymethylphthalimide (51.01 g, 96% yield).(0010)A solution of thionyl chloride (23.0 mL, 37.7 g, 0.32 mol) in dichloromethane (50 mL) was slowly added to a mixture of the resulting N-hydroxymethylphthalimide and dichloromethane (550 mL) and N,N-dimethylformamide (350 mL) during 30 min at room temperature with stirring. The resulting mixture was further stirred for 2 h at room temperature. After cooling to 0 C, water (200 mL) was added slowly. And the solution was neutralized to pH 6.7-7.0 by using saturated aqueous NaHCO3 solution. The organic layer was separated and then was dried over anhydrous magnesium sulfate. After evaporation of the solvent under the reduced pressure, the residue was washed with n-hexane (100 mL) to give N-chloromethylphthalimide (51.4 g, 93% yield).(0011) N-Chloromethylphthalimide (51.0 g, 0.26 mol) was dissolved in acetone (500 mL) and potassium O-ethyl xanthate (43.9 g, 274 mmol) was added portionwise in an ice water bath under stirring. The resulting solution was further stirred for 10 h at room temperature. After removal of the solvent, the residue was dissolved in dichloromethane. The resulting solution was washed with water and dried over sodium sulfate. After removal of the solvent under the reduced pressure, pale yellow solid was obtained and recrystallized from ethyl acetate to afford the xanthate 1 as colorless crystals 67.2 g, 92% yield, mp: 99-100 C. Lit.20 mp: 94-95 C. 1H NMR (CDCl3, 400 MHz) (delta, ppm) 1.47 (t, J=7.1 Hz, 3H, CH3), 4.68 (q, J=7.1 Hz, 2H, CH2), 5.34 (s, 2H, CH2), 7.75 (dd, J=5.5, 3.1 Hz, 2H, ArH), 7.88 (dd, J=5.5, 3.1 Hz, 2H, ArH). 13C NMR (CDCl3, 100 MHz) (delta, ppm) 13.7, 41.2, 70.5, 123.6, 131.8, 134.4, 166.6, 210.2.

The chemical industry reduces the impact on the environment during synthesis 2-(Chloromethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Huang, Zhongyan; Xu, Jiaxi; Tetrahedron; vol. 69; 3; (2013); p. 1050 – 1056;,
Indoline – Wikipedia,
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