Tag: M.W=100-200

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. 52351-75-4, name is 6-Methoxyindoline-2,3-dione, A new synthetic method of this compound is introduced below., name: 6-Methoxyindoline-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 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; 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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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. 74572-29-5, name is 5-Chloroisoindolin-1-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H6ClNO

[A] 2-(8-Amino-5,6,7,8-tetrahydro-isoquinolin-4-yl)-5-chloro-2,3-dihydro-isoindol-1-one In a 25 mL sealed tube, 5-chloro-2,3-dihydro-isoindol-1-one (80.1 mg, 4.8 mmol), 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-ylamine (intermediate B-12 [A], 999 mg, 4.4 mmol), CuI (200 mg, 1.1 mmol), Cs2CO3 (3.0 g, 9.2 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.4 mL, 3.2 mmol) were dissolved in dioxane (16 mL). The resulting reaction mixture was heated at 150 C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2*125 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (1.2 g, 80%) as a light yellow solid. MS: 314.2 (M+H+).

The synthetic route of 74572-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Aebi, Johannes; Amrein, Kurt; Chen, Wenming; Hornsperger, Benoit; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Wang, Zhanguo; Zhou, Mingwei; US2013/143863; (2013); A1;,
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Application of 114041-16-6, 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. 114041-16-6, name is 5,6-Dimethoxyisoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Compound 8 (70.6 mg, 0.24 mmol) and 5,6-dimethoxyisoindoline(68.5 mg, 0.38 mmol) were dissolved in CH3CN (30 mL), followed by addition of K2CO3 (138.8 mg, 1.00 mmol). The mixture was heated under reflux and stirred at 90 C for 6 h. After cooling and filtration, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate/triethyamine) = 10:10:1, v/v/v) to afford 13(56.8 mg, 59%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): d7.15-7.06 (m, 3H, Ar-H), 6.77 (s, 2H, Ar-H), 6.66 (dd, J = 3.1,0.5 Hz, 1H, Ar-H), 6.52 (d, J = 7.2 Hz, 1H, Ar-H), 4.84 (dt, J = 47.5,4.2 Hz, 2H, F-CH2), 4.37 (dt, J = 27.8, 4.3 Hz, 2H, O-CH2), 4.27 (t,J = 6.7 Hz, 2H, indole N-CH2), 3.87 (s, 10H, O-CH3, Ar-CH2-N), 2.65(t, J = 6.7 Hz, 2H, N-CH2), 2.08-2.05 (m, 2H, CH2). 13C NMR(100 MHz, CDCl3) d (ppm): 152.43, 148.63, 137.94, 131.86,127.08, 122.29, 119.61, 106.14, 103.84, 100.64, 98.63, 82.35(J = 169.2, F-CH2), 67.49 (J = 20.6, O-CH2), 59.32, 56.34, 52.75,44.12, 29.56. ESI-TOF MS calcd for C23H28FN2O3 [M+H]+:399.2084; found: 399.2076.

The synthetic route of 5,6-Dimethoxyisoindoline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Liang; Ye, Jiajun; He, Yingfang; Deuther-Conrad, Winnie; Zhang, Jinming; Zhang, Xiaojun; Cui, Mengchao; Steinbach, Joerg; Huang, Yiyun; Brust, Peter; Jia, Hongmei; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3792 – 3802;,
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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Nitroindoline-2,3-dione

General procedure: A mixture of dimedone (0.140 g, 1 mmol), isatin (0.147 g, 1 mmol) and malononitrile (0.066 g, 1 mmol) was stirred in round bottom flask containing 5 mL of oxalic acid dihydrate:proline LTTM at room temperature for an appropriate time. After completion of the reaction, as indicated by TLC, 10 mL of water was added to the reaction mixture and the insoluble crude product was filtered off. The aqueous layer was evaporatedunder vacuumto recover the LTTM. The crude product was washed with distilled water(5 mL) and recrystallized from ethanol (10 mL).

According to the analysis of related databases, 611-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chandam, Dattatray R.; Mulik, Abhijeet G.; Patil, Dayanand R.; Deshmukh, Madhukar B.; Research on Chemical Intermediates; vol. 42; 2; (2016); p. 1411 – 1423;,
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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A solution of 7-methylindoline-2,3-dione (7.08 g, 44 mmol), NaOH (1.77 g, 44 mmol) and KCl (7.08 g, 95 mmol) in water (80ml) was cooled to 0 C and 33% H2O2 (6.02 mL, 0.66 mmol) was added dropwise over 1.5 hours. After an additional 45 minutes at room temperature the addition of acetic acid (16 mL) caused precipitation of the product. Recrystallization from water gave the title compound (5.26 g, 80%) as a pale brown solid. mp 162 – 164 C (Litt7. 174 – 176 C). 1H NMR (300 MHz, DMSO-d6) delta 7.61 (dd, J = 8.0, 1.3 Hz, 1H), 7.13 (dd, J = 7.1, 1.3 Hz, 1H), 6.45 (dd, J = 8.0, 7.1 Hz, 1H), 2.10 (s, 3H). 13C NMR (75 MHz, DMSO-d6) delta 169.9, 149.6, 134.3, 129.0, 122.9, 114.3, 109.3, 17.7

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 1127-59-9.

Reference:
Article; Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Braeuner-Osborne, Hans; Kristensen, Jesper Langgaard; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3933 – 3937;,
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. 3484-35-3, name is 5-Methylindolin-2-one, A new synthetic method of this compound is introduced below., SDS of cas: 3484-35-3

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (3a-3h, 8a-8f) (0.003 mol) in 1,4-dioxane (15 ml) was added HC(OEt)3 (2 ml) and BF3·Et2O (2 ml). The reaction mixture was heated to 80 C and stirring was continued at the same temperature for 4 h. The resulting 2-ethylthio-3-substituted-5-benzylidene-4-thiazolium fluoroborate (4a-4h, 9a-9f) was precipitated, filtered off, and dried without any additional purification, as starting material for the following reactions. To a mixture of thiazolium fluoroborate (4a-4h, 9a-9f) (0.003 mol) and indolin-2-one (11a-11f) (0.003 mol) in acetonitrile (15 ml) was added triethylamine (0.91 g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at the same temperature. The orange precipitate was collected and washed with ethyl acetate (8 ml). The crude product thus obtained was recrystallized from methanol or acetone to give compound (5a-5s, 10a-10s).

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Shuobing; Zhao, Yanfang; Zhang, Guogang; Lv, Yingxiang; Zhang, Ning; Gong, Ping; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3509 – 3518;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15937-07-2, name is 5,6-Dimethoxyindoline, 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 15937-07-2, Product Details of 15937-07-2

The experimental steps and operations are: at room temperature,18 g of Compound 2 was dissolved in 200 mL of acetonitrile, and the mixture was vigorously stirred in an environment where the container was exposed to air or oxygen, and the reaction was continued.The TLC tracks the reaction until the material completely disappears, which takes approximately 16-24 hours.The crude product was concentrated under reduced pressure on a rotary evaporator, and purified using silica gel column chromatography eluting with petroleum ether ethyl acetate (90:10, v/v).Obtaining Compound 3 as a colorless crystal; placing a single crystal in the receiving bottle. The weight of the compound 3 was 11.5 g, and the yield was 71% (the total yield of the two-step reaction).

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, 5,6-Dimethoxyindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Yantai Liudi Pharmaceutical Technology Co., Ltd.; Yang Jiade; Wang Xiujie; Fan Yulong; Qu Wenchao; Chen Tingting; (14 pag.)CN108484471; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Application In Synthesis of 6-Chlorooxindole

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

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

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
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Indoline | C8H9N – PubChem

Related Products of 6341-92-0, A common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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 117 2-(6-Chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-3-cyclopentyl-N-thiazol-2-yl-propionamide A mixture of sodium hydride (60% in oil, 264 mg) in N,N-dimethylformamide at 0 C. was treated with a solution of 6-chloro-1H-indole-2,3-dione (1.0 g) in N,N-dimethyl formamide (total volume is 25 mL). The reaction mixture was then stirred for 30 min at 0 C. After this time, the reaction mixture was treated with 2-bromo-3-cyclopentyl-propionic acid methyl ester (prepared as in Example 1, 1.55 g) and stirred for another 1 h at 0 C. The reaction mixture was then allowed to warm to room temperature and stirred for 3 h. After this time, the reaction was diluted with water and extracted with methylene chloride. The organic layers were combined and then dried over sodium sulfate, filtered to remove the drying agent and the filterate concentrated in vacuo. The residue obtained was then purified by silica gel column chromatography to afford 2-(6-chloro-2,3-dioxo-2,3-dihydro-indol-1-yl)-3-cyclopentyl-propionic acid methyl ester (1.4 g, 76%).

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

Reference:
Patent; Kester, Robert Francis; US2012/142705; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 61-70-1, These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-2-one, 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 5 L 4-neck flask (equipped with a mechanical stirrer, condenser, N2 inlet and NAOH scrubbing solution) was charged sequentially with carbon disulfide (CS2) (1.5 L), anhydrous aluminum chloride (AIC13) (2.7 mol, 359 g, 6 equiv) and CHLOROACETYL chloride (0.585 mol, 66.1 g (46.6 mL), 1.3 equiv). 1- methyl-1, 3-dihydroindol-2-one (0.45 mol, 66.2 g, 1 equiv) was added portionwise over 1 hour; the addition was accompanied with temperature increase of 20–> 310 C. After the addition of 1-methyl-1, 3-dihydroindol-2-one was complete the reaction mixture was stirred 0.75 hour at which time stirring of the reaction mixture was not possible. The reaction mixture was refluxed for 3.5 hours then cooled to room temperature. The carbon disulfide (CS2) was decanted, the residue cooled in an ice/water bath. The reaction mixture was quenched by very slow addition of ice and water. The resulting tan suspension was stirred overnight at room temperature. The solids was collected, washed with water (4X), dried on the filter for 15 min followed by drying overnight in hood. The product was further dried in a vacuum oven at- 50 C for 24 hours; the product was pulverized and dried in a vacuum oven for an additional 3 hours AT-70 C to give 91.6 g (91%) of 5-(2-CHLOROACETYL)-1- METHYL-1, 3-dihydroindol-2-one of a salmon colored solid, mp 197-200 C.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/37820; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem