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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8N2O2

Step A-Preparation of 1-(1-methyl(4-piperidyl))-6-nitroindoline 6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane, N-methyl-4-piperidone (5 g) was added to the mixture, followed by 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) was added to the reaction mixture and stirred for 1 h. The resulting mixture was separated by separation funnel, the organic layer was extracted once with saturated NaHCO3 solution and once with brine. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford an orange oil. MS: 262 (M+1). Calc’d. for C14H19N3O2-261.32.

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US6878714; (2005); B2;,
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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,7-Dimethylindoline-2,3-dione

General procedure: A mixture of isatin derivative (1.0 mmol), trans-4-hydroxy-L-proline (0.131 g,1 mmol), and CTAB (4 mmol) in water (50mL) was stirred at 80 C for 30 min. After completion of the reaction (monitored by TLC), the contents were filtered and the residue was washed thoroughly with water until free from CTAB. Finally, the residue was crystallized from a chloroform-petroleum ether mixture to afford the desired products in excellent yields. The characterizations of the products were accomplished by spectroscopic analysis (1H, 13C NMR, FTIR, and ESI-mass) and also by comparison of the data reported in the literature.

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; Naskar, Subhendu; Roy, Suprakash; Sarkar, Swarbhanu; Synthetic Communications; vol. 44; 11; (2014); p. 1629 – 1634;,
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. 15861-23-1, name is Indoline-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H8N2

The 5 – cyano – indoline (1.00 g, 6. 94 mmol) and TEA (2.88 ml, 20.8 mmol) dissolved in DCM (30 ml) in, adding 3 – bromo – benzenesulfonyl chloride (1.95 g, 7.63 mmol) At room temperature overnight and for. Water quenching reaction, divide the DCM layer, for extracting the alternating layer twice twice DCM, the combined DCM layer turns on lathe does after drying, a yellow solid intermediate 1 a (2.26 g, yield: 90%) .

According to the analysis of related databases, 15861-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chengdu Xiandao Pharmaceutical Development Co., Ltd.; Li Jin; Wang Wei; Chu Hongzhu; Lv Kaizhi; Liu Lichuan; Nong Yunhong; Chen Wei; (17 pag.)CN110256416; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 114041-16-6,Some common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, molecular formula is C10H13NO2, 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 17 N-(2-tert-butoxybenzyl)-6-(5,6-dimethoxyisoindolin-2-yl)-N-(pyridin-2-ylmethyl)hexan-1-amine [13] The same procedure as described for compound 11 was applied to starting material 10 (0.428 g, 0.988 mmol) and 5,6-dimethoxyisoindoline (0.175 g, 0.975 mmol). Purification was carried out on a silica gel TLC plate that was developed in with a 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as pale yellow oil (60%). 1H NMR (CDCl3) delta 8.446 (dd, 1H, Ar), 7.72 (m, 3H, Ar), 7.062 (m, 2H, Ar), 6.981 (ddd, 2H, Ar), 6.888 (s, 2H, Ar), 3.816 (s, 4H, -CH2-CH2-), 3.792 (s, 6H, -OCH3-), 3.714 (s, 2H, -CH2-), 3.637 (s, 2H, -CH2-), 2.611 (t, 2H, -CH2-), 2.436 (t, 2H, -CH2-), 1.503 (m, 4H, -CH2-CH2-), 1.319 (s, 9H, -C(CH3)3), 1.275 (m, 4H, -CH2-CH2-). Mass Spec.=531.73 (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 5,6-Dimethoxyisoindoline, its application will become more common.

Reference:
Patent; President and Fellows of Harvard College; US2012/269724; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2, A common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, 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.

The intermediate compound 4 (0.05 mol) was slowly added to 30 ml of 0 C concentrated H2SO4,Control the temperature does not exceed 12 C; added, ice bath conditions slowly add mixed acid (fuming nitric acid / concentrated sulfuric acid = 1/1) 15ml, remove the ice bath, 55 C heating and stirring for 12 hours. The reaction solution was poured into 3 times of ice water, and the mixture was stirred while stirring, and the solid was filtered. The filter cake was washed three times with 100 ml of water and recrystallized from 95% ethanol to give intermediate 11 as a pale yellow solid in 16%

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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: A mixture of phthalic anhydride (1 mmol), isatin (1 mmol), malononitrile(1 mmol), hydrazine (1 mmol), and Fe3O4dipyridineMNPs (0.0008 g) was stirred at room temperature under solvent free conditions for 50 min. Upon completion, the progress of the reaction was monitored by TLC when the reaction was completed,EtOH was added to the reaction mixture and the Fe3O4methyleneMNPs was separated by external magnet. Then the solvent was removed from solution under reduced pressure and the resultingproduct purified by recrystallization using ethanol.

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

Reference:
Review; Sadeghzadeh, Seyed Mohsen; Nasseri, Mohammad Ali; Catalysis Today; vol. 217; (2013); p. 80 – 85;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3485-84-5, The chemical industry reduces the impact on the environment during synthesis 3485-84-5, name is N-Vinylphthalimide, I believe this compound will play a more active role in future production and life.

General procedure: General procedure B: To a dried glass tube, Togni reagent 2 (99mg, 0.3mmol, 1.5equiv), (L3)CuBr (10mg, 0.02mmol, 0.1equiv) and CH3CN (1.0mL) were added under N2 atmosphere, followed by substrate 1 (0.2mmol, 1.0equiv) and TMSCN (54muL, 0.4mmol, 2.0equiv). After the reaction mixture was stirred at room temperature for 0.5h, the mixture was concentrated under vacuum. The residue was purified by column chromatography on silica gel with a gradient eluent of petroleum ether and ethyl acetate to afford the product. General procedure B: Pale yellow solid; 46.6mg, 87%; 1H NMR (400MHz, CDCl3): delta 7.94 (dd, J=5.2, 3.2Hz, 2H), 7.82 (dd, J=5.2, 3.2Hz, 2H), 5.54 (dd, J=8.4, 5.2Hz, 1H), 3.33-3.17 (m, 1H), 3.06-2.94 (m, 1H); 13C NMR (100MHz, CDCl3): delta 165.5, 135.1, 131.0, 124.3, 124.0 (q, J=276.3Hz), 114.0, 35.0 (q, J=30.0Hz), 33.9 (q, J=3.8Hz); 19F NMR (376MHz, CDCl3): delta -65.1 (t, J=10.0Hz); HRMS (EI), calcd. for C12H7F3N2O2 268.0460 [M]+, found 268.0456.

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, N-Vinylphthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liang, Zhaoli; Wang, Fei; Chen, Pinhong; Liu, Guosheng; Journal of Fluorine Chemistry; vol. 167; (2014); p. 55 – 60;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-one, 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 16800-68-3, Recommanded Product: 16800-68-3

General procedure: 1a (35 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 mL THF was added using a syringe. The reaction mixture was stirred 15 min,and then 6 ( 0.2 mmol, 1.0 eq) was added, and the reaction was stirred at room temperature for 10 hours. the solvent was removed in vacuo and the residue was purified by silica gel using a propereluent (EtOAc/Hexane) to afford the desired products.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Acetylindolin-3-one, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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. 5428-09-1, name is 2-Allylisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5428-09-1

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3¡Á20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

The synthetic route of 5428-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 317-20-4, 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. 317-20-4 name is 7-Fluoroisatin, 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.

Step 1a: Preparation of 7-fluoro-1-methyl-1H-indole-2,3-dione (6) 7-Fluoro-1H-indole-2,3-dione (5, prepared according to the method of Gassman as described in U.S. Pat. No. 4,188,325, 3.00 g, 0.182 mol), iodomethane (3.40 ml, 0.545 mol) and potassium carbonate (4.92 g, 0.0363 mol) in DMF (15 ml) are stirred at room temperature for 1 hour. The reaction mixture is diluted with cold water and the resulting precipitate filtered and dried to give the title compound as a solid. HPLC r.t. 4.01 min; MS for C9H6FNO2 m/z 180.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Fluoroisatin, and friends who are interested can also refer to it.

Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail; Luehr, Gary; US2006/229349; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem