Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, 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 1336963-95-1, Computed Properties of C8H3BrFNO2

In a solution of compound 2 (2.80 g, 11.48 mmol) in 50 ml of ethanol,Hydrazine hydrate (85%, 0.5 mL) was added under a nitrogen atmosphere,After refluxing for thirty minutes,There is a yellow product after precipitation by suction after drying,Was dissolved in 50 ml of ethanol,T-BuOK (4.03 g, 35.90 mmol) was added,After refluxing for 2 h, the reaction mixture was poured into water,The pH of the system was adjusted to 2 with hydrochloric acid,After extraction with ethyl acetate,Washed,Saturated salt water washing,After drying, distillation under reduced pressure.After the column by silica gelTo give the title compound 3 (1.49 g, yield 56%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Peking University; Pei, Jian; Lei, Ting; Dou, Jinhu; (29 pag.)CN103804271; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 5428-09-1 as follows. name: 2-Allylisoindoline-1,3-dione

The title compound was prepared by utilising Ni(dppp)Br2 (32 mg,50.0 mumol, 10 mol%), zinc powder (6.6 mg) and zinc iodide (32 mg,100 mumol, 20 mol% each). These materials were suspended in dichloromethane(0.3 mL) then Ph2PH solution (0.125 M in dichloromethane,0.2 mL, 25.0 mumol, 5 mol%) was added. 2-Allylisoindoline-1,3-dione (94 mg, 0.502 mmol, 1.0 equiv) was added at ambient temperatureand the reaction mixture was stirred for 18 h. Workup accordingto the general procedure and purification by flash columnchromatography (n-pentane/tert-butyl methyl ether, 20:1) gave 6d asa single E-isomer. Yield: 80 mg (0.426 mmol, 85%); yellow solid.1H NMR (300 MHz, CDCl3): delta = 7.87-7.83 (m, 2 H), 7.75-7.70 (m, 2 H),6.64-6.53 (m, 2 H), 1.84 (d, J = 5.0 Hz, 3 H).13C NMR (76 MHz, CDCl3): delta = 168.8, 134.4, 131.9, 123.6, 118.5, 118.3,16.4.

According to the analysis of related databases, 5428-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Weber, Felicia; Steinlandt, Philipp S.; Ballmann, Monika; Hilt, Gerhard; Synthesis; vol. 49; 2; (2017); p. 440 – 450;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 169037-23-4, The chemical industry reduces the impact on the environment during synthesis 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, I believe this compound will play a more active role in future production and life.

To a solution of 5-trifluoromethoxyisatin (12A, 0.46g, 2.00mmol) in CH2Cl2 (15mL) was added mCPBA (70% pure, 0.54g, 2.2mmol). The resulting solution was allowed to stir for 30 minutes. A solid precipitate formed and was filtered, rinsed with CH2CI2, and dried to yield compound 12B as a solid (0.39g, 79%).

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-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2009/143049; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89-40-7, name is 5-Nitroisoindoline-1,3-dione, 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 89-40-7, Quality Control of 5-Nitroisoindoline-1,3-dione

To a solution of 5-nitro-1H-isoindole-1,3(2H)-dione (1.0 g, 5.2 mmol) in dry THF (15 mL) was added 10% Pd/C (0.2 g). The mixture was hydrogenated at 30-40 psi for 17 h. The catalyst was filtered, and the filtrate was evaporated under vacuo to give 0.5 g (59.3%) of 5-amino-1H-isoindole-1,3(2H)-dione as a yellow colour solid.

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-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-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.

An oven-dried screw cap test tube was charged with a magnetic stir bar, 5-nitroisatin (1; 0.192 g, 1 mmol), malononitrile (2; 0.073 g,1.1 mmol), trisodium citrate dihydrate (0.029 g, 10 mol % as organo catalyst),and EtOH:H2O (1:1 v/v; 4 mL) in a sequential manner; the reaction mixture was then stirred vigorously at room temperature for about 20 min. After that, ethyl acetoacetate (3; 0.130 g, 1 mmol)was added to the stirred reaction mixture, and the stirring was continued for 3 h [15]. The progress of the reaction was monitoredby TLC. On completion of the reaction, a solid mass precipitated out that was filtered off followed by washing with aqueous ethanol to obtain crude product. It was purified just by recrystallization from ethanol without carrying out column chromatography. The structure of ethyl 2′-amino-3′-cyano-6′-methyl-5-nitro-2-oxospiro[indoline-3,4′-pyran]-5′-carboxylate (4) was confirmed by analytical as well as spectral studies including FT-IR, 1H NMR, 13C NMR,and TOF-MS.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindoline-2,3-dione, its application will become more common.

Reference:
Article; Sharma, Sakshi; Brahmachari, Goutam; Banerjee, Bubun; Nurjamal, Khondekar; Kumar, Abhishek; Srivastava, Ambrish Kumar; Misra, Neeraj; Pandey, Sarvesh Kumar; Rajnikant; Gupta, Vivek K.; Journal of Molecular Structure; vol. 1118; (2016); p. 344 – 355;,
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. 110568-64-4, name is 6-Nitroisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Nitroisoindolin-1-one

To a solution of 5-nitro-2,3-dihydro-1H-isoindol-1-one (60 mg, 0.337 mmol) in methanol (20 mL) was added 50 mg of 10% Pd on carbon. The mixture was hydrogenated (with a balloon) for 1 hour. Filtration through Celite followed by concentration led to 38 mg of 5-amino-2,3-dihydro-1H-isoindol-1-one as a tan 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:
Patent; Wyeth; US2010/15141; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 100487-74-9, name is 6-Chloro-5-fluoroindolin-2-one, molecular formula is C8H5ClFNO, 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. name: 6-Chloro-5-fluoroindolin-2-one

EXAMPLE 86a; Preparation of intermediate of E/Z-2-[4-chloro-2-(6-chloro-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-ethyl-butyric acid methyl ester; To the mixture of 6-chloro-5-fluoro-1,3-dihydro-indol-2-one (500 mg, 2.7 mmol) and 2-(4-chloro-2-formyl-phenoxy)-2-ethyl-butyric acid methyl ester (844 mg, 2.97 mmol) in methanol (5 mL) was added pyrrolidine (95 mg, 1.35 mmol) dropwise. The mixture was then heated at 70 C. for 1 h. After cooled to room temperature, the mixture was partitioned between EtOAc and diluted HCl solution. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated to give the crude product as a red-yellow solid, which was used for the next step reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 100487-74-9, its application will become more common.

Reference:
Patent; Chen, Li; Han, Xingchun; He, Yun; Yang, Song; Zhang, Zhuming; US2009/163512; (2009); 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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4N2O4

4-Nitro-2-(3-oxobutyl)isoindoline-1,3-done (1) To a solution containing 3-nitrophthalimide (5.00 g; 26 mmol) in ethyl acetate (30 mL), methyl vinyl ketone (2.8 mL; 33 mmol; 1.25 equ.) is added dropwise. After a few minutes of stirring, 760 muL of triton B (Benzyltrimethylammonium hydroxide, 40% in water) are added. The reaction medium is refluxed for 12 hours. After cooling, the solvents are removed under reduced pressure and the solid residue is recrystallized from absolute ethanol in order to obtain the compound 1 as a yellow solid with a yield of 85%. MP: 122 C.; IR (ATR-Ge v cm-1): 1715 (C=O ketone), 1538 (C=C arom), 1373 (N=O2), 1127 (C-C); 1H NMR (CDCl3; 250 MHz) delta8.19-8.07 (m, 2H), 7.93 (dd, J=7.1 Hz, J=8.5 Hz, 1H), 3.98 (t, J=7.3 Hz, 2H), 2.91 (t, J=7.3 Hz, 2H), 2.20 (s, 3H); 13C NMR (CDCl3; 63 MHz) delta205.7 (Cq), 165.6 (Cq), 162.9 (Cq), 145.2 (Cq), 135.6 (CH), 134.2 (Cq), 128.7 (CH), 127.2 (CH), 123.9 (Cq), 41.2 (CH2), 33.8 (CH2), 30.1 (CH3). MS (IS) m/z: 263.0 [M+H]+

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 603-62-3.

Reference:
Patent; UNIVERSITE D’ORLEANS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.); US2012/95022; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 181140-34-1, 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. 181140-34-1 name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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.

General procedure: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of (R)-(-)-N-(2,3-epoxypropyl)phthalimide 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Article; Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir; Tetrahedron Asymmetry; vol. 22; 5; (2011); p. 541 – 549;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 15861-23-1, 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 15861-23-1 as follows.

The compound of Part A (0.1 g, 0.694 mmol) was dissolved in 1,2-dichloroethane (DCE) (2.5 mL) and a solution of the compound of Part B (80 mg, 0.33 mmol) in DCE (1.5 mL) was added. This mixture was stirred for 10-15 min, then treated with sodium triacetoxyborohydride (0.1 g, 0.48 mmol) and stirred overnight at rt under N2. Reaction was quenched by addition of water and 1N NaOH, then extracted 3× with CH2Cl2. Combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 4:1) provided the product (0.105 g, 86%). 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, 1H, J=7.5 Hz), 7.50-(t, 1H, J=7.5 Hz), 7.41 (t, 1H, J=7.5 Hz), 7.34-7.30 (m, 2H), 7.23-7.11 (m, 4H), 5.99 (d, 1H, J=8.4 Hz), 4.08 (dd, 2H, J=24.2, 15.8 Hz), 3.59 (s, 3H), 3.33 (m, 2H), 2.91 (t, 2H, J=8.4 Hz). LRMS m/z 369.0 (M+H)+ (API+). HRMS Calcd. for C24H21N2O2: 369.1603. Found: 369.1580.

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; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem