Author: Jessica.F

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 65435-04-3 as follows. Safety of 5-(2-Chloroacetyl)indolin-2-one

A suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 ML pyridine at 80 to 90 C. for 3 hours then cooled to room temperature.. The precipitate was collected by vacuum filtration and washed with 20 ML ethanol.. The solid was dissolved in 90 ML 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours.. The mixture was cooled to room temperature and acidified to PH 2 with 0.5 N hydrochloric acid.. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.. After standing overnight the filtrate yielded 2 g of 5-carboxy-2-oxindole as a yellow solid.. The crude dark brown product was dissolved in hot methanol, the insoluble material removed by filtration and the filtrate concentrated to give 5.6 g of 5-carboxy-2-oxindole as a brown solid.. The combined yield was 97%.

According to the analysis of related databases, 65435-04-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 193354-13-1, name is 5-Iodoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Iodoindolin-2-one

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 59-48-3

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 ML of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath.. solid N-iodosuccinimide (175 g) was added in portions over 10 minutes.. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid which had always present became very thick at this time.. The solid was collected by vacuum filtration, washed with 100 ML of 50 % acetic acid in water and then with 200 ML of water and sucked dry for 20 minutes in the funnel.. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

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; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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. COA of Formula: C8H8N2O

To ethyl acetate (10 mL) was added 6-aminoisoindolin-l-one (100 mg, 0.675 mmol), (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (179 mg, 0.675 mmol), and DCC (209 mg, 1.012 mmol). The reaction mixture was stirred for 24 h, diluted with ethyl acetate and filtered. The filtrate was washed with 10% citric acid (1 x 10 mL), brine and dried (MgSO4). The crude product was purified by silica gel chromatography (DCM and 0-10%MeOH as eluents) to afford a white foam (0.192 g). The foam was re-dissolved in DCM (5 mL) and to this solution was added TFA (2 mL). After 1 h, the reaction was concentrated to afford 129A (0.29 g, 105%) as a brown oil. LCMS m/z 296.3 [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 675109-45-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/157162; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 611-09-6, The chemical industry reduces the impact on the environment during synthesis 611-09-6, name is 5-Nitroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: Isatin 1 (3 mmol), 0.198 g malononitrile (3 mmol),0.420 g dimedone (3 mmol), and 0.025 g sodium acetate(0.3 mmol) were grinded with the pestle in mortar atambient temperature for 15 min. The resulting mixture wasair dried. Crude solid was then put on filter, rinsed withwater (2 9 2 cm3), and dried with water pump.

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-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elinson, Michail N.; Ryzhkov, Fedor V.; Zaimovskaya, Tatiana A.; Egorov, Mikhail P.; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 755 – 760;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Bromoisoindoline-1,3-dione

To a solution of hydroxyproline tripeptide precursor (200 mgs, 0.359mmol) in 4 mL of DMF at room temperature was added 4-bromophthalimide(97 mgs, 0.430 mmol) and triphenyl phosphine (206 mgs, 0.789 mmol).Sonicate until dissolved and add DIAD (152 uL, 0.789 mmol). Stir at roomtemperature overnight. Remove solvent under reduced pressure and extractwith ethyl acetate and water. ‘Separate the layers and dry over MgSCu, filterand strip. Purify using silica gel chromatography eluting (10 -100% ethylacetate in hexane). Further purify on reverse phase HPLC (ACN/Water) toafford 102 as a white solid (98 mgs, 36%). 1H NMR (300 MHz, CDCls): 5 7.95(s, 1H), 7.88 (d, J=7.9 Hz, 1H), 7.71 (d, J= 7.7 Hz, 1H), 7.65 (s, 1H), 7.43 (s, 1H),6.03 (m, 1H), 5.37 (d, J= 15.5 1H), 5.31-5.07 (bs, 5H), 4.91 (m, 1H), 4.77 (m, 1H),4.23-4.03 (bs, 7H), 3.81 (t, J= 7.9Hz, 1H), 2.75 (m, 2H), 2.01 (m, 1H), 1.68-1,50(bs, 8H), 1.30 (q, J= 7.0 Hz, 6H), 1.10 (s, 1H), 0.99 (s, 9H). 31P NMR (300 MHz,CDCls): 8 22.92 (s, IP), 22.75 (s, IP). LC/MS: 766 (M++ 1).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2006/20276; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 17702-83-9

General procedure: 0.91 g (3.6 mmol) N-(2 -bromoethyl) phthalimide was dissolved 20 mL DMF, added 0.53 g (3 mmol)1-benzylpiperazine, 0.62 g (4.5 mmol) K2CO3, heated to 60-70 °C reacted for 4 h, TLC detection, until the benzylpiperazinewas complete reaction. 30 mL of water was added, extracted three times withethyl acetate (20 mL× 3), the organic layer was extracted four times (30mL × 4)with saturated brine, dried with anhydrous magnesium sulfate, and the solventwas distilled off under reduced pressure, cooled to room temperature, silicagel column chromatography (100-200 mesh silica gel, eluent petroleum ether:ethyl acetate = 1:1 – 1: 4) to give 0.7 g (67percent yield) as a white solid. #10;

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 4b (1.00 g, 3.63 mmol) and 7b (1.11 g, 5.45 mmol) in THF (35 mL) was added NH4OAc (2.80 g, 36.3 mmol) in MeOH (35 mL). The reaction mixture was stirred at reflux temperature for 2 h and concentrated. The residue was diluted in CHCl3 and washed with a saturated aqueous solution of Na2CO3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 0-5% MeOH/CHCl3 to afford 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a yellow amorphous (1.14 g, 69%): 1H NMR (200 MHz, CDCl3, delta): 2.42 (d, J = 0.7 Hz, 3H), 3.22 (t, J = 6.8 Hz, 2H), 4.15 (t, J = 6.8 Hz, 2H), 6.00 (s, 2H), 6.69 (s, 1H), 6.85 (d, J = 8.1 Hz, 1H), 7.09 – 7.35 (m, 2H), 7.69 – 7.87 (m, 4 H); MS (ESI) m/z 459 [M+H]+, 35%, 481 [M+Na]+, 100%, 457 [M-H]-, 100%. To a suspension of 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione (1.12 g, 2.43 mmol) in EtOH (60 mL) was added hydrazine monohydrate (1.18 mL, 24.3 mmol). The reaction mixture was stirred at reflux temperature for 8 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated and the crude product was purified by column chromatography on NH-silica gel eluting with 2-7% MeOH/CHCl3 to afford 8b as a pale yellow amorphous (567 mg, 71%): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.9 Hz, 3 H), 2.91 (t, J = 5.9 Hz, 2 H), 3.18 (t, J = 5.9 Hz, 2 H), 6.00 (s, 2 H), 6.70 (d, J = 0.9 Hz, 1 H), 6.86 (d, J = 8.1 Hz, 1 H), 7.24 (dd J = 8.1, 1.7 Hz, 1 H), 7.36 (d, J = 1.7 Hz, 1 H); MS (ESI) m/z 329 [M+H]+, 90%, 351 [M+Na]+, 100%, 327 [M-H]-, 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanal, its application will become more common.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, Recommanded Product: 6-Chlorooxindole

To the mixture of 6-chloro-2-oxindole (16.2 g, 92 mmol) (Crescent) and 3-chloro-benzaldehyde (12.9 g, 92 mmol) (Aldrich) in methanol (109 mL) was added pyrrolidine (6.55 g, 92 mmol) (Aldrich) dropwise. The mixture was then heated at 70 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid (Yield 25.2 g, 95%).

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; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

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, 1-Acetylindolin-3-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem