Author: tianli

These common heterocyclic compound, 1127-59-9, name is 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. 1127-59-9

General procedure: Isatin 1 (3 mmol), malononitrile (0.2 g, 3 mmol,), bicyclic CH-acid 2 (3 mmol) and sodium acetate (0.025 g, 0.3 mmol) in ‘solvent-free’ manner or with additive (‘on-solvent’ manner) were grinded with a pestle and mortar at ambient temperature for 15 minutes. After the reaction was finished, the mixture was air-dried. Then the crude solid was put on filter, rinsed with water (2 mL) and EtOH (2 mL), and then dried with a water pump to isolate the spiro-oxindole 3.

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; Elinson, Michail N.; Vereshchagin, Anatoly N.; Ryzhkov, Fedor V.; Anisina, Yuliya E.; Arkivoc; vol. 2018; 4; (2018);,
Indoline – Wikipedia,
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3416-57-7, A common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, molecular formula is C11H9NO3, 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.

[0317] To a solution of 2-(2-oxopropyl)isoindoline-1,3-dione (1 g, 4.9 mmol) in 20 mL ofDMF-DMA was added some of 4A molecular sieve. The reaction mixture was stirred at 100 Cunder N2 for 15 hr. After cooling down toRT, the mixture was filtered and collected 600 mg(47.5%) of crude (E)-2-(4-(dimethylamino)-2-oxobut-3-enyl) isoindoline-1,3-dione as a solid.MS (ESI) m/e [M+It 259.1.

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GUO, Yunhang; BEIGENE, LTD.; WANG, Zhiwei; WO2014/173289; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, The chemical industry reduces the impact on the environment during synthesis 317-20-4, name is 7-Fluoroisatin, I believe this compound will play a more active role in future production and life.

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)+.

The chemical industry reduces the impact on the environment during synthesis 7-Fluoroisatin. I believe this compound will play a more active role in future production and life.

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

1055412-47-9, 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. 1055412-47-9, name is su-5614, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one (260 mg, 0.96 mmol), piperidine (95 muL, 0.96 mmol) and paraformaldehyde (43 mg, 1.44 mmol) in 5 mL of dioxane and 5 mL of EtOH was heated to 80 C. for 15 h. The resulting solution was cooled to room temperature followed by cooling to -20 C. for 1 h. The solid which formed was collected by filtration and rinsed with EtOH (previously cooled to -20 C.). The solid collected was dried under vacuum to give the title compound (180 mg, 51%) as a yellow-orange solid.

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; Allergan, Inc.; US2004/102509; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

39755-95-8, Name is 5-Methoxyisatin, 39755-95-8, 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.

5-Methoxyisatin (2.00 g, 11.2 mmol) was dissolved into 47% hydrobromic acid (20 mL) and refluxed at 150 C for 3 h. The solution was diluted with water (100 mL) and extracted by ethyl acetate (300 mL ¡Á 5). The organic layers were combined and dried with anhydrous sodium sulfate. After concentration in vacuo, the crude dark-brown solid (1.64 g, 89% yield) was obtained. In the subsequent synthesis, 5-hydroxyisatin was used without further purification. 1H NMR (CD3OD, 500MHz) delta 6.78 (d, 1H, J=8.3Hz, H-7), 6.94 (d, 1H, J=2.4Hz, H-4), 7.02 (dd, 1H, J=8.3, 2.4Hz, H-6).

Statistics shows that 5-Methoxyisatin is playing an increasingly important role. we look forward to future research findings about 39755-95-8.

Reference:
Article; Yasuda, Daisuke; Takahashi, Kyoko; Ohe, Tomoyuki; Nakamura, Shigeo; Mashino, Tadahiko; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7709 – 7714;,
Indoline – Wikipedia,
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99365-40-9, 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 99365-40-9 as follows.

n-Butyl lithium (2.5 M in hexanes, 3.8 mL, 9.5 mmol) was added dropwise over 30 minutes to a stirred suspension of 6-bromoindolin-2-one (preparation 1, 1.00 g, 4.7 mmol) and N,N,N’,N’-tetramethylethylenediamine (1.42 mL, 9.4 mmol) in tetrahydrofuran (20 mL) at – 78 C. The mixture was stirred for 1 hour, then 1,4-diiodobutane (3.11 mL, 23.6 mmol) was added dropwise over 5 minutes. The mixture was warmed to -20 C over a 1 hour period, was stirred for a further hour at this temperature and was then warmed to room temperature. After 3 hours stirring at room temperature, saturated aqueous ammonium chloride solution was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (10:1 hexanes/ethyl acetate) gave the title compound (0.57 g, 45%) as a pale pink solid. LRMS (m/z): 266/268 (M+1)+. 1H-NMR delta (CDCl3): 1.81-2.20 (m, 8H), 7.02-7.06 (m, 2H), 7.14-7.18 (m, 1H), 7.83 (brs, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 99365-40-9, and friends who are interested can also refer to it.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, molecular formula is C9H7NO3, 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. 118-29-6.

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 synthetic route of 2-(Hydroxymethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Zhongyan; Xu, Jiaxi; Tetrahedron; vol. 69; 3; (2013); p. 1050 – 1056;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3416-57-7, Adding a certain compound to certain chemical reactions, such as: 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-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 3416-57-7.

(1) Synthesis of N-[2-(N-methoxyimino)propyl]-phthalimide 1.33 g (6.55 mmol) of N-(2-oxopropyl)phthalimide was dissolved in 30 ml of ethanol and to the solution was added 1.64 g (19.7 mmol) of O-methylhydroxylamine hydrochloride. To this suspension was added 20 ml of 2N aqueous sodium hydroxide solution, followed by being stirred at room temperature for 12 hours. The reaction mixture was poured into 100 ml of water and extracted with chloroform (30 ml*3), and the combined organic layer was dried over magnesium sulfate. Chloroform was distilled off and the residual solids were washed with hexane to give 1.03 g (yield 68%) of the titled compound as colorless crystals. Melting point 114-131 C., 1 H-NMR spectrum (DMSO-d6, TMS as internal standard); delta=1.83(s, 3H), 3.73(s, 3H), 4.35(m, 2H), 7.82(s, 4H)ppm, IR spectrum (KBr); numax=2870w, 1680s, 1360s, 1315s, 1035s, 900w, 825m, 695m cm-1,

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, 2-(2-Oxopropyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsubishi Gas Chemical Co., Inc.; US5211738; (1993); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, This compound has unique chemical properties. The synthetic route is as follows.

A vial is charged with bis(l,5-cyclooctadiene)rhodium(I) tetrafluoroborate (0.054 g, 0.132 mmol, 0.10 eq.), l,4-bis(diphenylphosphino)butane (0.056 g, 0.132 mmol, 0.10 eq.), dry DCM (2mL) and sealed with a septum. The flask is evacuated and refilled with (3 times) and the reaction mixture is stirred under an atmosphere of . After 3h, volatiles are removed under a nitrogen stream. The residue is combined with Int 001 (0.397 g, 1.328 mmol, 1 eq.), 3-(l,3-dioxo-l,3-dihydroisoindol-2-yl)- propionaldehyde (0.406 g, 2.00 mmol, 1.5 equiv.) and 1,2-dichloroethane (2 mL) in a vial under a N2 atmosphere. The vial is sealed with a cap and heated at 100C. After 2 days, the mixture is concentrated in vacuo. The residue is purified by flash chromatography on silica gel (eluting with Heptane EtOAc 100/0 to 0/100, then DCM/MeOH 90/10) to afford Int 021. LCMS: MW (calcd): 502; m/z MW (obsd): 502-504 (M+H).

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; GALAPAGOS NV; LES LABORATOIRES SERVIER; BREBION, Franck, Laurent; ALVEY, Luke, Jonathan; AMANTINI, David; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene, Marie; PEIXOTO, Christophe; VARIN, Marie, Laurence, Claire; DE CEUNINCK, Frederic, Andre; POP-BOTEZ, Iuliana, Ecaterina; (317 pag.)WO2016/102347; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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. 1074-82-4

General procedure: The appropriate dibromoalkane derivative 2a-2e (11.9 mmol) was added slowly to a mixture of the starting material phthalimide potassium salt (1) (1g, 5.4 mmol) and anhydrous K2CO3 (0.82 g, 5.94 mmol) in acetone (15 mL). The reaction mixture was heated to 60-65 C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Water (50 mL) was added to the residue and the mixture was extracted with dichloromethane (30 mL ¡Á 3). The combined organic phases were washed with saturated aqueous NaCl, dried over Na2SO4, and filtered. The solvent was evaporated to dryness under reduced pressure. The crude product was purified on a silica gel chromatography using dichloromethane/acetone (50:1) as eluent to give the intermediates 3a-3e.

Statistics shows that 1074-82-4 is playing an increasingly important role. we look forward to future research findings about Potassium 1,3-dioxoisoindolin-2-ide.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem