Indolines-derivatives

Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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. Product Details of 19727-83-4

10.0 g (0.061 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 100 ml of dimethylformamide in a synthetic nitrogen atmosphere, stirred for about 10 minutes at room temperature,12.6 g (0.068 mol) of (1-bromoethyl) benzene and 12.4 ml (0.073 mol) of diisopropylethylamine (DIPEA) were added to the reaction solution. The reaction solution was gradually heated and stirred at 100 C for 5 hours, Completed.After cooling the reaction mixture to room temperature, 100 ml of distilled water and 200 ml of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was separated and washed with H 2 O. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure The obtained solid product was dispersed in 50 ml of methanol, stirred for 30 minutes, filtered and dried to obtain 12.5 g of 6-nitro-2,3-dihydro-1- (1-phenylethyl)-1H-indole (76.7%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
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Application of 320734-35-8,Some common heterocyclic compound, 320734-35-8, name is 7-Bromooxindole, molecular formula is C8H6BrNO, 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 2a-j (1.50 mmol) and 5 (1.50 mmol) in ethanol (10 mL) was treated with a catalytic amount of piperidine. The reaction mixture was stirred under reflux until complete consumption of the substituted indolin-2-ones was observed by TLC. After cooling, the precipitate was filtered, recrystallised from absolute ethanol and dried in air to furnish pure (E)-3-(benzothiazol-2-ylmethylene)indolin-2-ones 6a-j.

The synthetic route of 320734-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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Related Products of 611-09-6, These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-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.

General procedure: 30 mg of SiO2_g-C3N4 nanocomposite was dispersed in aqueous media (3 ml) for 30 min and dimedone or 4-hydroxycoumarin (1 mmol), malononitrile (1 mmol) and isatin (1.0 mmol) were added to the mixture. Then, the mixture was stirred at reflux conditions for an appropriate time, while the reaction progress was monitored by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was employed for the extraction of crude product and the products were dried over anhydrous Na2SO4. The solvent was evaporated followed by recrystallizing of the crude product in hot ethanol, and pure products were identified by IR, 1H and 13C NMR spectral data. The SiO2_g-C3N4 nanocatalyst was washed with EtOH, dried and reused for the next run.

Statistics shows that 5-Nitroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 611-09-6.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri, Mohammad Ali; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 1173 – 1188;,
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Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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. Safety of 2,3-Dioxoindoline-5-sulfonyl chloride

A solution of rpml21 (0.211 g, 0.861 mmol) and morpholine (0.187 g, 2.139 mmol, 2.5 eq), in anhydrous DCM (7 ml) and anhydrous chloroform (1 ml) was stirred for 3h at room temperature under Ar. The yellow precipitate was collected by filtration and dried under vacuum. The crude product was used in the next step 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 132898-96-5, its application will become more common.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; WO2007/117699; (2007); A2;,
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24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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. Recommanded Product: N-(6-Bromohexyl)phthalimide

2-[6-(4-phenyl-1-piperidinyl)hexyl]-1H-isoindole-1,3(2H)-dione: To the 500 ml RB-flask was added 4-phenylpiperidine hydrochloride (5 g, 25 mmol), N-(6-bromohexyl)phthalimide (15.5 g, 50 mmol), N,N-diisopropylethylamine (21.8 ml, 125 mmol), tetrabutylammonium iodide (0.2 g), and dioxane (250 ml) at room temperature. The reaction mixture was stirred at 100 oC for 72 h. The solvent was removed in vacuo and the crude product was purified by flash chromatography (98:2=Chloroform: 2N ammonia in methanol) to afford 7.67 g of the desired product (77% yield): 1H NMR (400 MHz, CDCl3) delta 7.78-7.79 (m, 2H), 7.74-7.65 (m, 2H), 7.32-7.14 (m, 5H), 3.69 (t, 2H, J=7.35 Hz), 3.06 (d, 2H, J=11.0 Hz), 2.49 (quintet, 1H, J=7.6 Hz), 2.36 (t, 2H, J=7.6 Hz), 2.02 (t, 2H, J=12.5 Hz), 1.82 (br s, 4H), 1.69 (t, 2H, J=6.3 Hz), 1.54 (br s, 2H), 1.37 (br s, 4H); ESMS m/e: 391.3 (M+H) +; Anal. Calc. for C25H30N2O2+0.2H2O: C, 76.19; H, 7.77; N, 7.11. Found: C, 76.14; H, 7.38; N, 7.13.

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Borowsky, Beth; Blackburn, Thomas P.; Ogozalek, Kristine; US2003/82623; (2003); A1;,
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Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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. category: indolines-derivatives

Step 2 5-Amino-1,3-dihydro-indol-2-one 5-Nitro-1,3-dihydro-indol-2-one 30b (3.56 g, 20 mmol) was dissolved in 200 ml of acetic acid under stirring, and added with palladium on activated carbon (1.0 g, 5%) to the solution at room temperature. The reaction mixture was stirred under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, and concentrated under reduced pressure to obtain the title compound 5-amino-1,3-dihydro-indol-2-one 30c (2.04 g, yield 68.9%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-79-5, its application will become more common.

Reference:
Patent; ChoTang, Peng Cho; Su, Yidong; Li, Yali; Zhang, Lei; Zhao, Fuqiang; Yang, Jialiang; Zhou, Ying; Bie, Pingyan; Qian, Guangtao; Ju, Minggang; US2010/75952; (2010); A1;,
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Reference of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-1-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.

Intermediate 2B:; [00193] Potassium nitrate (1.215 g, 12.02 mmol) was added portionwise to a solution of Intermediate 2A (1.6 g, 12.02 mmol) in sulfuric acid (24 mL) at 0 0C over 10 min. The reaction mixture was stirred for 3 h at ambient temperature. The reaction mixture was poured onto ice and the resulting precipitate was washed with water and dried in vacuo to yield Intermediate 2B (1.85 g, 10.38 mmol, 86 % yield) as a beige solid.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
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Electric Literature of 3416-57-7, 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

2-((4-Methyl-2.5-dioxoimidazolidin-4-yl)methylcarbamoyl)benzoic acid [0180] Phthalimido acetone (27-1) (14.2 g, 70 mmol, 1 eq.), ammonium carbonate (23.5 g, 245 mmol, 3.5 eq), potassium cyanide (6.8 g, 105 mmol, 1.5 eq.) in EtOH (70 mL) and H2O (70 niL) were heated at 75 0C for 18 h in a sealed tube. The reaction mixture was cooled to room temperature and the volatiles were evaporated in vacuo. The reaction mixture was partitioned between ethyl acetate (150 mL) and H2O (100 mL). The aqueous phase was adjusted to pH 4 and extracted with more ethyl acetate (2 x 150 mL). Organic layers were combined, dried (MgStheta4) and concentrated in vacuo to yield the crude product (27-2), which was directly used in the next step. Yield: 12.33 g (61%). 1H-NMR (400 MHz, CD3OD^) delta 7.60-7.41 (m, 4H), 3.70 (d, IH), 3.56 (d, IH), 1.44 (s, 3H). LCMS – [M+H] m/z 292.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Oxopropyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVABAY PHARMACEUTICALS, INC.; JAIN, Rakesh, K.; LOW, Eddy; FRANCAVILLA, Charles; SHIAU, Timothy P.; KIM, Bum; NAIR, Satheesh, K.; WO2010/54009; (2010); A1;,
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Synthetic Route of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: To a mixture of isatin (1 equiv.) and phenyl acetylene (1.2 equiv.) in water (3 mL), CuWO4 (10 mol%) and DABCO (40 mol%) were added at room temperature and the mixture was heated at 60 C for 2 to 5 h. After completion of reaction (monitoring by TLC) mixture was cooled to room temperature and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography to give 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
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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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 104618-31-7

To a solution of 1.534 g (6.26 mmol) of 2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione in 60 mL THF was added 0.553 g (13.8) NaH (60% in oil) and reaction mixture stirred under N2 until gas formation ceased. The mixture was cooled to 0 C. and 3.56 g (25.1 mmol) MeI was added and the reaction was stirred at 25 C. for 24 hours. The mixture was then poured into 180 mL sat. NH4Cl(aq) and extracted 3 times with DCM. The organic layers were dried over Na2SO4, concentrated and then purified via chromatography (50% EtOAc/Hex) to give 908 mg of 2-(4-Methoxy-cyclohexyl)-isoindole-1,3-dione (48.3% yield, LCMS (m/z): M+H=301.1). That was dissolved in 40 mL EtOH and 324 mg (8.76 mmol) Hydrazine was added. The reaction mixture was stirred at 65 C. for 3 hours. By the end of the 3 hours the solution was mostly white solid and a little liquid. The reaction was filtered and washed 3 times with 30 mL MeOH and concentrated to give 450 mg of crude product of 4-Methoxy-cyclohexylamine (ca. 100% yield). LCMS (m/z): M+H=130.2.

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 104618-31-7.

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
Indoline – Wikipedia,
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