Category: indolines-derivatives

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. 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

4-N-Ethylamino-N-methylphthalimide (5) A mixture of 10 g (0.057 mol) of 4-amino-N-methylphthalimide (4) [Flitsch, Chem. Ber. 94:2494(1961)], 17.5 g (0.11 mol) of diethyl sulfate, and 100 ml of 2,2,2-trifluoroethanol was refluxed for one day. The reaction mixture was cooled, concentrated under reduced pressure, and the residue partitioned between 250 ml of ethyl acetate and 100 ml of saturated sodium bicarbonate solution containing 10 ml of triethylamine. The ethyl acetate phase was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was recrystallized twice from acetone-hexane and then from aqueous methanol to give 3.4 g (29% yield) of the phthalimide (5) as fine yellow crystals, m.p. 157 C. Analysis: Calculated for C11 H12 N2 O2: C, 64.69; H, 5.92; N, 13.71. Found: C, 64.00; H, 5.71; N, 13.37. NMR Spectrum (C5 D5 N): delta 0.5 (t, J=7 Hz, 3H), 2.1 (s, 3H).

The synthetic route of 2307-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miles Laboratories, Inc.; US4261893; (1981); A;,
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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. 2058-74-4, name is 1-Methylisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H7NO2

General procedure: To an 8 mL dram vial was added iodobenzene diacetate (0.6 mmol, 1.5 equiv), arene (0.4 mmol,1 eq.), dichloroethane (2 mL), then 1 M hydrochloric acid (2 mL, 5 equiv). The solution wasallowed to stir (1000 rpm) at 50 C for the indicated amount of time. After which the solution waswashed with saturated sodium bicarbonate, followed by saturated sodium thiosulfate andconcentrated. The crude mixture was then purified by column chromatography.

The synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fosu, Stacy C.; Hambira, Chido M.; Chen, Andrew D.; Fuchs, James R.; Nagib, David A.; Chem; vol. 5; 2; (2019); p. 417 – 428;,
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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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H7NO3

To a solution of (1 ,3-dioxo-1 ,3-dihydro-isoindol-2-yl)-acetaldehyde (4.53 g) in EtOH (18 mL) was added a solution of 2-aminoethanthiol hydrochloride (2.9 g) in water (3.7 mL) followed by addition in one portion of potassium acetate (2.5 g). The reaction mixture was stirred at rt for 2 h and poured into a sat. NaHCO3 solution, the resulting precipitate was collected by filtration and washed with water and EtOH to yield the title compound as a white solid (4.92 g, 82percent).LC-MS: tR = 0.57 min; [M+H]+ = 248.95

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 2913-97-5.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; HAZEMANN, Julien; KOBERSTEIN, Ralf; SIEGRIST, Romain; SIFFERLEN, Thierry; WO2010/4507; (2010); A1;,
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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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H11NO3

To a stirred solution of acetic anhydride (5.0 mL, 53.0 mmol) and 7.7 wt % phosphorus pentoxide in methanesulfonic acid (Eaton’s Reagent) (5.0 mL, 4.60 mmol) was added 2-(3-oxobutyl)isoindoline-l ,3-dione (1.0 g, 4.60 mmol). The reaction was heated at 70 C and for 8 h. The reaction was allowed to cool to room temperature and maintained overnight. The reaction was diluted with EtOAc, washed with ice cold water, dried (Na2S04), filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (Analogix, SF40-115 g, 20 – 100% EtOAc in hexanes). The pure fractions were combined and evaporated to dryness and triturated with 10% EtOAc in hexanes, filtered and evaporated to dryness to give 2-((2,6-dimethyl-4-oxo-4H-pyran-3- yl)methyl)isoindoline-l,3-dione (290 mg, 1.024 mmol, 22.24 % yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 7.91 – 7.74 (m, 4 H), 6.06 (s, 1 H), 4.54 (s, 2 H), 2.43 (s, 3 H), 2.22 (s, 3 H). MS(ES) [M+H]+ 284.0.

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; DONATELLI, Carla, A.; WO2014/107277; (2014); A1;,
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550-44-7, name is 2-Methylisoindoline-1,3-dione, 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. Product Details of 550-44-7

(1) Refer to Figure 2 to determine the microchannel reactor connection mode, remove the preheating zone module, the channel type is cylindrical straight channel and circular microchannel structure, the number of microchannel mixed reaction modules is determined according to the flow rate and residence time.The N-methylphthalimide-concentrated sulfuric acid solution was regarded as the raw material A, the concentrated nitric acid solution was regarded as the raw material B, and the two materials were injected into the reaction zone through the metering pump at a flow rate of 10 ml/min and 25 ml/min, respectively. In the mixed residence reaction, the molar ratio of concentrated nitric acid to substrate is 1.2:1, the mass ratio of substrate to concentrated sulfuric acid is 1:2, and the microchannel reactor of Fig. 2 is used to control the temperature of 60 C, residence time. 180s, the reaction solution was quantitatively collected, washed with ice water, washed with water, filtered, and dried to obtain N-methyl-4-nitrophthalimide nitrated product, HPLC content analysis (normalized) 97%, yield 96 %.

The synthetic route of 550-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Wanfeng Chemical Co., Ltd.; Liu Tao; Yao Chenhua; Yu Xingying; Yu Xiaotian; (11 pag.)CN109305933; (2019); A;,
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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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3485-84-5

N- Vinyl phthalimide (0.100 g, 0.577 mol) was treated with 4N HCl/dioxane (0.433 mL, 1.73 mmol) at 25 C. After 3 hours the reaction mixture was concentrated under reduced pressure to provide an off white solid (112 g, 93% yield). 1H NMR (400 MHz, CDC13) delta 7.95-7.89 (m, 2H), 7.83-7.77 (m, 2H), 6.32 (q, J=6.8 Hz, 1H), 2.19 (d, J=6.8 Hz, 2H), LC tr=3.05 minutes (C-18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C).

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 3485-84-5.

Reference:
Patent; EUCLISES PHARMACEUTICALS, INC.; MARTINEZ, Eduardo, J.; TALLEY, John, J.; JEROME, Kevin, D.; BOEHM, Terri, L.; WO2014/12074; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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 20870-90-0, Quality Control of 5-Bromo-1-methyl-2-oxoindoline

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

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Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 21857-45-4

Weigh 5-methoxy indole (0.35 g, 2.35 mmol) in a two-necked flask,Add DCM (7mL) to dissolve,After adding DIPEA (0.36 g, 2.82 mmol) under ice bath conditions,Allyl chloride (0.23 g, 2.59 mmol) was added dropwise,After the addition is complete, the reaction is continued under ice bath conditions.Check the progress of the reaction through the TLC point plate,About 5 hours after the reaction is completed,After processing,DCM (20 mL) was added to dilute the reaction solution.Wash with saturated sodium bicarbonate solution (20 mL),Extract the sodium bicarbonate solution layer with DCM (10 mL×3).Dry with anhydrous magnesium sulfateconcentrate,Purification by column chromatographyThe target compound (0.28 g, yield 58.7%) was obtained.

The synthetic route of 21857-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Binjiang Pharmaceutical Research And Development Co., Ltd.; Tian Hongqi; Huang Gongchao; Cheng Ying; (48 pag.)CN107793413; (2018); A;,
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These common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-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. Formula: C8H6N2O3

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

The synthetic route of 5-Nitroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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Application of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-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.

Example 25: Synthesis of dimethyl-(6-phenylaminomethyl-phthalazin-l-yl)-amine; 5-Bromo-3-hydroxy-2,3-dihydro-isoindol-l-oneA mixture of zinc powder (8.68 g, 132.7 mmol), copper (II) sulfate pentahydrate(0.11 g, 0.44 mmol) and aqueous sodium hydroxide (135 mL, 2M solution) were cooled to 0 0C. Bromophthalimide (25 g, 110.6 mmol) was added in portions over 30 minutes, maintaining the temperature at 0 0C. The reaction was stirred at 0 0C for 30 minutes, and at room temperature for 3 h. The reaction was filtered, neutralized to pH 7 with concentrated HCl, diluted with EtOH, and then extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the desired compound (15.75 g, 63 %) as a colourless solid.

Statistics shows that 5-Bromoisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 6941-75-9.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
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