Category: indolines-derivatives

317-20-4,You could be based in a pharmaceutical company, working on developing and trialing new drugs; or in a public-sector research center, helping to ensure national healthcare provision keeps pace with new discoveries.

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)+.

Keep reading other articles of 7-Fluoroisatin! Don’t worry, you don’t need a PhD in chemistry to understand the explanations! 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

Electric Literature of 118289-55-7, The chemical industry reduces the impact on the environment during synthesis 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

Statistics shows that 6-Chloro-5-(2-chloroethyl)indolin-2-one is playing an increasingly important role. we look forward to future research findings about 118289-55-7.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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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. 6344-05-4, name is 4-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 6344-05-4

80 kg of 2- [4- (1,3-dioxo-2-isoindolinol] phenylbutyric acid prepared in the method of Example 1 and 480 L of acetic acid were charged into a reaction vessel, and stirring was started. A mixture of 64 kg Zinc powder into the reaction tank, atmospheric pressure into the hydrogen chloride gas,The reaction temperature was controlled at 82 C, the reaction started, the reaction time was 1 hour, the reaction liquid all clear. Filter, wash the residue with acetic acid, The filtrate and washings were combined, the solvent was removed under reduced pressure, the residue was poured into appropriate amount of water, stirred and adjusted to pH 5.5-6.5 by ammonia water, dried and centrifuged to give 72.3 kg of indobufen crude product with a yield of 94.7% and a purity of 98.0%

The potential utility of systematic synthetic strategy will be applicable to efficient generations of chemical libraries of compounds to find ‘hit’ molecules.Read on for other articles about 6344-05-4.

Reference:
Patent; Hangzhou China-USA East China Pharmaceutical Co., Ltd.; Cao Dongsheng; Han Tao; Zhou Hanjun; Yu Rui; (8 pag.)CN106631974; (2017); A;,
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Electric Literature of 480-91-1,When developing chemical systems it’s of course important to gain a deep understanding of the chemical reaction process.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

Hope you enjoy the show about 480-91-1.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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Related Products of 3339-73-9, 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 3339-73-9 as follows.

General procedure: 1.0 mmol of (1,3-dioxoisoindolin-2-yl) acid, N-ethyl-N-dimethylaminopropylcarbodiimide (EDC) (1.1 mmol), hydroxybenzotriazole(HOBt) (1.2 mmol) and N,N-Diisopropylethylamine (2.0 mmol) weremixed in minimum DMF and the obtained mixture was stirred for5 min. Then, 4-aminoquinoline-diamines (1.0 mmol) was added to thereaction mixture and the stirring was continued for 5 h. The reactionend was proved by thin layer chromatography (TLC). Then, DMF wasevaporated using rotary evaporator and cold water (20 mL) was added,and solid precipitates obtained were filtered and washed with coldwater. The crude product was recrystallized in absolute ethanol.

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Reference:
Article; Rani, Anu; Legac, Jenny; Rosenthal, Philip J.; Kumar, Vipan; Bioorganic Chemistry; vol. 88; (2019);,
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These common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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. Synthetic Route of 2058-74-4

General procedure: The dicationic ionic liquid 10 (27.03 mg, 10 mol %), was added to a mixture of 1,3-dicarbonyl (1 mmol), isatin (1 mmol), malononitrile (1 mmol), and K2CO3 (13.8 mg, 10 mol %) in water (3 mL). The reaction mixture was stirred at reflux for the appropriate time. After reaction completion (TLC), the reaction mixture was cooled to room temperature and filtered. The filtrate was washed with cool ethanol (3 × 5 mL) to obtain the corresponding 4H-pyran. The crude products were purified by recrystallization from ethanol (95%). To recover 10, the ethanol/water phase was evaporated under reduced pressure and the crude was washed with ethyl acetate (3 × 5 mL) and air dried.

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-Methylisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Niknam, Khodabakhsh; Khataminejad, Mohsen; Zeyaei, Fariba; Tetrahedron Letters; vol. 57; 3; (2016); p. 361 – 365;,
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HPLC of Formula: C8H6ClNO, The chemical industry reduces the impact on the environment during synthesis 17630-75-0, name is 5-Chloro-2-oxindole, I believe this compound will play a more active role in future production and life.

7-Bromo-5-Chloro-2-Oxindole 5-Chloro-2-oxindole (16.8 g) and 19.6 g of N-bromosuccinimide were suspended in 140 mL of acetonitrile and refluxed for 3 hours. Thin layer chromatography (silica, ethyl acetate) at 2 hours of reflux showed 5-chloro-2-oxindole or N-bromosuccinimide (Rf 0.8), product (Rf 0.85) and a second product (Rf 0.9) whose proportions did not change after another hour of reflux. The mixture was cooled to 10 C., the precipitate was collected by vacuum filtration, washed with 25 mL of ethanol and sucked dry for 20 minutes in the funnel to give 14.1 g of wet product (56% yield). The solid was suspended in 200 mL of denatured ethanol and slurry-washed by stirring and refluxing for 10 minutes. The mixture was cooled in an ice bath to 10 C. The solid product was collected by vacuum filtration, washed with 25 mL of ethanol and dried under vacuum at 40 C. to give 12.7 g (51% yield) of 7-bromo-5-chloro-2-oxindole.

In the meantime we’ve collected together some recent articles in this area about 17630-75-0 to whet your appetite. Happy reading!

Reference:
Patent; Sugen. Inc.; US2003/100555; (2003); A1;,
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Electric Literature of 17564-64-6, Researchers are common within chemical engineering and are often tasked with creating and developing new chemical techniques, frequently combining other advanced and emerging scientific areas.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.55 2-((2-(2-(Pentan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (3C) White powder, mp 125-126 C, 84% yield; 1H NMR (400 MHz, CDCl3): delta 0.92-0.95 (t, 3H, CH3), 1.59-1.61 (m, 2H, CH2), 1.93 (s, 3H, CH3), 2.23-2.27 (t, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.75-7.76 (m, 2H, Ar), 7.86-7.87 (m, 2H, Ar). 13C NMR (100 MHz, CDCl3): delta 13.8, 14.0, 17.5, 19.6, 19.8, 22.9, 32.2, 34.1, 40.6, 45.0, 45.1, 123.6, 131.7, 134.3, 158.0, 166.7, 170.0, 171.1.

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

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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With the volume and accessibility of scientific research increasing across the world, it has never been more important to continue building the reputation for quality and ethical publishing we’ve spent the past two centuries establishing., Application In Synthesis of 2-Allylisoindoline-1,3-dione

General procedure: A magnetically stirred solution of N-allylphthalimide 4 (1 equiv) and a xanthate 3 (2-4 equiv) in 1,2-dichloroethane (2-4 mL/mmol of N-allylphthalimide) was heated at reflux for 15 min. DLP (3-5 mol percent) was added and additional DLP (5 mol percent) was added per hour until complete consumption of 4. The mixture was allowed to cool to room temperature and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel to yield the desired product 5.#10;

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

Reference:
Article; Kakaei, Saeed; Chen, Ning; Xu, Jiaxi; Tetrahedron; vol. 69; 1; (2013); p. 302 – 309;,
Indoline – Wikipedia,
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COA of Formula: C10H9NO3,You could be based in a pharmaceutical company, working on developing and trialing new drugs; or in a public-sector research center, helping to ensure national healthcare provision keeps pace with new discoveries.

Sodium hydroxide solution (1N, 20 ml) was added to a solution of methyl 2-oxoindoline-6-carboxylate (2 g, 10.46 mmol, 1.00 equiv) in methanol (20 ml). The resulting solution was stirred for 2 hours at 80 C. The reaction mixture was cooled to 30 C., diluted with 50 ml of H2O and extracted with 2*30 mL of dichloromethane. The aqueous layers were combined and the pH adjusted to 2 with aqueous hydrochloric acid (6 N). The solids were collected by filtration and dried to give the title product 1.28 g (69%) as a brown solid. 1H NMR (400 MHz, CDCl3) delta: 12.86 (s, 1H), 10.50 (s, 1H), 7.55 (m, 1H), 7.32-7.30 (m, 2H), 3.56 (s, 2H).

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); A1;,
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