Category: indolines-derivatives

Career opportunities within science and technology are seeing unprecedented growth across the world, and those who study chemistry or another natural science at university now have increasingly better career prospects. Safety of 5-Methoxyindolin-2-one

General procedure: 3-(Propan-2-yliden)indolin-2-one (7a): A solution of indolin-2-one (500 mg, 3.76 mmol, 1.0 equiv.) in acetone (15 mL, 0.25 M) was heated in the presence of catalytic amounts of morpholine (164 mL, 164 mg, 1.88 mmol, 0.5 equiv.) for 16 h at reflux temperature. After complete consumption of the indolin-2-one (determined by thin layer chromatography (TLC)) all volatiles were removed under vacuum. Column chromatography(column diameter 5 cm, 30 g silica, v/v (P/EA)6 : 4-1 : 1) afforded the title compound (650 mg, 3.75 mmol, 99 %) as a yellow solid. Apparent multiplets which occur as a result of accidental equality of coupling constants to those of magnetically non-equivalent protons are marked as virtual (virt.). RF 0.70 (P/EA3 : 7; UV). deltaH (CDCl3, 250 MHz,300 K) 7.96 (1H, br s, NH), 7.52 (1H, br d, 3J 7.7, H-4), 7.19(1H, virt. td, 3JE3J 7.7, 4J 1.2, H-6), 7.01 (1H, virt. td, 3JE3J7.7, 4J 1.2, H-5), 6.85 (1H, ddd, 3J 7.7, 4J 1.2, 5J 0.6, H-7), 2.62(3H, s, H-30), 2.39 (3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K)169.5 (s, C-2), 155.7 (s, C-2′), 139.3 (s, C-7a), 127.7 (d, C-6),124.6 (s, C-3), 123.9 (d, C-5), 123.0 (s, C-3a), 121.8 (d, C-4),109.3 (d, C-7), 25.4 (q, C-1′), 23.3 (q, C-3′). The NMR data match the values reported in the literature.[9] 5-Methoxy-3-(propan-2-ylidene)indolin-2-one (7g): Prepared from 5-methoxy-2-oxindole according to RP 1 on a938 mmol scale. The title compound (176 mg, 866 mmol, 92 %) was obtained as a yellow solid. RF 0.45 (P/EA1 : 1; UV). numax(ATR)/cm1 3150w, 3030w, 2938w, 2836w, 1694vs (CO),1619s, 1594w, 1479s, 1305m, 1203w. deltaH (CDCl3, 250 MHz,300 K) 8.07 (1H, s, NH), 7.14 (1H, d, 4J 1.6, H-4), 6.78-6.72(2H, m, H-6/H-7), 3.81 (3H, s, OCH3), 2.62 (3H, s, H-3′), 2.36(3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K) 169.8 (s, C-2), 156.0(s, C-3′), 155.2 (s, C-5), 133.4 (s, C-7a), 125.6 (s, C-3a), 123.4 (s,C-3), 111.9 (d, C-4), 111.8 (d, C-6), 109.3 (d, C-7), 56.1 (q,OCH3), 25.3 (q, C-1′), 23.3 (q, C-30). m/z (HRMS ESI)204.1019; [M H)](C12H13NO2) requires 204.1019.

Future efforts will undeniably focus on the diversification of the new catalytic transformations. These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. Keep reading other articles of 7699-18-5.

Reference:
Article; Maturi, Mark M.; Poethig, Alexander; Bach, Thorsten; Australian Journal of Chemistry; vol. 68; 11; (2015); p. 1682 – 1692;,
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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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C22H19N3O6

210.7 g (0.5 mol) of (S)-2-{[2-oxo-3-(4-(3-oxomorpholine)phenyl]oxazolidine-5-yl] prepared in Example 7 was added to the reaction flask. Methyl isonon-1,3-dione (formula VII), 1500 ml of anhydrous ethanol, and 500 ml of a 30% aqueous solution of methylamine were stirred well.The reaction was heated to 40C to 60C for 8 hours, and TLC control (dichloromethane:methanol = 20:1, volume ratio) was completed.Adjust pH to 1-2 with 10% hydrochloric acid.A large amount of white solids precipitated and cooled to about 15C.Stir for 2 hours, filter and filter cake washed with 300 ml absolute ethanol.Drying under reduced pressure gave 147.0 g of a white solid (formula VIII) in a molar yield of 89.7%. The HPLC purity was 98.7%.

Keep reading other articles of (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione! 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; Peking University Fangzheng Group Co., Ltd.; Peking University Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Xu Hong; Tian Juan; Zhang Zheng; Wang Wei; Ren Juan; (16 pag.)CN105085508; (2017); B;,
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Application In Synthesis of 6-Nitroisoindolin-1-one, The prevalence of solvent effects in heterogeneous catalysis has motivated developing quantitative kinetic, spectroscopic, and theoretical assessments of solvent structures and their interactions with reaction intermediates and transition states.

5-Amino-2,3-dihydroisoindol-l-oneH2N; [693] Iron powder (158mg, 2.83mmol), water (61uL), and HC1 (37percent, 5uL,0.566mmol) were added into the suspension of 5-nitro-2,3-dihydroisoindol-l-one (50.4mg,0.283mmol) in EtOH (754|^L). The above mixture was heated at 95°C for 2h. After thattime, several drops of 7N NH3 in MeOH were added to basify the solution, and the solid wasfiltered off. The filtrate was concentrated in vacua to obtain a light-yellow solid that waspurified by preparative TLC eluting with 10percent MeOH/CH2Cl2 to give a light-yellow solid of5-amino-2,3-dihydroisoindol-l-one. ‘HNMR (CD3OD, 400 MHz): 5 = 7.48 (s, 1 H), 8.08 (s,2 H), 9.91 (s, 1 H), 10.66 (d, 1 H, J= 8.8 Hz). MS (ES+): m/z 149.21 (100) [MH1″]. HPLC: *R= 1.20 min (ZQ2000, polar_5 min).

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; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
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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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Potassium 1,3-dioxoisoindolin-2-ide

a) Preparation of 5-bromopentylphthalimide Potassium phthalimide (5.4 mmoles) was added to a solution of 1,5-dibromopentane (3.72 g; 16.2 mmoles) in dimethylformamide (8 ml) and heated to 80C approx. under stirring. After 2 hours, water was added and the solution was repeatedly extracted with ether. The collected organic phases were washed with water, dried on Na2SO4 and evaporated under reduced pressure to give a solid (4.50 g), which was purified by chromatography on silica gel (Etp/Et2O 8:2) yielding 2.38 g of a white solid. Yield 68%.

Keep reading other articles of Potassium 1,3-dioxoisoindolin-2-ide! 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; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
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Career opportunities within science and technology are seeing unprecedented growth across the world, and those who study chemistry or another natural science at university now have increasingly better career prospects. Recommanded Product: 7-Chloroisatin

General procedure: To a stirred mixture of isatins (1mmol) and malononitrile/ethyl cyanoacetate (1mmol) in methanol (3ml), was added piperidine (10molpercent) and the reaction mixture was stirred at room temperature for 10min. Then 5,7-dihydroxy-4-methyl-2H-chromen-2-one (1mmol) was added to it. The resulting mixture was stirred at reflux until the reaction was completed as indicated by TLC. The resulting precipitate was treated with dilute HCl and washed with water to afford the pure product for analysis.

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Reference:
Article; Pal, Suman; Khan, Md. Nasim; Karamthulla, Shaik; Choudhury, Lokman H.; Tetrahedron Letters; vol. 56; 2; (2015); p. 359 – 364;,
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category: indolines-derivatives,Chemistry involves the study of all things chemical – chemical processes, chemical compositions and chemical manipulation – in order to better understand the way in which materials are structured, how they change and how they react in certain situations.

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

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:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
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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 2436-29-5 as follows. 2436-29-5

Step 5. 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione To a solution of 1-(3-benzylquinolin-2-yl)-2-methylpropan-1-amine 15 (31 mg, 1 eq.) in CH2Cl2 (3 ml), was added aldehyde 16 (0.8 eq., 17 mg), sodium triacetoxy borohydride, and acetic acid. The reaction mixture was stirred for 3 h at room temperature. Water was added and then the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to yield 46 mg of 2-(3-{[1-(3-benzylquinolin-2-yl)-2-methylpropyl]amino}propyl)-1H-isoindole-1,3(2H)-dione 17.

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Reference:
Patent; Wang, Weibo; Constantine, Ryan N.; Lagniton, Liana Marie; Bair, Kenneth; US2005/261337; (2005); A1;,
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These common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-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. 883-44-3

4-hydroxycoumarin (6.17 mmol, 1.0 g), PPh3 (6.48 mmol, 1.70 g), and 2-(3-hydroxy-propyl)-isoindole-1,3-dione (6.48 mmol, 1.33 g) is disolved in 20 mL THF and is cooled to 0 C. DIAD (6.79 mmol, 1.33 mL) is added dropwise at 0 C. A precipitate is formed immediately and the reaction mixture thickens. The precipitate is filtered, is washed with Et2O and is dried to afford the title compound (1.62 g, 75%). 1H NMR (DMSO-d6, 300 MHz) delta 7.82 (4H, m), 7.61 (2H, m), 7.37 (1H, m), 7.21 (1H, m), 5.83 (1H, s), 4.28 (2H, t, J=5.75 Hz), 3.83 (2H, t, J=6.25 Hz), 2.19 (2H, m); MS (ESI, Pos.) calcd for C20H15NO5 m/z [M+H]=350.1, found 350.1.

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

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/54681; (2005); A1;,
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We’ll be discussing some of the latest developments in chemical about CAS: 2436-29-5. 2436-29-5

Intermediate 62 : 2-f3-f4-Methyl-3-oxopiperazin-l-vnpropynisoindoline-l,3- dione (0595) To a mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (515 mg, 2.53 mmol, commercially available from Fluorochem) and Na(OAc)3BH (815.9 mg, 3.85 mmol) in 2-MeTHF (20 mL) was added l-methylpiperazin-2-one (0.420 mL, 3.82 mmol, commercially available from Fluorochem). The mixture was stirred at rt for 4 h 45 min. To the reaction mixture was added aqueous 2M Na2C03 (10 mL) and this mixture stirred at rt for 10 min giving an aqueous phase at approximately pH 10. The layers were separated and the aqueous layer washed with EtOAc (2 x 10 mL). The organic layers were filtered through a cartridge fitted with a hydrophobic frit and the filtrate evaporated in vacuo to give a pale yellow crystalline solid. 2-(3-(4-methyl-3-oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (660.5 mg, 2.192 mmol, 86 % yield). (0596) LCMS (2 min high pH); Rt = 0.74 min, m/z = 302 for [MH]+

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Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); A1;,
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These common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-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. Recommanded Product: 6-Bromo-7-fluoroindoline-2,3-dione

To a solution of 6-bromo-7-fluoroindoline-2,3-dione (1.41 g, 5.80 mmol) in 2 N NaOH (15 mL) was added H202 (30%, 3 mL) at 0C, the mixture was stirred at 0C for 30 mm. After stirring at rt for 16 h, the mixture was poured into ice water, the solution was acidified with Conc. HC1, the precipitate was filtered and dried in the air to afford the desired product as a white solid (1.2 g, 89% yield)

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; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (246 pag.)WO2017/87528; (2017); A1;,
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