Tag: M.W=100-200

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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Nitroindolin-2-one

5-Nitro-1,3-dihydro-indol-2-one (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of 5-amino-1,3-dihydro-indol-2-one as a white solid.

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 20870-79-5.

Reference:
Patent; Sugen, Inc.; US6846839; (2005); B1;,
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Reference of 2058-74-4, 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.

General procedure: Sulfonated-b-cyclodextrin (b-CD-SO3H) (0.1 mmol) was dissolved in water(2 mL) at room temperature by stirring to get the clear solution. Then thereaction was shifted to reflux with addition of isatin (1 mmol) and indole(2 mmol) with constant stirring. The progress of the reaction was monitored byTLC. After completion of reaction, it was cooled to room temperature andfiltered, to get the solid. The crude product was recrystallized from aqueousethanol (60:40) giving pure 3,3-di(indolyl)indolin-2-ones.

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

Reference:
Article; Tayade, Yogesh A.; Patil, Dipak R.; Wagh, Yogesh B.; Jangle, Asha D.; Dalal, Dipak S.; Tetrahedron Letters; vol. 56; 5; (2015); p. 666 – 673;,
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Application of 118-29-6, 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. 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 2,3,3-Trimethylindolenine (1) (2.0 g, 12.5 mmol, 1.1 eq.) and A (Hydroxymethyl)phthalimide (3) (2.02 g 11.4 mmol, 1 eq.) were added 14.7 mL of concentrated sulfuric acid and the system stirred at room temperature for 6 days. The reaction was then poured over ice and made basic with concentrated aqueous ammonium hydroxide. After crystallizing at -20 C overnight, the resulting precipitate was filtered, rinsed with ice cold water, and dried under vacuum to give indolenine 4 as a light yellow shiny crystalline solid. Yield 88.3%. XH NMR (400 MHz, CDCl3); d 7.82-7.87 (m, 2H, Ar- H); 7.67-7.72 (m, 2H, Ar-H); 7.44-7.48 (m, 1H, Ar-H); 7.35-7.42 (m, 2H, Ar-H); 4.87 (s, 2H,CH2); 2.25 (s, 3H, CH3) 1.28 (s, 6H, CH3).

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; SIMBERG, Dmitri; SMITH, Weston J.; (107 pag.)WO2019/126565; (2019); A1;,
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Electric Literature of 603-62-3, These common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, 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.

In a 2500 mL round bottom flask containing 0.52 mol (100 g) of 3-nitrophthalimide, Add anhydrous ethanol 800mL, Under stirring, 385 mL of a methanolic solution of KOH at a concentration of 80 g ¡¤ L -1 (1 h addition, 0.55 mol KOH) was added dropwise and stirring continued for 3 h at room temperature, filter, The resulting white solid was rinsed with absolute ethanol, drying, The quality of 119g.

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Agricultural Sciences Plant Protection Institute; Mei Xiangdong; Si Weijie; Zhang Tao; Ning Jun; (17 pag.)CN104447498; (2017); B;,
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Synthetic Route of 32692-19-6, A common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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.

A solution of 5-nitroindoline (6) (0.5 g, 3.05 mmol) in DMF (10 mL) was treated with NaH (0.39 g, 9.75 mmol, 60% wt in mineral oil) at 0 C resulting in an orange mixture. ;The reaction mixture was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (0.87 g, 6.09 mmol) resulting in a dark red mixture. ;The reaction was heated to 90 C and stirred for 1.5 h. ;After allowing the reaction to cool to room temperature, water was added and the product was extracted into EtOAc. ;The combined ethyl acetate layer was washed with water, brine and dried (Na2SO4). ;Solvent was evaporated and the crude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain the title compound (0.4 g, 56%) as a solid. 1H NMR (DMSO-d6) delta 7.96 (dd, 1H, J = 2.1, 8.7 Hz), 7.79 (d, 1H, J = 2.1 Hz), 6.49 (d, 1H, J = 9.0 Hz), 3.72 (t, 2H, J = 8.7 Hz), 3.39 (t, 2H, J = 6.6 Hz), 3.04 (t, 2H, J = 8.7 Hz), 2.44 (t, 2H, J = 6.3 Hz), 2.18 (s, 6H).

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
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Electric Literature of 16078-34-5,Some common heterocyclic compound, 16078-34-5, name is 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, molecular formula is C10H11NO, 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.

Step I:Methanesulfonyl chloride was added dropwise to a stirred solution of 1-(indolin-5-yl)ethanone and 5 mL of pyridine under N2. The reaction was stirred at room temperature overnight. When complete as determined by HPLC using the protocol described in Example 2 above, as well as by TLC (8/2 PE/EtOAc), the solvent was evaporated, the evaporation residue was dissolved in 50 mL ethyl acetate, washed with 100 mL cold 0.5M HCl and then with brine and finally dried on Na2SO4. The solvent was evaporated and the product was used in the next step without further purification (400 mg, yield 38%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, its application will become more common.

Reference:
Patent; Dynamix Pharmaceuticals LTD.; US2012/302609; (2012); A1;,
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Reference of 14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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.

A stirred solution of methyl 2-oxoindoline-6-carboxylate (D1) (2.0 g, 10.47 mmol) in acetic anhydride (16 ml) was heated to 130 C under inert atmosphere for 6 h. After complete consumption of the starting material (monitored by TLC), the reaction mixture was cooled to approximately 21 C. The precipitate was filtered, washed with n-hexane (2 x 50 ml) and dried in vacuo to afford compound D2 as a yellow solid (1.5 g, 61.5%).1H NMR (400 MHz, DMSO -de)6 8.66 (s, 1 H), 7.82 (d, J = 8.0 Hz, 1 H), 7.48 (d, J = 8.0 Hz, 1 H), 3.91 (s, 2H), 3.87 (s, 3H), 2.57 (s, 3H)

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

Reference:
Patent; SYNTHIS, LLC; THOMAS-KARYAT, Dori A.; (0 pag.)WO2020/13803; (2020); A1;,
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Application of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

This compound was obtained by mixing fuming nitric acid (1.0 mmol) and the precursor compound (0.10 mmol) at – 5 C and stirring for 2 h (Scheme 1). The reaction mixture was poured into a mixture of water and ice. The pH was adjusted to 6 by adding CaCO3. The obtained white solid was vacuum filtered, with yield 93%; Mp 87.1-89.5 C. IR (ATR): 3062, 3030, 2978, 2886, 1774, 1716, 1608, 1422, 1402, 1288, 982, 870, 722, 530. 1H NMR (200 MHz, DMSO-d6): 3.95 (t, 2H), 4.71 (t, 2H), 7.86 (br s,4H). 13C NMR (50 MHz, DMSO-d6): 34.8, 70.8, 123.1, 131.4, 134.4, 167.5. Anal. Calcd. for C10H8N2O5. Calcd. (%): C, 50.85; H, 3.41; N, 11.86. Found (%): C, 51.09; H, 3.32; N, 11.77.

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Godin, Adriana M.; Araujo, Debora P.; Menezes, Raquel R.; Brito, Ana Mercy S.; Melo, Ivo S.F.; Coura, Giovanna M.E.; Soares, Darly G.; Bastos, Leandro F.S.; Amaral, Flavio A.; Ribeiro, Lucas S.; Boff, Daiane; Santos, Julliana R.A.; Santos, Daniel A.; Teixeira, Mauro M.; De Fatima, Angelo; Machado, Renes R.; Coelho, Marcio M.; Pharmacology, Biochemistry and Behavior; vol. 122; (2014); p. 291 – 298;,
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These common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, 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: C8H4N2O4

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

The synthetic route of 3-Nitrophthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
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Synthetic Route of 3676-85-5, 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 3676-85-5 as follows.

Example 82 N-(2-Chlorobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (165 mg, 0.60 mmol, 1.2 eq) and triethylamine (61 mg, 0.60 mmol, 1.2 eq) were added to a solution of 2-chlorophenylacetic acid (85 mg, 0.50 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (81 mg, 0.50 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate to give the title compound as a crystal (37 mg, 22.6%). MS m/z: 329 1H-NMR delta: 4.40 (2H, d, J = 5.61 Hz), 6.94 (1H, t, J = 5.98 Hz), 7.28 – 7.38 (2H, m), 7.41 (1H, dd, J = 1.71, 7.56 Hz), 7.46 (1H, dd, J = 1.71, 7.56 Hz), 7.61 (1H, dd, J = 1.83, 8.17 Hz), 7.68 (1H, d, J = 8.54 Hz), 8.01 (1H, d, J = 1.46 Hz), 9.42 (1H, s), 11.08 (1H, s)

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
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