Category: indolines-derivatives

Electric Literature of 65435-04-3, 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. 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 9.3 g 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80-90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solid was dissolved in 90 mL of 2.5 N sodium hydroxide and stirred at 70-80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.

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, 5-(2-Chloroacetyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
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Electric Literature of 181140-34-1, 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compounds 3-7 have been synthesized using a procedure originallyreported by Roehrig et al.16 Chiral amine or amino alcohol(0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

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

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
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Application of 40314-06-5,Some common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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 5-1Preparation of 2-(5-bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one Step 1 A mixture of 5-methylisoindoline-1,3-dione (5.00 g, 31.0 mmol) and tin shavings (8.84 g, 74.5 mmol) in acetic acid (30 mL) and concentrated hydrochloric acid (15 mL) was heated at reflux for 3 h. The hot solution was filtered and the residual tin shavings were washed with acetic acid. The filtrate was concentrated and the residue was diluted with DCM (200 mL), and washed with water (20 mL) and brine (20 mL), dried and concentrated. The precipitate which formed during the concentration was collected by filtration and washed with DCM (5 mL) and dried under vacuum to give 5-methylisoindolin-1-one (2.3 g, 50%). 1H NMR (400 MHz, chloroform-d) delta 7.70 (1H, d, J=7.77 Hz), 7.43 (1H, s), 7.35 (1H, d, J=7.77 Hz), 4.46 (2H, s), 2.48 (3H, s). Mass spectrum m/z 148.0 (M+H)+.

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

Reference:
Patent; Bristol-Myers Squibb Company; US2010/160303; (2010); A1;,
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Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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. SDS of cas: 923590-95-8

Step 4: 1-t-Butyl 2-methyl (2S,4R)-4-(11(4-bromo-1,3-dthydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboicylate To a solution of (2S,4R)-B0C-4-hydroxyproline methyl ester (126.3 g, 515 mmol) in DMF (960 mL) at 0 C. was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at room temperature for 3 h. 4-Bromoisoindoline hydrochloride (120 g, 515 mmol) and diisopropylethylamine (96.3 mL, 540 mmol) were added and the reaction mixture heated to 50 C. for 6 h then allowed to cool to room temperature and stirred overnight The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+14)* ; calcd for C20H20BrN2O6: 471.1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 923590-95-8, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; US2010/160403; (2010); A1;,
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Electric Literature of 1127-59-9, The chemical industry reduces the impact on the environment during synthesis 1127-59-9, name is 7-Methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of isatin (0.14 g, 1mmol), 5,5-dimethylcyclohexanedione (0.14 g, 1 mmol), 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one (0.22 g, 1 mmol) and H3PW12O40 (0.06 g, 3 molpercent) in dry acetonitrile (5 ml) was refluxed. The reaction progress was monitored by thin-layer chromatography (eluent: ethylacetate/hexane (2:1)). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with acetonitrile (10ml). The obtained crude mass was purified by column chromatography over silica gel using ethylacetate/hexane (1:1) as eluent to give the desired product.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jannati, Saeideh; Esmaeili, Abbas Ali; Tetrahedron; vol. 74; 24; (2018); p. 2967 – 2972;,
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Related Products of 15362-40-0, 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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The desired compounds 2(a-d), 3(b-d) and 4(b-d) were procured by subjecting an equivalent mixture of compounds 9 (a-d) (1 mmol) and an active methylene compound- barbituric acid, oxindole and indolinone (1 mmol), respectively in methanol (2 mL) using catalytic amount of piperidine to microwave irradiations at 120 oC for 30 min. The reaction was monitored by TLC after every 10 min. The yellow solid obtained was filtered followed by washing with methanol and dried in air.

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-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kaur, Manpreet; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 29; 1; (2019); p. 32 – 35;,
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Reference of 603-62-3, A common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, 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.

The preparation of 2-amino-6-nitrobenzoic acid was carried out in accordance with the literature (R. Kahn, Chem. Ber. 1902, 35, 3857-3884; W. S. Saari, J. E. Schwering, J. Heterocycl. Chem. 1986, 23, 1253-1255) via regioselective opening of 3-nitrophthalimide with aqueous potassium hydroxide to give phthalamic acid and subsequent Hofmann degradation with sodium hypobromite to give the 2-amino-6-nitrobenzoic acid.

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

Reference:
Patent; Gruenenthal GmbH; US2008/293749; (2008); A1;,
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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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 7-Chloroisatin

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 °C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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 7477-63-6.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
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Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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: C11H9NO3

In a 10 ml reaction tube, adding phosphine nitrogen ligand L10a (0.35 mg, 0 . 65 mumol) with the three-phenyl phosphorus is great (0.48 mg, 0 . 50 mumol), system through the vacuum line, replace the nitrogen 3 times, and steams newly added new degassed toluene 2 ml, solution in 90 C under stirring 3 hours, cooling to room temperature, solvent is removed under reduced pressure. At the same time in another 10 ml hydrogenation bottle, adding beta – aminoketone laq (40.6 mg, 0.2 mmol) with anhydrous sodium carbonate (2.12 mg, 0 . 02 mmol), system through the vacuum line, replace the nitrogen 3 times. A syringe has been coordination of the new catalyst for steaming and new degassing of ethanol (3 ml) containing dissolved out and injected into the substrate and additive in the reaction tube, the reaction system is put in an autoclave, in 25 C and H2(50 Bar) is stirred under the condition 24 hours, the solvent is removed under reduced pressure, taking a small amount of the mixed system is nuclear magnetic resonance to determine the conversion rate. The rest of the survivor column chromatography separation, to obtain the pure product 2 aq. The conversion is 100%, enantiomeric excess is 92%. 2 Aq: white solid. According to the embodiment 1 – 12 and not the result of the symmetrical field of catalytic hydrogenation of the well known common sense, can without any doubt be inferred in this embodiment of the product structure is shown in formula (II) of the structure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2436-29-5, its application will become more common.

Reference:
Patent; Shanghai Jiao Tong University; Shanghai Zizhu Rising Industrial Technology Institute; Zhang Wanbin; Liu Delong; Wang Yanzhao; Jiang Xiuchen; Cao Lingyu; (32 pag.)CN105085372; (2018); B;,
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Related Products of 2518-24-3, A common heterocyclic compound, 2518-24-3, name is 4-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

4-Aminoisoindoline-1,3-dione (2, 2.00 g, 12.3 mmol) was dissolved in MeOH(200 mL), and the solution was treated with N-bromosuccinimide (2.19 g,12.3 mmol). The reaction was stirred at room temperature for 50 min. The solid thatprecipitated was collected by filtration and washed with MeOH to give bromide 3(2.21 g, 9.21 mmol, 75%) as a yellow powder, mp 287-289C. 1H NMR (DMSOd6):d 11.1 (s, 1H), 7.51 (d, J D 8.9 Hz, 1H), 6.90 (d, J D 8.9 Hz, 1H), 6.53 (br s,2H); 13C NMR (DMSO-d6): d 170.0, 167.7, 146.5, 139.6, 130.2, 123.6, 112.4, 101.6;MS: m/z 240, 242 (C8H5BrN2O2, MC¢, ca. 1:1).Anal. Calcd for C8H5BrN2O2: C, 42.51; H, 1.78; N, 6.20. Found: C, 42.63; H, 1.86;N, 6.14.

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:
Article; Gnanasekaran, Krishna Kumar; Rivera, Mario; Bunce, Richard A.; Organic Preparations and Procedures International; vol. 50; 3; (2018); p. 372 – 374;,
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