Indolines-derivatives

Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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. COA of Formula: C8H6N2O2

To 100 parts of nitrobenzene,4-aminophthalimide10 parts,And cyanuric chloride11 parts were added,And heated at 100 to 110 C. for 5 hours.After cooling it was filtered,Washed with methanol and water.And dried at 80 C. to obtain a compound represented by the formula (2)To obtain 17 parts of the intermediate (2) represented.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3676-85-5, its application will become more common.

Reference:
Patent; DAINICHISEIKA COLOR & CHEMICALS MANUFACTURING COMPANY LIMITED; IGUCHI, KAZUKI; YANAGIMOTO, HIROMITSU; (19 pag.)JP5823431; (2015); B2;,
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Application of 6341-92-0, 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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 39a rac-6-Chloro-3-hydroxy-3-pyridin-3-yl-1,3-dihydro-indol-2-one To a solution of n-butyllithium (2.0 M in hexanes, 3.45 mL, 7.5 mmol) (Aldrich) in tetrahydrofuran (3 mL) at -78 C. was added a solution of 3-bromo-pyridine (0.96 g, 8.1 mmol) (Aldrich) in tetrahydrofuran (6 mL) dropwisely. After the addition, the resulting dark solution was stirred for additional 15 minutes. A solution of 6-chloroisatin (0.5 g, 2.76 mmol) (Crescent) in tetrahydrofuran (5 mL) was added dropwisely and the crude was warmed up to room temperature and stirred at room temperature for 3 hours. The reaction was quenched with water. The mixture was extracted with ethyl acetate three times. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography to give rac-6-Chloro-3-hydroxy-3-pyridin-3-yl-1,3-dihydro-indol-2-one as a yellow solid. (Yield 0.27 g, 37%).

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

Reference:
Patent; Luk, Kim-Chun; So, Sung-Sau; Zhang, Jing; Zhang, Zhuming; US2006/293319; (2006); A1;,
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Application of 102359-00-2, The chemical industry reduces the impact on the environment during synthesis 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, I believe this compound will play a more active role in future production and life.

2-Oxoindoline-5-carboxylic acid (0.470 g, 2.66 mmol), O-(benzotriazol-1-yl)-N,N,N’,N’- TETRAMETHYLURONIUM TETRAFLUOROBORATE (1. 010 g, 3.15 mmol), 1-hydroxybenzotriazole hydrate (0.417 g, 3.09 mmol) and N, N-diisopropylethylamine (0.7 ML, 4.0 mmol) were suspended in ACETONITRILE/N-DIMETHYLFORMAMIDE, (10 mL: 2 mL), and stirred at room temperature for 30 min. 2-Methoxyethanamine (0.516 g, 6.88 mmol) was added and stirring was continued for 2 h. Saturated aqueous sodium hydrogencarbonate was added (10 mL) and the solvents were removed M vacuo. The residue was purified on a silica gel column using a gradient chloroform/methanol, (100: 1 to 1: 1), as the eluent to give 0.355 g (57% yield) of the title compound as a solid : 1H NMR (DMSO-DE, 400 MHz) 8 10.59 (s, 1 H), 8.31 (m, 1 H), 7.72 (d, J = 7 Hz, 1 H), 7.71 (s, 1 H), 6.83 (d, Y= 8 HZ, 1 H), 3.51 (s, 2 H), 3.42 (m, 2 H), 3.39 (m, 2 H), 3.24 (s, 3 H); MS (ES) TIL/Z 235 (M++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-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
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Synthetic Route of 14389-06-1, A common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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: To a mixture of 5-chloroisatin (182 mg, 1.0 mmol) and N-carboxyethylrhodanine (205 mg, 1.0 mmol) was added DMSO-d6 (3.0 mL). The reaction was followed by proton NMR until the disappearance of the starting material.

The synthetic route of 14389-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xue, Fengtian; MacKerell Jr., Alexander D.; Heinzl, Geoffrey; Hom, Kellie; Tetrahedron Letters; vol. 54; 13; (2013); p. 1700 – 1703;,
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Related Products of 20870-79-5, 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 20870-79-5 as follows.

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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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. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, A new synthetic method of this compound is introduced below., Formula: C10H9NO

A 5 mL microwave vial equipped with a stirrer bar was charged with spiro[cyclopropane-1,3?-indolin]-2?-one (20 mg, 0.125 mmol, 1 equiv) and MgI2 (1.74 mg, 6.25 mumol, 5 mol%) before being capped and purged with N2. THF (0.6 M, 0.2 mL) and trimethyl triazinane (18 muL, 0.125 mmol, 1 equiv) were then added and the reaction mixture was heated to 125 C in a sand-bath for 60 h. The reaction mixture was then cooled to r.t. before being diluted with EtOAc (5 mL) and washed with H2O (5 mL) and brine (5 mL). The organic layers were then passed through a hydrophobic frit and concentrated under vacuum before being purified (silica gel; EtOAc-petroleum ether, 50% then MeOH-CH2Cl2, 20%) to afford the desired product. Yield: 14 mg (55%); pale-yellow oil. IR (solid): 3192, 3060, 2943, 2787, 1707, 1619, 1472, 1336, 1195 cm-1. 1H NMR (400 MHz, CDCl3): delta = 8.45 (s, 1 H), 7.41 (d, J = 7.3 Hz, 1 H), 7.19 (td, J = 7.7, 1.2 Hz, 1 H), 7.04 (td, J = 7.6, 1.0 Hz, 1 H), 6.89 (d, J =7.7 Hz, 1 H), 3.11-3.00 (m, 1 H), 2.91 (s, 2 H), 2.88-2.74 (m, 1 H), 2.49 (s, 3 H), 2.41 (ddd, J = 12.5, 7.7, 4.7 Hz, 1 H), 2.12 (dt, J = 12.9, 7.5 Hz,1 H). 13C NMR (101 MHz, CDCl3): delta = 182.7, 140.1, 136.0, 127.8, 123.4, 122.9, 109.5, 66.2, 56.7, 53.6, 41.8, 38.0. HRMS (NSI): m/z [M + H]+ calcd for C12H15N2O: 203.1179; found: 203.1177.

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; Seath, Ciaran P.; Fyfe, James W. B.; Molloy, John J.; Watson, Allan J. B.; Synthesis; vol. 49; 4; (2017); p. 891 – 898;,
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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. 112656-95-8, name is 7-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 7-Nitroindoline-2,3-dione

Step 3: 2-Amino-3-nitro-benzoic acid; To a ice cold solution of 7-nitro-1 H-indole-2,3-dione (9 g, 47 mmol) in 2 M aqueous sodium hydroxide (50 ml_), 30% hydrogen peroxide (9 ml.) was added drop wise. The mixture was warmed to room temperature and stirred overnight. The mixture was carefully acidified by addition of a saturated citric acid solution. The solid precipitate was collected by filtration, washed with water and dried in a vacuum oven to get 6 g of the required product as a yellow coloured solid (70%).1H NMR (300 MHz, DMSOd6): delta (ppm) = 8.9(br.s, 1 H), 8.19(m, 2H), 6.63(m, 1 H). HPLC purity: 98 %. LCMC(-ive mode): 93% and m/z:181.9

According to the analysis of related databases, 112656-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; THUNUGUNTLA, Siva Sanjeeva Rao; SUBRAMANYA, Hosahalli; KUNNAM, Satish Reddy; SANIVARU VIJAY, Sekhar Reddy; BINGI, Chakrapani; KUSANUR, Raviraj; SCHWARZ, Matthias; ARLT, Michael; WO2010/115736; (2010); A2;,
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Reference of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: To a solution of ligand 1(11mol %) in ethanol (2 ml) was added coppersalt (10 % mol), After 5 hours the color of the solution changed from blue-green to purple. Then,dipolarophile (0.20 mmol) has been added andstirred about 30 min. Next, a mixture of isatin derivatives (0.20 mmol) and (S)-proline (0.21 mmol), in 3 ml ethanol/dichloromethane (5/1) was added to reaction mixture.After completion of the reaction (monitored by TLC), reaction was diluted withdiethyl ether and filtered through a pad of silica gel. The organic layer wasconcentrated in vacuum to furnish the products, which were recrystallized fromethanol.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Salahi, Farbod; Taghizadeh, Mohammad Javad; Arvinnezhad, Hamid; Moemeni, Mehdi; Jadidi, Khosrow; Notash, Behrouz; Tetrahedron Letters; vol. 55; 9; (2014); p. 1515 – 1518;,
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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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Quality Control of (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione

2-({(5S) -2-oxo-3-[4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl)-1,3(2H) -dione (Formula 5) were added 75 ml of ethanol and 8.1 ml of a methylamine solution (concentration in water 40%) was added.The reaction mixture was then diluted with 60In Heating, Stir at this temperature for 2 hours.Confirm that the reaction is completed, and while maintaining the temperature, dilute the solution with 50 ml of ethanol and 3.04 ml of phosphoric acid, and slowly add the solution to the reaction solution. After confirming that the crystallization of the product was initiated and cooling to 20 C, the precipitated reaction product was filtered under suction. The resulting solid was dispersed in 110 ml of methanol, refluxed for 30 minutes and stirred, and then cooled to room temperature. The resulting crystals were filtered,And dried at 50 DEG C for 4 hours to obtain 11.1 g of morpholine diphosphate (Formula 2). (Yield: 96.0%)

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; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
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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 1074-82-4 as follows. Quality Control of Potassium 1,3-dioxoisoindolin-2-ide

REFERENCE EXAMPLE 13A Production of 4-(Diphenylmethoxy)-1-piperidinepentanamine 3.70 g of potassium phthalimide was dissolved in 20 ml of N,N-dimethylformamide; 5.4 ml of 1,5-dibromopentane was added, followed by stirring at room temperature for 15 hours. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1). The desired fraction was collected to yield 4.68 g of N-(5-bromopentyl)phthalimide as an oily substance.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6627630; (2003); B1;,
Indoline – Wikipedia,
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