Category: indolines-derivatives

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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 2-(Bromomethyl)isoindoline-1,3-dione

0.021 mol (4.99 g) of 2-(bromomethyl)-1H-isoindole-1,3(2H)-dione ( Sigma-Aldrich) was added to a solution of 4.04 g (0.020 mol) of the compound XA0 obtained in substage 1.1) of Example 1 in 35 ml of acetone (Sigma-Aldrich), in an ice bath (highly exothermic reaction). Once the addition was complete, the reaction medium was stirred at ambient temperature for 3 hours and then filtered. The filtrate was concentrated under vacuum in order to obtain the expected product XA2 in the form of a yellow oil (5.84 g, yield 91%) which will be used in the following stage without purification.

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; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE TOULOUSE III – Paul Sabatier; COUTELIER, Olivier; DESTARAC, Mathias; LANGLAIS, Marvin; (16 pag.)US2019/359603; (2019); A1;,
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Synthetic Route of 6941-75-9, 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 6941-75-9 as follows.

(B) Synthesis of Compound 31-c 194 ml of fuming nitric acid (fum. HNO3) was added to 0.9 L of concentrated sulfuric acid under stirring and cooling in an ice water bath. The mixture was stirred for 1 hour under cooling in an ice water bath, and then 215 g of Compound 31-a was added slowly to the mixture in portions over 30 minutes, while an inside temperature was maintained at 15 C. or lower. After completion of the addition, the mixture was stirred at room temperature for 8 hours. The reaction liquid was poured into 1 L of ice water, to precipitate crystals. After stirring, the crystals were collected through filtration, and washed with running water. The thus-obtained crude crystals of Compound 31-b were transferred to another flask without purification. 1 L of DMF was added thereto, and the whole was stirred at room temperature. To the resultant suspension, 200 ml of 25% ammonia water was added under stirring, and the mixture was stirred at room temperature for 3 hours. The crystals were collected through filtration, and added to 1.5 L of isopropyl alcohol. The mixture was refluxed under heating for 30 minutes, and then stirred at room temperature for 3 hours. The crystals were collected through filtration, washed with running hexane, and dried, to thereby obtain 131 g (48% yield from Compound 31-a) of Compound 31-c.

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; US2006/142553; (2006); A1;,
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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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

A solution of 5-nitroindoline (1.033 g, 6.30 mmol), TEA (0.827g, 8.19 mmol) in DCM (30 mL) at 0C was slowly added methylsufonyl chloride (0.868 g, 7.56 mmol). The mixture was warmed up and stirred at room temperature for 0.5 h. The reaction was quenched with water (30 mL) and extracted with DCM (25 mL x4). The organic layers were combined, dried and concentrated under reduced pressure to afford crude 1 (1.427 g, 5.9 mmol, yield 95%), which was used for next step without further purification.

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; ACEA BIOSCIENCES INC.; XU, Xiao; WANG, Xiaobo; MAO, Long; ZHAO, Li; XI, Biao; WO2015/6754; (2015); A2;,
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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. 199328-10-4, name is Methyl Oxindole-5-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Step 2: Synthesis of 5-Carboxy-2-oxindole. 5-Methoxycarbonyl-2-oxindole (1 g) and 1 g of sodium hydroxide in 20 mL of methanol was refluxed for 3 hours. The reaction mixture was cooled and concentrated to dryness. The residue was dissolved in water and extracted twice with ethyl acetate. The aqueous layer was acidified with 6 N hydrochloric acid and the precipitated solid collected, washed with water, and dried to give 0.7 g (78%) of the title compound as an off-white solid.

The synthetic route of 199328-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
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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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 446292-08-6

20 g of 2-({(5S) -2-oxo-3-[4-(3-oxomo holin-4-yl) henyl]-1 ,3-oxazolidin-5-yl}methyl)-1H- isoindole-1,3(2H)-dione was suspended in 450 ml of ethanol, which was followed by addition of 6 ml of hydrazinehydrate in 50 ml of ethanol and the mixture was stirred and refluxed for 3 hours. Then, the suspension was cooled down to 65C and filtered and the cake was washed with 2×50 ml of nearly boiling ethanol. After drying 7.2 g of an off-white powder were obtained, which slowly melted at a temperature over 260C (this fraction contained 99.9% of 2,3-dihydrophtalazine-l,4-dione according to HPLC). After cooling of the hot filtrate another solid fraction separated. After its isolation by filtration and drying, 12.5 g of white lumpy powder with the melt, point of 141-144C was obtained (this fraction contained 86.7% of the desired product, 12.7% of 2,3-dihydrophtalazine-l,4-dione, and the rest to 100 % were other unidentifiable impurities according to HPLC). The yield of the isolated amine calculated to the pure substance was 73%.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZENTIVA, K.S.; HALAMA Ales; KRULIS Radim; DAMMER, Ondrej; KALASEK, Stanislav; WO2013/120465; (2013); 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 2058-72-2

General procedure: 11H-indeno[1,2-b]quinoxalin-11-one 2a (0.23?g, 1.00?mmol) and TosMIC (0.20?g, 1.10?mmol) was poured into the mixture of ethanol (1.00?mL) and K2CO3 (0.14?g, 1.00?mmol), and stirred for 10?min?at ambient temperature. After that, the reaction mixture was diluted with water (3.00?mL), the resulting precipitate was filtered, and washed with water.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shaabani, Ahmad; Sepahvand, Heshmatollah; Bazgir, Ayoob; Khavasi, Hamid Reza; Tetrahedron; vol. 74; 49; (2018); p. 7058 – 7067;,
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Reference of 40314-06-5, These common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-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.

Isolation and analytic data for 14, observed in the crossover study, was obtained by independent preparation using the following procedure. Benzoyl chloride (62 muL, 0.54 mmol) was added to a mixture of 4-methylphthalimide (200 mg, 1.2 mmol), isobutyraldehyde (108 muL, 1.19 mmol), NaI (160 mg, 1.1 mmol), 4 A MS (100 mg), triethylamine (150 muL, 1.1 mmol), ethyl acetate (1.1 mL), and acetonitrile (1.1 mL) at room temperature and with stirring. After 24 h, the mixture was diluted in EtOAc and washed with 1 M NaOH (3¡Á) and brine. The organic phase was dried (MgSO4) and concentrated. Purification by flash chromatography (SiO2, hexanes:EtOAc 6:1) gave 14 (145 mg, 0.43 mmol, 80%) as a yellow oil. 1H NMR (300 MHz, CDCl3): delta 8.09 (d, J=7.7Hz, 2H), 7.75 (d, J=7.6Hz, 1H), 7.67 (s, 1H), 7.50-7.60 (m, 2H), 7.43 (dd, J=7.6, 7.8Hz, 2H), 6.46 (d, J=10.4Hz, 1H), 3.09 (nfom, 1H), 2.50 (s, 3H), 1.15 (d, J=6.7Hz, 3H), and 0.96 (d, J=6.8Hz, 3H). 13C NMR (75 MHz, CDCl3): delta 167.1, 167.0, 165.3, 145.8, 135.0, 133.5, 131.9, 130.0, 129.4, 128.9, 128.5, 124.2, 123.7, 79.7, 29.8, 22.1, 19.1, and 18.0. IR (neat): 2965, 2938, 2874, 1780, 1748, 1720, 1469, 1373, 1359, 1223, and 720 cm-1. HRMS (ESI-TOF): Calcd for C20H19NNaO4+ [M+Na+] requires 360.1206; found 360.1223.

The synthetic route of 40314-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
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Application of 19155-24-9, A common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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.

3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mixture. The reaction was stirred for 50 min., then poured into water. The mixture was basified with sodium carbonate, extracted with ethyl acetate (.x.3), dried (MgSO4), filtered, and evaporated to give the subtitled compound (0.89 g, 92percent) 1H NMR (DMSO-d6) delta 1.21 (s, 6 H), 6.76 (d, 1 H, J=8.22 Hz), 7.29 (dd, 1 H, J=2.12 Hz, 8.23 Hz), 7.49 (d, 1 H, J=2.03 Hz), 10.4 (s, 1H).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6355648; (2002); B1;,
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Application of 14389-06-1, The chemical industry reduces the impact on the environment during synthesis 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

To a suspension of 3-bromo-l-(3-chloro-2-pyridinyl)-lH-pyrazole-5-carboxylic acid (see PCT Patent Publication WO 03/015519 for preparation) (97.6% purity, 13.02 g, 42 mmol) and 5-chloro-7-methylindoline-2,3-dione (K. Tsuji et al., Bioorg. Med. Chem. Letters, 2002, 72(17), pp 2427-2430) (7.82 g, 40 mmol) in dry acetonitrile (50 mL) was added 3-picoline (11.9 g, 127 mmol). The mixture was cooled to 0 C, and then methanesulfonyl chloride (6.87 g, 60 mmol) was added dropwise at 0-10 0C. After stirring 5 minutes at this temperature, the mixture was warmed to room temperature for 20 hours. The precipitated solids were filtered, washed with acetonitrile (3 x 5 mL), and dried under nitrogen to afford the title product, a compound of the present invention, as a yellow powder, 14.90 g (77.6% yield), m.p. 173-177 0C (decomp.).1H NMR (CDCl3) delta 2.16 (s, 3H), 7.14 (s, IH), 7.38 (dd, J = 8.1, 4.8 Hz, IH), 7.53 (d, /= 2.1 Hz, IH), 7.60 (d, /= 2.1 Hz, IH), 7.89 (dd, /= 8.1, 1.5 Hz, IH), 8.39 (dd, / = 4.8, 1.5 Hz, IH). The NMR spectrum also showed that some 3-picoline salts were present in the crude 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, 5-Chloro-7-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2007/24833; (2007); A1;,
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Related Products of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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.

To a solution of 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
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