Month: May 2021

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 60434-13-1 as follows. HPLC of Formula: C9H6ClNO2

General procedure: To a mixture of isatin (1 equiv.) and phenyl acetylene (1.2 equiv.) in water (3 mL), CuWO4 (10 mol%) and DABCO (40 mol%) were added at room temperature and the mixture was heated at 60 C for 2 to 5 h. After completion of reaction (monitoring by TLC) mixture was cooled to room temperature and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography to give 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u).

According to the analysis of related databases, 60434-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
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Application of 6341-92-0,Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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: A mixture of isatin 1 (1.0 mmol), malononitrile or cyanoacetic ester 2 (1.0 mmol), phthalhydrazide (1.0 mmol), and NiCl2 (0.2 mmol) in PEG 600 (5 mL) was stirred at 100 C for the appropriate time (refPreviewPlaceHolderTable 2). After complete conversion as indicated by TLC, water was added and the product was extracted with ethyl acetate (2×10 ml). The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was recrystallized from ethanol to afford the pure product.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xiao-Nan; Li, Yong-Xiao; Zhang, Zhan-Hui; Tetrahedron; vol. 67; 38; (2011); p. 7426 – 7430;,
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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. 1914-02-9, name is 3,3-Dimethylindoline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3,3-Dimethylindoline

Sodium bicarbonate (5.41 g, 64.39 mmol) and3,3-dimethylindoline (0.79 g, 5.37 mmol)Was suspended in dichloromethane (10 mL)The mixture was cooled to 0 C,Acetyl chloride (0.76 mL, 10.73 mmol) was added dropwise thereto.The reaction solution was stirred at room temperature for 2 hours and then filtered. The filtrate was concentrated under reduced pressure,The title compound was obtained as a white solid (0.99 g, 97.1%).

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 1914-02-9.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
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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. 3335-98-6, name is 1-Phenyloxindole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C14H11NO

General procedure: A mixture of oxindoles (2.0102 mmol), cinnamaldehyde,a base and a prescribed amount of TIPS-b-CDwas stirred in solvents(2 mL) at 10 C. After the removal of solvent in vacuo, the residuewas analyzed by 1H NMR to determine the reaction conversion andproduct distributions. The product was isolated by silica gel columnchromatography with a hexane/ethyl acetate (4:1, v/v) eluent. 4.5.12 (E)-N-Phenyl-3-(3′-phenylallylidene)-indolin-2-one ((E)-3g) Yellow prisms: mp 158-159 C, 1H NMR (DMSO-d6) delta 6.79 (d, J=7.7 Hz, 1H), 7.16 (dd, J=7.7, 7.7 Hz, 1H), 7.28 (dd, J=7.7, 7.7 Hz, 1H), 7.40-7.50 (m, 7H), 7.51 (s, 1H), 7.56-7.61 (m, 2H), 7.82-7.89 (m, 3H), 8.17 (d, J=7.7 Hz, 1H). 13C NMR (DMSO-d6) delta 109.0, 121.5, 122.7, 123.2, 124.2, 124.4, 126.9, 127.9, 128.3, 129.0, 129.2, 129.6, 130.0, 134.4, 135.8, 136.2, 142.8, 145.8, 166.9. IR: 1699.82 (C=O). HRMS (EI) m/z calcd for C23H17NO: 323.1310, found 323.1313.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Asahara, Haruyasu; Kida, Toshiyuki; Hinoue, Tomoaki; Akashi, Mitsuru; Tetrahedron; vol. 69; 45; (2013); p. 9428 – 9433;,
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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 17702-83-9 as follows. Application In Synthesis of 2-(8-Bromooctyl)isoindoline-1,3-dione

step 1 8-(Benzoxazol-2-ylsulfanyl)-octylamine To a round bottom flask with 2-mercaptobenzoxazole (2.14 g, 14.2 mmol) andDMF (100 mL) at room temperature was added K2CO3 (2.61 g, 18.9 mmol) followed by N-(8-bromooctyl)phthalimide (4.00 g, 11.8 mmol). The resulting solution was heated to 60° C. for 0.5 h and then cooled back to room temperature. At this point, the reaction mixture was quenched with H2O (100 mL) and then diluted with EtOAc (600 mL). The organic layer was washed with 1 N HCl (60 mL), sat. aq. NaHCO3 (60 mL), and brine (60 mL) and then dried (MgSO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 20percent EtOAc/petroleum ether gradient) to afford the thioether intermediate. To this thioether intermediate (3.02 g, 7.39 mmol) in MeOH (40 mL) at room temperature was added hydrazine monohydrate (0.860 mL, 17.7 mmol) and the resulting mixture was heated to reflux. After 18 h at this temperature, the reaction was concentrated, taken up in EtOAc (300 mL), and filtered to remove insoluble materials. This phthalimide byproduct was washed with excess EtAOc, and the filtrate was washed with H2O (40 mL) and brine (40 mL). The organic layer was then dried (Na2SO4) and concentrated to afford the product (1.87 g, 57percent) as an oil; 1H NMR (CDCl3) delta1.14-1.67 (m, 12H), 1.72-1.92 (m, 2H), 2.69 (t, J=9.6 Hz, 2H), 3.32 (t, J=8.5 Hz, 2H), 7.16-7.34 (m, 2H), 7.38-7.47 (m, 1H), 7.54-7.66 (m, 1H); mass spectrum [(+) ESI], m/z 279(M+H)+.

According to the analysis of related databases, 17702-83-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Butera, John A.; Caufield, Craig E.; Graceffa, Russell F.; Greenfield, Alexander; Gundersen, Eric G.; Havran, Lisa Marie; Katz, Alan H.; Lennox, Joseph R.; Mayer, Scott C.; McDevitt, Robert E.; US6214877; (2001); B1;,
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Synthetic Route of 423116-18-1, A common heterocyclic compound, 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione, molecular formula is C15H15NO3, 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.

Sodium cyanoborohydride (48.5 g, 772 mmol) was added portionwise to a solution of 2-((4-oxocyclohexyl)methyl)isoindoline-1,3-dione (100 g, 389 mmol, Intermediate 34) in AcOH (1.0 L), and the resulting mixture was stirred at rt for 16 h. After this time, the mixture was concentrated, and the concentrate was dissolved in EtOAc. The resulting solution washed twice with a saturated aqueous NaHCO3 solution, dried with anhydrous Na2SO4, filtered, and concentrated to afford the title compound as a colorless solid, which was used in the 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; Janssen Pharmaceutica NV; Goldberg, Steven; Martin, Connor L.; Fennema, Elizabeth G.; Wolin, Ronald L.; Fourie, Anne M.; Xue, Xiaohua; (85 pag.)US2019/382350; (2019); A1;,
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Application of 3783-77-5, A common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, molecular formula is C12H11NO3, 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 mixture of 50 g of 2- (3-oxobutyl) isoindoline-1,3-dione, 14.3 g of ethylene glycol and 7.4 g of p-toluenesulfonium tetrahydrate were dissolved in 500 ml of anhydrous toluene and treated with a water separator Reflux for 24 hours. After completion of the reaction, the reaction system was saturatedNaHCO3 aqueous solution 500 ml twice. The aqueous phase was extracted twice with 500 ml of ethyl acetate. The organic phase is combined with anhydrous sulfur Dried over sodium carbonate, and the solvent was distilled off under reduced pressure to obtain a distillation residue which was recrystallized from ethanol to give 45 g of a yellow solid: 2- (2-(2-methyl-1,3-dioxolan-2-yl) ethyl) isoindoline-1,3-dione, yield: 74.8%.

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Yao Ming Kant, Immanuel New Drug Development Co., Ltd.; Yu Lingbo; Wang Ruile; Zhou Qiang; Xu Xueqin; Zhang Dawei; Bai Youyin; Chen Dongzhi; Gao Mingfei; Yao Baoyuan; Han Huaxin; Fu Xinyu; Ma Rujian; (5 pag.)CN106939001; (2017); 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. 193354-13-1, name is 5-Iodoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Iodoindolin-2-one

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 ML of methanol, 15 ML of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide.. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated.. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane).. The fractions containing product were concentrated and allowed to stand.. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

According to the analysis of related databases, 193354-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a boiling slurry of 1 mmol of imidazothiazolotriazine hydrobromide 1a and 1b and 1 mmol of an appropriate isatin 2 in 15 mL of methanol, 0.108 mL of 40% water solution of KOH was added. The reaction mixture was stirred for 2 h. The precipitate separated on cooling the reaction mixture was filtered off, if necessary recrystallized from methanol, and dried.

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

Reference:
Article; Izmest?ev; Gazieva; Kulikov; Anikina; Kolotyrkina; Kravchenko; Russian Journal of Organic Chemistry; vol. 53; 5; (2017); p. 753 – 763; Zh. Org. Khim.; vol. 53; 5; (2017); p. 741 – 750,10;,
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Application of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-oxoindoline-6-carboxylate (4.08 g) and Mel (6.12 g) in DMF (61 ml) was added at 22 C NaH (1.71 g) over a period of 1.5 h and stirring was continued for 4 h. The mixture was partitioned between aqueous hydrochloric acid (1 M) and EtOAc, the organic layer was dried, evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 100% EtOAc in n-heptane) to give the title compound (0.64 g, 13%) as a brown solid. MS (ESI, m/z): 234.5 [(M+H)+]. The second fraction contained 3,3-dimethyl-2-oxo-2,3-dihydro-lH- indole-6-carboxylic acid methyl ester (3.82 g, 82%) as brown solid. MS (ESI, m/z): 220.5 [(M+H)+].

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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