Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 60434-13-1, COA of Formula: C9H6ClNO2

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

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; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 341988-36-1, name is Methyl indoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 341988-36-1

Example 1: Synthesis and analytical data of l-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro- indole-6-carboxylic acid methyl esterl-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro-indole-6-carboxylic acid methyl ester was synthesized starting from commercial available indoline-6-carboxylic acid methylester following the general procedure A using commercial available 4-ethoxy-benzene sulfonylchloride. ESI+, m/z+l=362, found; IH-NMR (CDCl3): delta(ppm)=8.25 (s, IH), 7.8.-7.65 (m, 3H), 7.15 (d, J=2Hz; 1H); 6.90 (d; J=3Hz; 2H), 4,10-3=90 (m, 7H), 2,95 (t, J=2Hz, 2H), 1.40 (t, J=2Hz, 3H) General procedure A: Coupling of sulfonic acid chlorides to indolines0.5 mmol of the Indoline were dissolved in a mixture of 2.5 mL dry dichloromethane and 0.5 mL dry pyridine under a nitrogen atmosphere. 0.6 mmol of the sulfonic acid chloride were added. The mixture was stirred at room temperature in a sealed tube for 6.5 h. Thereafter solvent was evaporated under vacuum. The crude product was purified by preparative HPLC-MS to give the corresponding sulfonamide.

The synthetic route of 341988-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; ELARA PHARMACEUTICALS GMBH; JANSSEN, Bernd; AMMENN, Jochen; MUeLBAIER, Marcel; ALONSO, Jorge; WO2010/17827; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 35197-64-9, 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. 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, This compound has unique chemical properties. The synthetic route is as follows.

3-(3-chlorophenyl)-2-mercapto-8-methylquinazolin-4(3H)-one (1-3) was prepared as described before . 3-(3-chlorophenyl)-2-mercapto-8-methylquinazolin-4(3H)-one (1-3,211 mg, 0.70 mmol, 1.0 equiv), 2-bromo-4-(l ,3-dioxo-l,3-dihydro-2H-isoindol-2-yl)butanoic acid (3-4, 284 mg, 0.91 ramol, 1.3 equiv.), and triethyl amine (588 muL, 4.2 mmol, 6 equiv.) were dissolved in anhydrous DMF (1 mL) and stirred at 75 0C. When LCMS indicated the reaction was complete, the crude reaction mixture was partitioned between ethyl acetate and 0.1 M HCl, the aqueous phase drained and the organic layer washed twice more with 0.1 M HCl followed by brine to yield the product (3-5). LRMS m/z (M+H) 533.8 found, 533.1 required.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2009/102537; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-2-one, 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. Recommanded Product: 193354-13-1

EXAMPLE 20 3-[5-(5-Iodo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 130 mg 5-iodo-2-oxindole, and 75 muL of piperidine in 3 mL of ethanol were stirred at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 155 mg of the title compound (71%) as an orange solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.41 (s, br, 1H, NH-1′), 12.03 (s, br, 1H, COOH), 10.79 (s, br, 1H, NH-1), 8.12 (d, J=1.70 Hz, 1H, H-4), 7.65 (s, 1H, H-vinyl), 7.36 (dd, J=1.70, 7.93 Hz, 1H, H-6), 6.79 (d, J=7.93 Hz, 1H, H-7), 2.64 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.27 (s, 3H, CH3). MS m/z (relative intensity, %) 437 ([M+1]+, 100).

The synthetic route of 5-Iodoindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-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.

A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g, 0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-1,3-dione (5 g, 22 mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C. for 30 min and 3 h at RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HCl. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261 C.; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J=9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]-); IR (thin film) 1684, 3246, 606 cm-1.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171312; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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. Quality Control of 5-Nitroindoline-2,3-dione

General procedure: A mixture of isatin derivatves (1 mmole), malononitrile (1 mmole),1,3-dicarbonyl compounds (1 mmole), and Fe3+-mont. (0.05 g) in CH3CN(5 mL) was heated using an Elmasonic S 40 H ultrasonic cleaning unit at 50 C under silent condition. The progress of the reaction was monitored by TLC (EtOAc/hexane 3:7). After completion of the reaction, the catalyst was removed by filtration. Water was added to the residue. The solid which was obtained was filtered off and dried to provide pure products of the spirooxindole derivatives (4a-j) (Table 3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 611-09-6, its application will become more common.

Reference:
Article; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Pourshiva, Mina; Nia, Roghayeh Hossein; Journal of Chemical Research; vol. 39; 6; (2015); p. 314 – 317;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H7NO3

General procedure: In a 50 mL round bottom flask, CoTCPP (3 mol %) was dissolved in water (15 ml) at room temperature. Isatin 2 (1 mmol) and isatoic anhydride 1 (1mmol) were added. Due to the partial solubility of somestarting materials in water, a mixed solvent systemof water and ethanol (v/v) (5/1) was used. The reaction mixture was stirredat room temperature for the appropriate time. Thereaction mixture was extracted with ethyl acetate and the organic layer wasdried over Na2SO4 and concentrated in vacuo. The resulting crudeproduct, was purified by recrystallization from aqueous ethanol to give tryptanthrin derivatives 3a-p. All the products are reportedin the literature16,17 and the data of the products are given in thesupporting information.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; El-Remaily, Mahmoud Abd El Aleem Ali Ali; Elhady; Tetrahedron Letters; vol. 57; 3; (2016); p. 435 – 437;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Chloro-1-methylindoline-2,3-dione

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacethylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow soild, 347 mg (66%).

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; Roh, Hwa Jung; Kim, Su Yeon; Min, Beom Kyu; Kim, Jae Nyoung; Tetrahedron Letters; vol. 58; 1; (2017); p. 21 – 24;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, 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.

Preparation 1 : ferf-Butyl 2-(6-bromo-1 -oxo-2,3-dihydro-1 H-isoindol-2-yl)acetate (1439) (1440) A suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (20 g, 94 mmol) and tert-butyl 2- bromoacetate (16.94 ml, 1 13 mmol) in DMF (320 mL) was cooled in an ice bath. Sodium hydride (4.53 g, 113 mmol) was added cautiously portionwise and the reaction was allowed to slowly warm to room temperature for 3 h. The reaction was quenched by the addition a saturated solution of NhUCI (650 mL) and the crude product was extracted with DCM (2 x 650 mL). The combined organic extracts were washed with water (4 x 650 mL) and brine (2 x 650 mL). The mixture was passed through a phase separator cartridge and the organic phase was concentrated under vacuum to give the crude product (40.1 g) as a dark orange semi-solid. 30g of the crude product were purified by chromatography (Si02, 2 x 220 g column, 0-50% EtOAc in isohexane) to afford the title compound as a yellow solid (19.5 g, 77%). LC-MS: [M-tBu+H]+ = 270/272.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem