Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 4702-13-0, name is N-Phthaloylglycine, 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 4702-13-0, Product Details of 4702-13-0

Typical Procedure: To a 30-mL vial was added N-phthaloylglycine (2.05 g, 10 mmol) and SOCl2 (8 mL) and the vial was sealed. The reaction was stirred in an oil bath at 60 C for 8 h. The mixture was cooled to r.t., the SOCl2 was removed in vacuo, hexane (10 mL) was added, and the mixture was stirred for 10 min resulting in white solid. After filtration, the solid (2.0 g, 90%) was washed with hexane and used directly in the next reaction. Phthaloylglycyl chloride (2.0 g, 9.0 mmol) in CH2Cl2 (8 mL) was added dropwise to the solution of 11a (2.2 g, 7.9 mmol) and Et3N (3.0 mL) in CH2Cl2 (50 mL). The mixture was stirred at r.t. until completion of the reaction, then diluted with CH2Cl2 (150 mL). The organic phase was washed with H2O (3 ¡Á 40mL) and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The residue was purified by flash column chromatography (silicagel) to afford 10a (3.2 g, 89%) as a yellowish solid.

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Reference:
Article; Huang, Liye; Yu, Ruina; Leng, Ling; Gong, Feng; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 17; (2014); p. 2317 – 2326;,
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7699-18-5, name is 5-Methoxyindolin-2-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C9H9NO2

General procedure: 3-(Propan-2-yliden)indolin-2-one (7a): A solution of indolin-2-one (500 mg, 3.76 mmol, 1.0 equiv.) in acetone (15 mL, 0.25 M) was heated in the presence of catalytic amounts of morpholine (164 mL, 164 mg, 1.88 mmol, 0.5 equiv.) for 16 h at reflux temperature. After complete consumption of the indolin-2-one (determined by thin layer chromatography (TLC)) all volatiles were removed under vacuum. Column chromatography(column diameter 5 cm, 30 g silica, v/v (P/EA)6 : 4-1 : 1) afforded the title compound (650 mg, 3.75 mmol, 99 %) as a yellow solid. Apparent multiplets which occur as a result of accidental equality of coupling constants to those of magnetically non-equivalent protons are marked as virtual (virt.). RF 0.70 (P/EA3 : 7; UV). deltaH (CDCl3, 250 MHz,300 K) 7.96 (1H, br s, NH), 7.52 (1H, br d, 3J 7.7, H-4), 7.19(1H, virt. td, 3JE3J 7.7, 4J 1.2, H-6), 7.01 (1H, virt. td, 3JE3J7.7, 4J 1.2, H-5), 6.85 (1H, ddd, 3J 7.7, 4J 1.2, 5J 0.6, H-7), 2.62(3H, s, H-30), 2.39 (3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K)169.5 (s, C-2), 155.7 (s, C-2′), 139.3 (s, C-7a), 127.7 (d, C-6),124.6 (s, C-3), 123.9 (d, C-5), 123.0 (s, C-3a), 121.8 (d, C-4),109.3 (d, C-7), 25.4 (q, C-1′), 23.3 (q, C-3′). The NMR data match the values reported in the literature.[9] 5-Methoxy-3-(propan-2-ylidene)indolin-2-one (7g): Prepared from 5-methoxy-2-oxindole according to RP 1 on a938 mmol scale. The title compound (176 mg, 866 mmol, 92 %) was obtained as a yellow solid. RF 0.45 (P/EA1 : 1; UV). numax(ATR)/cm1 3150w, 3030w, 2938w, 2836w, 1694vs (CO),1619s, 1594w, 1479s, 1305m, 1203w. deltaH (CDCl3, 250 MHz,300 K) 8.07 (1H, s, NH), 7.14 (1H, d, 4J 1.6, H-4), 6.78-6.72(2H, m, H-6/H-7), 3.81 (3H, s, OCH3), 2.62 (3H, s, H-3′), 2.36(3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K) 169.8 (s, C-2), 156.0(s, C-3′), 155.2 (s, C-5), 133.4 (s, C-7a), 125.6 (s, C-3a), 123.4 (s,C-3), 111.9 (d, C-4), 111.8 (d, C-6), 109.3 (d, C-7), 56.1 (q,OCH3), 25.3 (q, C-1′), 23.3 (q, C-30). m/z (HRMS ESI)204.1019; [M H)](C12H13NO2) requires 204.1019.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maturi, Mark M.; Poethig, Alexander; Bach, Thorsten; Australian Journal of Chemistry; vol. 68; 11; (2015); p. 1682 – 1692;,
Indoline – Wikipedia,
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Reference of 2058-72-2, 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.

General procedure: A mixture of compound 3 (1 mmol) and the appropriate isatinderivative 4a-i (1 mmol) in absolute ethyl alcohol and catalyticamount of glacial acetic acid was heated under reflux for 4 hrs,filtered while hot and the collected solid was washed with ethanol.The crude products 5a-i were re-crystallized from ethanol/DMFmixture (3:1) to furnish the pure title compounds 5a-i in 43-94%yields.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Almutairi, Maha S.; Zakaria, Azza S.; Ignasius, P. Primsa; Al-Wabli, Reem I.; Joe, Isaac Hubert; Attia, Mohamed I.; Journal of Molecular Structure; vol. 1153; (2018); p. 333 – 345;,
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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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 59-48-3

5-(Bromo)-1,3-dihydro-indol-2-one A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (*2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96 %) as an off-white solid which was used without further purification: mp. 221-223 C.; 1H NMR (DMSO-d6) delta3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) delta36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6391907; (2002); B1;,
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Synthetic Route of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

Statistics shows that 2-Oxoindoline-5-carboxylic Acid is playing an increasingly important role. we look forward to future research findings about 102359-00-2.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, Recommanded Product: 5-Nitroindoline

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
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Application of 774-47-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 774-47-0 name is 5,6-Difluoroindoline-2,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a stirred solution of potassium hydroxide (5 equiv.) in water (4 mL/g) in an ice-water bathwas added the isatin (1 equiv.) portionwise. The reaction mixture was stirred at roomtemperature for 10 minutes, then cooled in an ice-water bath and acetone (4 mL/g) wasadded dropwise. The reaction mixture was stirred in a 70 C heating block for the specifiedtime, then was cooled in an ice-water bath and a solution of aqueous 5 M hydrochloric acidwas added dropwise until the mixture reached pH 5-6. The reaction mixture was stirred atroom temperature for 10 minutes and then filtered. The resultant solid was filtered, driedand purified as specified

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Difluoroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Lindsay-Scott, Peter J.; Barlow, Helen; Synlett; vol. 27; 10; (2016); p. 1516 – 1520;,
Indoline – Wikipedia,
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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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H8N2O2

1. 1-Cyano-6-nitroindoline To a cooled (4 C.) and stirred solution of 6-nitroindoline (3.04 g) in a mixture of glacial acetic acid (22 ml), water (11 ml) and absolute ethanol (23 ml) was added solid cyanogen bromide (2.93 g) followed by 1N aqueous sodium hydroxide solution (25 ml) over 3 minutes. The mixture was then allowed to warm to room temperature, stirred for a further 21 hours and the solid formed was collected by filtration, washed with water and dried over phosphorous pentoxide to give the title compound (2.94 g) as a solid; deltaH (250 MHz, DMSO-d6) 7.90 (1H, dd, J=8.1 and 2.2 Hz), 7.55-7.50 (2H, m), 4.23 (2H, t, J=8.4 Hz), 3.30 (2H, t, J=8.4 Hz); m/z (CI) 189 (M-).

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck, Sharp & Dohme Ltd.; US5681833; (1997); A;,
Indoline – Wikipedia,
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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. 341988-36-1, name is Methyl indoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Methyl indoline-6-carboxylate

To the solution of methyl ind line~6-carboxyiate (150 mg, 0,85 mmoi) in 5 ml acetone were added K2CO3 (351 mg, 2.54 mmoi) and 3-(triuQromethyl)benzenesuifonyi chloride (271 mu,, 1.69 mmoi). The reaction mixture was stirred at room temperature overnight. The completion of the reaction was monitored by HPLC Upon completion, the solvent was removed in vacuo. The crude product was purified by Combiflash silica gel chromatography (0-20percent of EtOAc in hexarse), which provided 277 mg (85percent) of the title compound as a colorless solid; 1H NMR (400 MHz, CDCis) 5 = 8.25 (d, J – 1.5 Hz, 1 H), 8.12 (s, 1 H), 8.00 (d, J – 8.1 Hz, 1 H), 7.84 (d, J = 7.9 Hz, 1 H), 7,74 (d.d, J =¡¤ 1.4, 7.8 Hz, 1 H), 7.66 – 7.58 (m, 1 H), 7.17 (d, J – 7.9 Hz, 1 H), 4.01 (t, J – 8.6 Hz, 2 H), 3.95 (s, 3 H), 3.00 (t, J ~ 8.6 Hz, 2 H).

According to the analysis of related databases, 341988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INTITUTE; GRIFFIN, Patrick, R.; KAMENECKA, Theodore, M.; DOEBELIN, Christelle; CHANG, Mi, Ra; (109 pag.)WO2018/52903; (2018); A1;,
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Reference of 21857-45-4, 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 23 alpha-(5-Methoxy-1-indolinyl)-m-tolunitrile An ice cold slurry of 5.89 g (42.6 mmole) of K2 CO3 and 5.3 g (35.5 mmole) of 5-methoxyindoline in 55 ml of DMF was treated dropwise with a solution of 7.28 g (37.3 mmole) of alpha-bromo-m-tolunitrile in 50 ml of DMF. After stirring for 1 hour at room temperature, the reaction mixture was concentrated under high vacuum. The residue was partitioned between methylene chloride (250 ml) and water (250 ml). The organic layer was separated, washed with 5% NaOH (300 ml), brine (300 ml), dried over Na2 SO4 and concentrated under vacuum to yield 9.28 g (98.9% yield) of alpha-(5-methoxy-1-indolinyl)-m-tolunitrile.

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

Reference:
Patent; Hoechst-Roussel Pharmaceuticals, Inc.; US4448784; (1984); A;,
Indoline – Wikipedia,
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