Author: tianli

2058-74-4, A common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, molecular formula is C9H7NO2, 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: A mixture of isatin derivatives (1a-1d, 1 mmol) oracenaphthoquinone (5, 1 mmol), methylene nitriles (2a,2b, 1 mmol), 1,3-dicarbonyl (3, 1 mmol), and 5 mg IG in3 cm3 H2O was stirred at 60 C for the mentioned timeshown in tables. Rapid conversion of reagents can beclearly confirmed by reaction color change. The progress ofthe reaction was monitored by TLC using EtOAc/n-hexane(1:3) as an eluent. Upon completion, the reaction mixturewas allowed to cool to room temperature and the precipitatewas obtained from the reaction mixture by filtration.The product 4a was dissolved in DMSO and the catalystwas separated by simple filtration. Pure products wereafforded by evaporation of the solvent under reduced pressure.

The synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Javanshir, Shahrzad; Saghiran Pourshiri, Nassim; Dolatkhah, Zahra; Farhadnia, Mohammad; Monatshefte fur Chemie; vol. 148; 4; (2017); p. 703 – 710;,
Indoline – Wikipedia,
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3484-35-3, Adding a certain compound to certain chemical reactions, such as: 3484-35-3, name is 5-Methylindolin-2-one, 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 3484-35-3.

General procedure: The reaction mixture of the substituted oxindole (1 equiv), the substituted salicylaldehyde (1.2 equiv) and piperidine (0.1 equiv) in ethanol (1-2 mL/1 mmol) was stirred at 90 C for 3-5 h. After the reaction mixture cooled down, the precipitate was filtered and washed with cold ethanol and diethyl ether, successively. Allowed to dry, the product was used in subsequent reaction without further purification.

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Lidan; Ren, Wen; Wang, Xiaoyan; Zhang, Jiaying; Liu, Jie; Zhao, Lifeng; Zhang, Xia; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1071 – 1082;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1074-82-4 name is Potassium 1,3-dioxoisoindolin-2-ide, 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. 1074-82-4

The phthalimide potassium salt (2.0g, 10 . 7mmol) with 1, 4 – dibromo butane (2.8g, 12 . 9mmol) dissolved in 25 ml dry N,N-dimethylformamide in, for pH 10, room temperature stirring 26h. Dichloromethane is used for extraction three times (100 ml ¡Á 3), washed with distilled water, combined with the organic layer, drying by anhydrous magnesium sulphate, concentrated, dichloromethane/distilled water recrystallization, filtering, drying to obtain the white solid, yield of 92.4%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium 1,3-dioxoisoindolin-2-ide, and friends who are interested can also refer to it.

Reference:
Patent; Shandong University; Du Lvpei; Li Minyong; Wang Beilei; (14 pag.)CN104910894; (2017); B;,
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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. 480-91-1, name is Isoindolin-1-one, A new synthetic method of this compound is introduced below., 480-91-1

Phthalimidine (1.60g, 12.0mmol) was dissolved in THF (80mL). Triethylamine (1.34g, 13.2mmol) was added dropwise and the mixture was stirred for 5min at ambient temperature. Chlorodiphenylphosphine (2.65g, 12.0mmol) was added and the mixture was stirred for three days, whereupon the white precipitate was filtered and washed with THF (2¡Á3mL). The combined filtrate and washings were evaporated to dryness (condensation of volatiles into a cold trap under reduced pressure) and the residue was recrystallized from THF (27.5mL). The white crystalline product was suitable for single-crystal X-ray diffraction. The supernatant was decanted, the white solid was washed with Et2O (3mL) and dried in vacuo to yield 2.33g (7.34mmol, 61%) of 1b. (0014) Anal. Calc. for C20H16NOP (MW: 317.3), requires: C, 75.70; H, 5.08; N, 4.41. Found: C, 75.83; H, 5.18; N, 4.43%. 1H NMR (CDCl3, delta ppm): 4.18 (s, -CH2-, 2H), 7.33 (d, J=7.54Hz, aryl, 1H), 7.38-7.50 (br. m, aryl, 11H), 7.54 (dt, J=7.45Hz, J=1.10Hz, aryl, 1H), 7.94 (d, J=7.54Hz, aryl, 1H). 13C{1H} NMR (CDCl3, delta ppm): 49.2 (d, J=7.1Hz), 123.0 (s), 124.6 (s), 128.2 (s), 128.7 (d, J=6.2Hz), 129.6 (s), 132.1 (s), 132.2 (s), 132.5 (d, J=21.1Hz), 135.7 (d, J=14.4Hz), 143.8 (s), 173.3 (d, J=17.3Hz), 31P{1H} NMR (CDCl3, delta ppm): 29.7 (s).

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; Gericke, Robert; Wagler, Joerg; Polyhedron; vol. 120; (2016); p. 134 – 141;,
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Indoline | C8H9N – PubChem

324-03-8, A common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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 mixture of 5.0 g (30.3 mmol) 6-fluoro-1 H-indole-2,3-dione in 75 mL of 33% aq. potassium hydroxide solution was added 4.67 g (53.0 mmol) pyruvic acid and this mixture was heated at 40 C for 18 hours. After cooling to room temperature 10% aq. sulfuric acid was added (pH about 1 ). The formed solid was isolated by filtration and dried in vacuum. The solid was the desired 7-fluoroquinoline-2,4-dicarboxylic acid, which was used without further purification. Yield: 6.02 g (85%) 1H-NMR (300 MHz, DMSO d6) delta (ppm) = 7.78 (ddd, 1 H), 7.99 (dd, 1 H), 8.42 (s, 1 H), 8.89 (dd, 1 H).

The synthetic route of 324-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
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A common compound: 20870-78-4, name is 5-Bromoindolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 20870-78-4

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3¡Á10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

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, 20870-78-4, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
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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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., 496-12-8

(Intermediate Example 115) 3-Amino-1-(1,3-dihydroisoindol-2-yl)propan-1-one N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (1.94 g) was added to a solution of 3-t-butoxycarbonylaminopropionic acid (1.90 g) in N,N-dimethylformamide at 0C. A solution of 2,3-dihydro-1H-isoindole (1.00 g) in N, N-dimethylformamide was added thereto. The mixture was warmed to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure, and water and dichloromethane were added to the residue. The organic phase was separated and washed with 10% citric acid solution, 4% sodium bicarbonate solution and a saturated saline solution. The product was dried over sodium sulfate anhydrous and concentrated under reduced pressure. Ether was added to precipitate crystals, and the crystals were collected by filtration and dried under reduced pressure to give t-butyl [3-(1,3-dihydroisoindole)-3-oxopropyl] carbamate (1.33 g, Y.: 55%) as pale orange crystals.

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:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; EP1595866; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4,Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, 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 stirred solution of 1,6-dibromohexane (12.3 mL, 81.0 mmol) in DMF (10 mL), was added potassium phthalate (5.0 g, 27.0 mmol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90 C for 18 h, then quenched with water (300 mL) and extracted with diethyl ether (150 mL x 2). The combined organic extracts were washed with water (100 mL x 2), followed by brine (50 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtO Ac / hexanes to afford 3-i as an off- white solid (6.3 g, 76% yield). LCMS: 310.95 (M+l).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Potassium 1,3-dioxoisoindolin-2-ide, its application will become more common.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (244 pag.)WO2018/98208; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6326-79-0 name is 6-Bromoisatin, 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. 6326-79-0

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2¡¤NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20876-36-2, name is 5-Aminoindolin-2-one, 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 20876-36-2, 20876-36-2

5-(4-Methoxycarbonylbenzamido)-2-oxindole A mixture of 82.0 mg 5-amino-2-oxindole and 131.0 mg 4-methoxycarbonylbenzoyl chloride in pyridine was stirred at room temperature for 3 hr and poured into ice water. The precipitate was filtered, washed with water and dried in a vacuum oven to give 138.0 mg of 5-(4-methoxycarbonylbenzamido)-2-oxindole (81percent yield).

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-Aminoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem