Author: Jessica.F

Some common heterocyclic compound, 105310-75-6, name is cis-2-((1,3-Dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide, molecular formula is C23H24N2O3, 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. Product Details of 105310-75-6

In a round bottom flask, 450ml of 40% aqueous methylamine solution was charged and 1 OOg of compound of formula III, prepared as in Example 1 , was added at about room temperature. Then the temperature was raised to about 40C to about 45C and stirred for about 2h. The reaction mixture was cooled to about room temperature and 700ml of toluene was added and stirred for about 30min. The layers were separated and the aqueous layer was extracted twice with each 200ml of toluene. The organic layers were combined and washed with 200ml of water followed by washing with 100ml of 20% aqueous sodium chloride solution. The organic layer was distilled out under reduced pressure at about 50C to about 55C, until substantially all of the solvent was distilled out. The crude was cooled to about room temperature and 350ml of ethyl acetate was added and stirred the contents for about 15min. Then 5g of activated charcoal (5g of charcoal in 50ml of isopropanol) was added to the solution and stirred for about 30min at about room temperature. The solution was filtered through Hyflo bed and the Hyflo bed was washed with 50ml of ethylacetate. The solution was cooled to about 20C and 93g of 12% w/w hydrogen chloride solution in ethylacetate was added at about 20C to about 25C over a period of about 30min and the contents were stirred for about 2h at about 20C to about 25C. The precipitated product was filtered and washed with 100ml of ethylacetate. The product was dried at about 55C to about 60C under vacuum for about 6h to yield 50g of milnacipran hydrochloride.Purity by HPLC: 99.1%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105310-75-6, its application will become more common.

Reference:
Patent; GLENMARK GENERICS LIMITED; JAMBUKAR, Nagambar Genuji; GHARPURE, Milind; SINARE, Sudam Nanabhau; THOMBRE, Pravin Chhaburao; KHAN, Mubeen Ahmed; WO2011/158249; (2011); A1;,
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Application 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 R12 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRUNDL, Marc; MORSCHHAEUSER, Gerd; OOST, Thorsten; PAUTSCH, Alexander; WO2014/140078; (2014); 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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 7-Fluoro-1-methylindoline-2,3-dione

Add beta-bromocycloalkenyl formaldehyde (131.2 mg, 0.75 mmol), N-methyl-7-fluoroisatin (89.6 mg, 0.5 mmol), thiazole salt (18.6 mg, 0.05 mmol) to a dry Schlenk tube. , Cesium carbonate (162.9 mg, 0.5 mmol), dioxane (5 mL), and heated under reflux for 12 hours. After the reaction was completed, the reaction solution was cooled and the solvent was removed by rotary evaporation. The product was separated by silica gel column chromatography (petroleum ether / ethyl acetate = 4/1) to obtain 100.0 mg of the product as a pale yellow solid with a yield of 73%.

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Institute of Technology; Wang Gang; Wu Jiang; Cheng Xing; He Zhaolin; Yuan Xiangfu; Xi Jiangbo; (9 pag.)CN110698490; (2020); A;,
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Related Products of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Mg(ClO4)2 (10 mol percent) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50percent, v/v, 5 mL), and the resulting mixture was stirred at 50¡ãC for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 ¡Á 30 mL) and cold aqueous ethanol (2 ¡Á 1 mL) to afford pure product 4.

The chemical industry reduces the impact on the environment during synthesis 7-Chloroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
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Application of 39603-24-2, 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. 39603-24-2 name is 5,7-Dimethylindoline-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: Isatin (1mmol), 1,3-indanedione (1mmol), ethyl acetoacetate (1mmol), and NH4OAc (1mmol) were placed in a 25-mL round-bottomed flask in ethanol:water (9:1) (5mL). The resulting mixture was stirred at room temperature for time mentioned in Table 2, until completion of the reaction as monitored by thin-layer chromatography (TLC). After completion of the reaction, the mixture was filtered and washed with a small quantity of ethanol to furnish pure spiro[4H-indeno-[1,2-b]pyridine-4,3′-[3H]indoles]. The structure of products was confirmed by IR, 1H and 13C NMR, GCMS, HRMS, and elemental analysis.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,7-Dimethylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Dige, Nilam C.; Pore, Dattaprasad M.; Synthetic Communications; vol. 45; 21; (2015); p. 2498 – 2510;,
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13220-46-7, name is 4-Methylindolin-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. Safety of 4-Methylindolin-2-one

(S)-5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 78f (40 mg, 0.12 mmol 1) and 4-methyl-1,3-dihydro-indol-2-one (18 mg, 0.12 mmol) were dissolved in 1.5 ml of ethanol, and added with 6mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45C for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml¡Á2) and dried to obtain the title compound (S,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylide ne)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 83 (35 mg, yield 63.6%) as a yellow solid. MSm/z(ESI): 465.2(M+1) 1NMR(400 MHz, DMSO-d6) delta13.715(s, 1H, pyrrole-NH),10.934(s, 1H, indole-NH),7.572(s, 1H, -CH=C), 7.057 (t, 1H, -ArH), 6.840?6.821(d, 1H, -ArH), 6.790?6.771(d, 1H, -ArH), 4.737?4.725(d, 1H, -OH), 3.92(m, 1H, -CHOH), 3.75 (dd, 1H, seven-membered ring intra amide -NCH2), 3.58(t, 4H, morpholin2¡Á-CH2O), 3.441 (m, 2H, seven-membered ring -NCH2), 3.15(m, 1H, seven-membered ring outer amide-NCH2), 2.939(t, 2H, -CH2CH=C), 2.594(s, 3H, pyrrole-CH3), 2.426 (m, 4H, morpholin intra 2¡Á-CH2N), 2.388(s, 3H, pyrrole-CH3), 2.309?2.293(m, 2H, morpholin outer-NCH2), 2.078(m, 2H, seven-membered ring CH2-CH2-CH2)

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
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Application of 3335-98-6, 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. 3335-98-6 name is 1-Phenyloxindole, 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: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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Adding a certain compound to certain chemical reactions, such as: 15861-23-1, name is Indoline-5-carbonitrile, 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 15861-23-1, name: Indoline-5-carbonitrile

A mixture of the compound of Part D (0.3 g, 0.72 mol) and 5-cyanoindoline (0.1 g, 0.694 mmol) in 2.5 mL 1,2-dichloroethane was stirred under N2 for 10 min, followed by the addition of sodium triacetoxyborohydride (0.22 g, 1.04 mmol, 1.5 eq.). The mixture was then stirred overnight at rt. The reaction was quenched by addition of water and 1M NaOH and extracted 3¡Á with CH2Cl2. Extracts were combined, washed with brine and dried over anh. Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 75:25) provided the desired alkylated product as a white foam (120 mg, 32%). 1HNMR (300 MHz, CDCl3) delta 8.27 (s, 1H); 7.93 (d, 1H); 7.30 (6H, m); 7.13-7.02 (6H, m); 6.18 (1H, bt), 5.88 (d, 1H, J=6 Hz); 5.03 (2H, dd, J=18, 10.8); 3.96, (s, 2H); 3.32 (t, 2H, J=6 Hz); 2.81 (t, 2H, J=6 Hz); 1.92 (m, 1H); 1.00 (6H, d, J=6.6 Hz). MS m/z 544.3 (M+H)+.

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; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); 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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H7NO2

The product of preparation 97 (5.0 g, 15 mmol), N-vinylphthalimide (2.62 g, 15.1 mmol), tri-ortho-tolylphosphine (473 mg, 1.55 mmol), palladium (II) acetate (98 mg, 0.4 mmol) and N, N-diisopropylethylamine (30 mL, 172 mmol) in acetonitrile (35 mL) was heated under reflux for 16 hours. The reaction mixture was then cooled to room temperature and the precipitate was filtered off. The solid was then dissolved in dichloromethane, activated charcoal was added, and the solution was filtered through CeliteNo.. The filtrate was concentrated in vacuo and the residue was re-crystallised from hot dichloromethane/methanol to afford the title compound as a yellow solid in 55% yield, 3.5 g. H NMR (400MHz, CDCI3) 6 : 2.20 (6H, s), 3.80 (2H, s), 4.30 (2H, d), 6.0 (1H, brs), 6.90 (2H, m), 7.01 (1H, m), 7.18 (1H, m), 7.26-7. 40 (4H, m), 7. 56-7. 61 (1 H, m), 7.75 (2H, m), 7.88 (2H, m)

According to the analysis of related databases, 3485-84-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/92840; (2005); A1;,
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These common heterocyclic compound, 59-48-3, name is Indolin-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. Product Details of 59-48-3

To a solution of oxindole (26 g) in 100 mL of concentrated sulfuric acid at -15 C. was added fuming nitric acid (8.4 mL) dropwise. Careful attention was paid to maintain the reaction temperature at -15 C. After the addition was complete, the reaction was stirred for 30 minutes and then poured into ice water. A yellow precipitate was formed which was isolated by filtration to provide 34 grams (98%) of 5-nitro oxindole.

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

Reference:
Patent; Pfizer Inc; US2005/256144; (2005); A1;,
Indoline – Wikipedia,
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