Tag: M.W=100-200

56341-37-8, name is 6-Chlorooxindole, 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. Product Details of 56341-37-8

General procedure: Synthesis of 6-chlorooxindole derivatives was carried out by refluxing 6-chlorooxindole with different aromatic aldehydes in ethanol in the presence of a catalytic amount of piperidine. The reaction mixture was refluxed for 3 h. After completion of reactionas determined by TLC analysis, the contents were cooled and concentrated at reduced pressure to afford solid 3-oxindole derivatives. The product was washed with equal volumes of a mixture of hexane-ethyl acetate (25 mL) and dried to afford compounds 1-25.20 1H NMR, EI spectroscopy and CHN analysis were used for the determination of their structures. 4.1.18 (E)-3-(3-Methoxybenzylidene)-6-chloroindolin-2-one (18) Yield: 0.24 g (84%); 1H NMR (500 MHz, DMSO-d6): delta 10.75 (s, 1H, -NH), 7.63 (s, 1H, =CH), 7.52 (d, 1H, J4,5 = 8.0 Hz, H-4), 7.43 (t, 1H, J5′(4′,6′) = 8.0, H-5′), 7.24(t, 1H, J4′(3′,5′) = 8.0, H-4′), 7.23 (d, 1H, J6′,5′ = 8.0 Hz, H-6′), 7.04 (d, 1H, J3′,4′ = 8.0 Hz, H-3′), 6.93 (dd, 1H, J5,7 = 1.5, J5,4 = 8.0 Hz, H-5), 6.88 (d, 1H, J7,5 = 1.5 Hz, H-7), 3.79 (s, 3H, -OMe); MS: m/z (rel. abund.%) 285 (M+, 100), 178 (59), 152 (32), 63 (56); Anal. Calcd for C16H12ClNO2 (285.72): C, 67.26; H, 4.23; Cl, 12.41; N, 4.90; O, 11.20; Found: C, 67.28; H, 4.22; N, 4.88.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Momin; Yousaf, Muhammad; Wadood, Abdul; Junaid, Muhammad; Ashraf, Muhammad; Alam, Umber; Ali, Muhammad; Arshad, Muhammad; Hussain, Zahid; Khan, Khalid Mohammed; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3441 – 3448;,
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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5-Chloroisoindoline-1,3-dione

7a: A mixture of concentrated sulfuric acid (24 mL) and fuming nitric acid (1.5 mL) was added dropwise to 4-chloro-phthalimide 6 (4.90 g, 27.0 mmol). The reaction mixture was heated at 80 C for 0.5 h. After cooling to r.t. the dark red solution was poured into ice. The resulted yellow precipitate was collected by filtration, washed with water, dried in vacuum affording a pale yellow solid 7a (3.52 g, 58% yield). 1H NMR (DMSO-d6): delta (ppm) 11.87 (s, 1H, CONHCO), 8.51 (s, 1H, Ar-H), 8.27 (s, 1H, Ar-H). 13C NMR (DMSO-d6): delta (ppm) 166.66, 166.62, 151.28, 135.96, 132.43, 130.30, 126.03, 119.62.

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Xiaoyu; Zhao, Jing; Zhang, Wandong; Chen, Long; Chinese Chemical Letters; (2018); p. 331 – 335;,
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. 6341-92-0, name is 6-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H4ClNO2

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¡Á10 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.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Xiao-Nan; Li, Yong-Xiao; Zhang, Zhan-Hui; Tetrahedron; vol. 67; 38; (2011); p. 7426 – 7430;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, molecular formula is C9H7NO3, 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. Computed Properties of C9H7NO3

The intermediate from Step D was esterified by heating in acidic methanol overnight. The resulting solution was concentrated under vacuum and the residue was dissolved in hot ethanol (75 mL). Methanol (20 mL) was added to redissolve some material that precipitated as the solution cooled. Sodium nitrite (1.50 g) was added, followed by concentrated hydrochloric acid (5 mL). The reaction was stirred for 2 h, and a further concentrated hydrochloric acid (2 mL) was added. The reaction was stirred overnight. Volatiles were removed under reduced pressure, water added, and the resulting yellow orange product was isolated by filtration and dried under vacuum to give the intermediate (2.1 g) as a yellow orange solid. [MH]+=221.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 334952-09-9, its application will become more common.

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
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. 496-15-1, name is Indoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H9N

PREPARATION 4 6-Nitroindoline 5.96 g (50 mmol) of indoline were dissolved in 25 ml of concentrated sulfuric acid, and a mixture of 3.75 ml of concentrated nitric acid (61%) and 25 ml of concentrated sulfuric acid was added to the solution while ice-cooling so that the internal temperature was maintained at 10 C. or lower. The mixture was then stirred while ice-cooling for 2 hours. At the end of this time, a 75% w/v aqueous solution of sodium hydroxide was added to the reaction mixture while ice-cooling to neutralize the reaction mixture, while maintaining the internal temperature at 60 C. or lower. The mixture was then extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and, after filtration, the solvent was removed from the filtrate by distillation under reduced pressure to obtain 7.8 g (47.5 mmol) of the title compound as crystals, melting at 65-68 C. (yield: 95%). 1 H Nuclear Magnetic Resonance (200 MHz, CDCl3) delta ppm: 3.10 (2H, triplet, J=8.5 Hz); 3.69 (2H, triplet, J=8.5 Hz); 4.04 (1H, broad singlet); 7.15 (1H, doublet, J=8.1 Hz); 7.35 (1H, doublet, J=2.1 Hz); 7.56 (1H, doublet of doublets, J=2.1 & 8.1 Hz).

The synthetic route of 496-15-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; US5773618; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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: C8H4KNO2

Into a Sovirel type reactor mechanically stirred, provided with a condenser, an opening for introduction of solids, a system for inerting with nitrogen, and a temperature probe, are loaded 5 mol (1081 g) of 1,4-dibromobutane and 1 mol (188 g; 98.5% pure) of potassium phthalimide. The reaction medium is brought under stirring to 115 C. and then kept at this temperature for 15 h. It is verified that the conversion is complete by a measurement of the potassium bromide in the reaction medium. [0048] After cooling of the reaction medium to 80 C., 200 g of water are added. After 15 min of stirring and then decantation, the aqueous phase containing the potassium bromide is removed and then a second washing is carried out (still at 80 C.) with 50 g of water. [0049] The ascending condenser is then replaced by a distillation column and then the excess 1,4-dibromobutane is distilled under reduced pressure (8-10 mbar) with a bottom temperature from 80 to 120 C. Thus, 815 g of 1,4-dibromobutane are recovered corresponding to a recovery rate of 1,4-dibromobutane of 94%. This latter with a purity greater than 99.8% may be directly recycled into a later operation. [0050] At the end of the distillation, the reaction medium is left to cool to 75-80 C. and then 325 g of ethanol are added. After homogenization and obtention of a clear organic solution at reflux of ethanol, the reaction medium is left to cool under stirring to room temperature (20 C.). [0051] After crystallization of the N-(4-bromobutyl)phthalimide, the ethanolic suspension of the product is filtered on frit at room temperature. The moist cake is washed with 35 g of ethanol and then dried at 50 C. under reduced pressure (20 mmHg). Thus, 268 g of N-(4-bromobutyl)phthalimide are obtained that correspond to a molar yield of 92% compared with the potassium phthalimide provided.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gillet, Jean-Philippe; Ruppin, Chirstophe; US2004/176613; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 102359-00-2, 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. 102359-00-2 name is 2-Oxoindoline-5-carboxylic Acid, 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: Compound 7 (2.1 g, 0.012 mol) and HBTU (5.0 g, 0.013 mol) were dissolved in dry DMF, in a 250 ml round bottom flask. DIPEA (6.5 ml, 0.037 mol) was added and the reaction mixtures were stirred for 30 min. L or D- phenylalanine methyl ester hydrochloride (3.0 g, 0.014 mol) or glutamic acid dimethyl ester hydrochloride (3.0 g 0.014 mol) was added and the reaction mixture was kept stirring overnight under ambient conditions. Reaction monitoring by TLC was performed on silica gel plates using CHCl3:MeOH 9:1 as eluent. Saturated NaHCO3 solution (150 ml) was added to the mixture and the precipitate was filtered, washed with saturated NaHCO3 solution and water. The crude product was purified by column chromatography CHCl3:MeOH (95:5) to give the product as white to off-white solid.

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

Reference:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-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 39603-24-2, Application In Synthesis of 5,7-Dimethylindoline-2,3-dione

General procedure: To a mixture of isatin 1a (14.7 mg, 0.1 mmol), H2O (5.4 muL, 0.3 mmol), quinine-derived amine 3 (3.3 mg, 0.01 mmol), and benzoic acid (3.66 mg, 0.03 mmol) in THF (1.0 mL) at 5 C was added acetaldehyde (22.0 mg, 0.5 mmol). After the reaction mixture was stirred for 15 h at this temperature, it was cooled to 0 C. Methanol (2 mL) and NaBH4 (20.0 mg, 0.5 mmol) were then added sequentially. The resulting reaction mixture was stirred for an additional 30 min at 0 C. Water (5.0 mL) was added to quench the reaction. The reaction mixture was extracted with ethyl acetate (10 mL x 3). The combined organic phases were dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:2 to 2:1) to give the pure product 2a.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Qunsheng; Zhao, John Cong-Gui; Tetrahedron Letters; vol. 53; 14; (2012); p. 1768 – 1771;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6341-92-0, The chemical industry reduces the impact on the environment during synthesis 6341-92-0, name is 6-Chloroisatin, I believe this compound will play a more active role in future production and life.

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

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

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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. 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. Safety of Indolin-2-one

Sodium hydride (9.0 g; 0.2 mol, 60% in mineral oil) was added portion-wise to a solution of oxindole (10.0 g, 75 mmol) in of dry DMF (350 mL). After 15 minutes, the reaction was cooled to 0 C. and 1,4 dibromoethane in 100 mL of dry DMF was added over 15 minutes. The dark brown reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with ethyl acetate and water was added. The layers were separated and the organic layer was dried over anhydrous sodium sulfate. The organic layer was filtered, concentrated in vacuo to give 20 g of red oil. The crude product was purified on silica using a stepwise gradient of 10% to 20% ethyl acetate: hexane to afford Spiro[cyclopropane-1,3′-[3H]indol]-2′(1’H)-one (2.3 g, 11%).

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

Reference:
Patent; Wyeth; US2006/30615; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem