Author: Jessica.F

Synthetic Route of 14192-26-8, These common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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.

Room temperature, 2-indolone-6- methyl formate(5-2) (4.0g, 20 . 71mmol) suspended in 12 ml in toluene of, the chloroactic anhydride (5.4g, 30 . 95mmol) into the above-mentioned suspension, heating reflow 3h, cooling to 80 C, 30 min by adding methyl cyclohexane (6 ml), stirring suspension of cooling to room temperature, filtered to obtain crude products, with cold methanol (4 ml) washing, drying the white solid obtained 5.155g (93.5%), i.e. compound 1-cholroacetyl- 2-indolone-6- methyl formate (6-2).

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Chen, Yuanwei; Xie, Yongmei; Wei, Yuquan; (32 pag.)CN104003925; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 222036-66-0, name is 5-Aminoisoindolin-1-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 222036-66-0, category: indolines-derivatives

p-TSA monohydrate (23.12 mg, 0.122 mmol) was added to a stirred solution of 1-(4-((2-chloropyrimidin-4-yl)oxy)naphthalen-1 -yl)-3-(1 -(p-tolyl)-3-(tri methylsi lyl)-1 H-pyrazol-5-yl)urea (see Example 6(i) above; 33 mg, 0.061 mmcl) and 5-aminoisoindolin-1-one (18.01 mg, 0.122 mmol) in THFDMF (1 mL, 1:1). The resulting mixture was heated at 60 °C overnight. The reaction was cooled to rt then diluted with EtOAc (15 mL). The suspension was filtered, the product was detected in the filtrate which was subsequentlyconcentrated in vacuo. The crude product was purified by chromatography on silica gel (12 g column, 0-10percent MeOH in DCM) to afford a white solid. The crude product was purified by preparative HPLC (Waters, Acidic (0.1percent Formic acid), Waters X-Select PrepC18, 5 pm, 19×50 mm column, 35-75percent MeCN in Water) to afford the title compound (7 mg) as a white solid.1H NMR (DMSO-d6) 400 MHz, O: 9.93 (s, 1H), 9.24 (s, 1H), 8.84 (s, 1H), 8.47 (d, 1H),8.22 (s, 1H), 8.11 (d, 1H), 8.00 (d, 1H), 7.82-7.80 (m, 1H), 7.65-7.61 (m, 1H), 7.58-7.54(m, 1H), 7.53-7.36 (m, 6H), 7.34-7.25 (m, 2H), 6.70 (d, 1H), 6.65 (s, 1H), 3.99 (s, 2H),2.41 (s, 3H), 0.27 (s, 9H).LCMS mz 655 (M+H)+ (ES+).

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; RESPIVERT LIMITED; TOPIVERT PHARMA LIMITED; FYFE, Matthew, Colin, Thor; MEGHANI, Premji; THOM, Stephen, Malcolm; WO2014/33449; (2014); A1;,
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Application of 954-81-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 954-81-4 as follows.

8.7ml (6 · 5 X 102 moles) 1,5-dibromopentane with6 g (3. 2 X 10 2 moles) Phthalimide potassium salt dissolved in 100ml of N, N- dimethylformamide andunder room temperatureit was stirred for 15hours.The solvent was distilled off under reduced pressure, The residue usingn-hexane: ethyl acetate with a volumeratio of 10: 1 eluent to carry out column chromatography, gradually increasingthe polarity to hexane: ethyl acetate with a volume ratio of 5: 1 to give a product of 6.9g(2.3X102 mol) a bromogroup substituted by Phthalimide. The product with 5. 9g (4. 7X 102 mol) of sodium sulfite, 140ml water and 85ml95% ethanol mixed reactionwas heated to 95 C for18h, the remainingsolvent was drained, and the resulting residue was mixed with 73ml ofconcentrated hydrochloric acidthen was heated to 110 C thefor 18H, it was drained, with water – 95% ethanol on the residue to carry out recrystallization to give 5-amino-1-pentylSulfonic acid 2. 7g (total yield 50%).

According to the analysis of related databases, 954-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Institute of Chemistry Chinese Academy of Sciences; zhao, jingquan; DENG, HONG; XEI, JIE; (16 pag.)CN101948412; (2016); B;,
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Reference of 7699-18-5, 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. 7699-18-5 name is 5-Methoxyindolin-2-one, 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: Compounds 8 and 10 were prepared from azo coupling of aryldiazonium salts 3a,b with5-methoxyindolin-2-one 2, previously described [24]. Aryldiazonium salts were prepared startingto corresponding amines (21.5 mmol) in HCl 6N (11 mL) with water solution (7.5 mL) of sodiumnitrite (23 mmol). This solution was added to solution of indol-2-one (21.5 mmol) and sodium acetate(43 mmol) in methanol (59 mL) at 0 C. The resulting precipitate was filtered and purified.

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

Reference:
Article; Purgatorio, Rosa; De Candia, Modesto; De Palma, Annalisa; De Santis, Francesco; Pisani, Leonardo; Campagna, Francesco; Cellamare, Saverio; Altomare, Cosimo Damiano; Catto, Marco; Molecules; vol. 23; 7; (2018);,
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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. 3484-35-3, name is 5-Methylindolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (3a-3h, 8a-8f) (0.003 mol) in 1,4-dioxane (15 ml) was added HC(OEt)3 (2 ml) and BF3·Et2O (2 ml). The reaction mixture was heated to 80 C and stirring was continued at the same temperature for 4 h. The resulting 2-ethylthio-3-substituted-5-benzylidene-4-thiazolium fluoroborate (4a-4h, 9a-9f) was precipitated, filtered off, and dried without any additional purification, as starting material for the following reactions. To a mixture of thiazolium fluoroborate (4a-4h, 9a-9f) (0.003 mol) and indolin-2-one (11a-11f) (0.003 mol) in acetonitrile (15 ml) was added triethylamine (0.91 g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at the same temperature. The orange precipitate was collected and washed with ethyl acetate (8 ml). The crude product thus obtained was recrystallized from methanol or acetone to give compound (5a-5s, 10a-10s).

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; Wang, Shuobing; Zhao, Yanfang; Zhang, Guogang; Lv, Yingxiang; Zhang, Ning; Gong, Ping; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3509 – 3518;,
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These common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-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. SDS of cas: 446292-08-6

210.7 g (0.5 mol) of (S)-2-{[2-oxo-3-(4-(3-oxomorpholine)phenyl]oxazolidine-5-yl] prepared in Example 7 was added to the reaction flask. Methyl isonon-1,3-dione (formula VII), 1500 ml of anhydrous ethanol, and 500 ml of a 30% aqueous solution of methylamine were stirred well.The reaction was heated to 40C to 60C for 8 hours, and TLC control (dichloromethane:methanol = 20:1, volume ratio) was completed.Adjust pH to 1-2 with 10% hydrochloric acid.A large amount of white solids precipitated and cooled to about 15C.Stir for 2 hours, filter and filter cake washed with 300 ml absolute ethanol.Drying under reduced pressure gave 147.0 g of a white solid (formula VIII) in a molar yield of 89.7%. The HPLC purity was 98.7%.

The synthetic route of (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Peking University Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Xu Hong; Tian Juan; Zhang Zheng; Wang Wei; Ren Juan; (16 pag.)CN105085508; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-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 2058-72-2, category: indolines-derivatives

General procedure: A mixture of corresponding compound 1(0.5 mmol), isatin 3 (0.5 mmol), and sarcosine (0.5 mmol) in acetonitrile (40 mL) (for 1a-c) or in amixture of acetonitrile (30 mL) and chloroform (10 ml) (for 1d-f) was refluxed with stirring for 36 or 72 h for starting compounds 1a-c and 1d-f, respectively. Then the reaction mixture was cooled to room temperature, the precipitate of compounds 4a-e,j,o was filtered off and washed with acetonitrile and water. The reaction mixture of compounds 4f-i,k-n,p-t was concentrated on a rotary evaporator to half of an original volume. After cooling, the precipitate was filtered off and washed with water. Recrystallization from acetonitrile or methanol (4n) gave dispirocompounds 4a-t.

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-Bromo-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Izmest’ev, Alexei N.; Gazieva, Galina A.; Sigay, Natalya V.; Serkov, Sergei A.; Karnoukhova, Valentina A.; Kachala, Vadim V.; Shashkov, Alexander S.; Zanin, Igor E.; Kravchenko, Angelina N.; Makhova, Nina N.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2240 – 2249;,
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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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17702-83-9

a) Preparation of 8-pyrrolidinyloctylphthalimide 8-Bromooctylphthalimide (517 mg; 2.0 mmoles) and pyrrolidine (0.33 ml; 4.0 mmoles) were dissolved in anhydrous ethyl ether (5 ml). Reaction times and process as per Example 1. 348 mg of pure product were obtained. Yield 53percent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 17702-83-9.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, name: 7-Fluoroisatin

(E) -N-Benzyl-2-nitro-N-phenylethylene-1,1-diamine (1 mmol) was added to a 25 ml round-And 7-fluoroindoline-2,3-dione (1.1 mmol) were added, toluene (15 ml), trichloroacetic acid (1 mmol)Mix with heating to 110 , the reaction was refluxed for 14 hours. TLC monitoring reaction until the point of complete disappearance of raw materials, the reaction solution was added50 mL of methylene chloride and 50 mL of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous Na 2 SO 4 and theThe dried organic phase was concentrated under reduced pressure to dryness, and then 3 ml of acetone and 4 g of 100-200 mesh silica gelMix well, evaporated to dryness under reduced pressure, the sample was separated by silica gel column eluted with petroleum ether / ethyl acetate = 7: 1 to obtain a red solidThe product N-benzyl-8-fluoro-3-nitro-2- (phenylamino) quinoline-4-carboxamide (Compound 39) was obtained in 70% yield.

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; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 2-bromoaniline or 3-bromoaniline (110 mmol, 18.9 g), chloral hydrate (118.8 mmol,19.6 g), anhydrous sodium sulfate (880 mmol, 125 g), and hydroxylamine hydrochloride (347.6mmol, 24.2 g) in water (700 mL) was heated under reflux for 25 min to form a yellow precipitate. 50mL of ethanol was added after that and left to boil for another 4 min before filtration. The resultedisonitrosoacetanilide was then heated with sulfuric acid (150 mL) at 70 C for about 10 min thenpoured into ice water to form an orange precipitate. When using 3-bromoaniline, an extra step ofseparation is required by solving the resulted mixture in 0.25 M NaOH (1 L), filtering it, then addingacetic acid (100 mL) to afford 4-bromoistain as a precipitate. 6-Bromoistin can be then obtained whenlowering the pH of the solution to 1 by hydrochloric acid 37%.All substituted bromo-isatins were methylated by stirring (22 mmol, 4.97 g) with sodiumhydride (2 mmol, 0.968 g) and dimethylsulfate (23.1 mmol, 2.19 mL) in dried DMF (50 mL) undernitrogen atmosphere. The resulting mixture was poured after 2 h in ice water (100 mL) to form anorange precipitate.The methylated bromo-isatins (2 mmol, 0.480 g) were treated after that with oxindole (2 mmol,0.226 g) in a 100:1 mixture of glacial acetic acid and hydrochloric acid 37% (12 mL) in reflux for about 3 h. Then, they were poured in ice water (50 mL) to afford 5-, 6- and 7-bromomeisoindigo. While 4′-, 5′-, 6′- and 7′-bromomeisoindigo were obtained by reacting unmethylated bromo-isatins(2 mmol, 0.452 g) with 1-methyloxindole (2 mmol, 0.294 g) in the same conditions. The resultedprecipitates were washed with water, ethanol (2 x 10 mL), and diethylether (2 10 mL) then dried.

The synthetic route of 6-Bromoisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tegethoff, Jana; Bischoff, Roland; Saleh, Sawsan; Blagojevic, Biljana; Merz, Karl-Heinz; Cheng, Xinlai; Molecules; vol. 22; 9; (2017);,
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