Month: April 2021

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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 2436-29-5, Safety of 3-(1,3-Dioxoisoindolin-2-yl)propanal

Example 12d (0.06 g, 0.135 mmol) and 3-(l ,3-dioxoEomdoliiv2-yl)propa-ial (0082 g, 0.406 mmol) were combined in tetrahydiiofuran (1 .353 mL) under nitto gen and treated drop-wise with 1 M utanium(IV) chloride in toluene (0.406 mL, 0.406 mmol) . The reaction mixture was stirred lor 18 hours at 60 * C, cooled to artfc ient temperature, and partitioned b etwee II ethyl acetate and water. The organic layer was was lied with s aturated aqueous sodium cluotide, dried over arfoydrous sodium sulfate, filtered and concentrated. Irification b y revers e phase HPLC (C IS, C CNAvater (0.1 “A TFA), 0- 100 % gradient) provided the title compound. (0.018 g, 21 ). NMR (500 MHz, DMS O-^ 6 11 94 (d, J = 2.14 Hz, 1H1 7.88 (d, J = 1 53 Hz, 1H), 7.80 – 786 (m, 4H), 7.72 (s, 1H), 7.31 (d, J = 2.75 Hz, IK), 728 (dd, J = 3D9, 1.98 Hz, 1 H), 7.02 – 7.10 (m, 2H), 6.77 – 6.83 (m, 1H), 6.65 – 6.72 (m, 1 5.06 – 5.1 1 (m. 1H), 4.40 – 4.57 (m, 2H), 3.70 – 3.79 (m, 1H), 3 65 ( , 3H), 354 – 3.63 (m, lH), 2.95 (s, 3H), 1 91 – 2.07 (m, 1 1.62 (dd, J = 13.12, 5.19 Hz, 1H). MS (ES I+) mfe 629 (M+H) 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, 3-(1,3-Dioxoisoindolin-2-yl)propanal, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

603-62-3, name is 3-Nitrophthalimide, 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. name: 3-Nitrophthalimide

General procedure: 1 [43] (500 mmol) and 2 (500 mmol) were dissolved in acetonitrile(50 mL), then Cs2CO3 (204 mg, 625 mmol) was added in abovesolution. The resulting mixture was stirring overnight at roomtemperature under an inert atmosphere. After the reactioncompleted, the solvent was removed under vacuum and the residue was purified by silica gel column chromatography (petroleumether/ethyl acetate, 3/1, v/v).HP1, red solid, 93 mg, 36% yield;

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Biao; He, Zhaoshuai; Zhou, Hanxin; Zhang, Han; Li, Wu; Cheng, Tanyu; Liu, Guohua; Dyes and Pigments; vol. 146; (2017); p. 300 – 304;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, Product Details of 2058-72-2

General procedure: To a stirring mixture of catalyst 1a (0.005 mmol) and cyclohexanone/acetone (5 mmol) in water (500 muL), additive DNP (0.920 mg, 0.005 mmol) was added at 25 C and the mixture was allowed to stir for 5 min followed by addition of isatin derivative (0.5 mmol). The mixture was stirred for 20-96 h and the progress of the reaction was monitored at regular intervals by TLC. On the completion of reaction, saturated solution of NH4Cl (5 mL) was added to it and resulting mixture was extracted with ethyl acetate (3¡Á15 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude aldol product. The column chromatography on silica gel (60-120 mesh) using hexane/ethyl acetate as an eluent gave the corresponding aldol adducts as a syn/anti mixture. The enantiomeric excess of aldol addition products was determined by chiral HPLC. The diastereoselectivity of product was determined by HPLC of crude reaction mixture. Racemic standards were prepared using (¡À) 3-methyl-1-morpholinobutan-2-amine catalyst synthesized form (¡À) valine.

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; Kumar, Akshay; Chimni, Swapandeep Singh; Tetrahedron; vol. 69; 25; (2013); p. 5197 – 5204;,
Indoline – Wikipedia,
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. 61-70-1, name is 1-Methylindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9NO

General procedure: Isatin (0.1 mol, 14.7 g) was dissolved in DMF (60 mL) and finely ground anhydrous K2CO3 (0.15 mol,20.7 g) was added under stirring. RX (0.15 mol) was added dropwise and mixture was heated at 60-70C for 3 h (as alkylation reagent RX were used Me2SO4, EtI, n-PrBr, AmBr, BnCl, PMBCl,respectively). After cooling to room temperature mixture was poured into ice water (200 mL).Precipitated orange solid was filtereted, washed with water and recrystallized from ethanol (95%) togive N-alkylated isatins as red crystalls in 37-92% yield. The purity of obtained compounds weredetermined by melting points, which corresponded to those published in the literature (ref. 2-4).N-Substituted isatin (10 mmol) was mixed with 16 M N2H4¡¤H2O (15 mL). The suspension was heatedat reflux 3 h (caution: rapid gas evolution), then it was cooled to room temperature, diluted with waterS4(40 mL) and extracted with EtOAc (3 x 25 mL). Organic phase was washed with water (25 mL), brine (25 mL), then it was dried over Na2SO4 and evaporated under reduced pressure to give the desired product. The latter was recrystallized from hexane and small amount of EtOAc to give N-substituted indolin-2-one as yellow solid in 47-96% yield. The purity of obtained compounds were determined by melting points and 1H NMR spectra data, which corresponded to those published in the literature (ref. 5,6).N-Substituted indolin-2-one (2 mmol) were dissolved in dry DMF (5 mL) and NaH (60% dispersion in mineral oil, 6 mmol, 240 mg) was portionwise added carefully at a temperature of -15 C. When the rapid evolution of H2 stops, the mixture allowed to stir for 10 min. Then solution of 1,2-dibromoethane (508 mg, 2.7 mmol) in dry DMF (3 mL) was added to the mixture. The latter was warmed to room temperature and stirred overnight. Then it was cooled with ice, diluted with water (20 mL) and extracted with PhMe (2 x 15 mL). Organic phase was washed with water (2 x 15 mL), brine (15 mL) and then it was dried over Na2SO4. Evaporation under reduced pressure gave the desired product. The latter was washed with hexane to remove mineral oil or purified by flash column chromatography (eluent: hexane/CH2Cl2). The spiro[cyclopropane-1,3′-indolin]-2′-ones 1 are yellow solids, except N-amyl substituted spiro[cyclopropane-1,3′-indolin]-2′-one, which is brown liquid. The purity of obtained compounds were determined by 1H NMR spectra data. Corresponding cyclopropanes were previously known in the literature (ref. 7-11).

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; Buev, Evgeny M.; Moshkin, Vladimir S.; Sosnovskikh, Vyacheslav Y.; Tetrahedron Letters; vol. 59; 37; (2018); p. 3409 – 3412;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 337536-15-9 as follows. Computed Properties of C8H6BrNO

EXAMPLE 2A 4-bromo-7-nitro-1-isoindolinone A 0 C. solution of Example 1C (5 g, 23.6 mmol) in 10 mL sulfuric acid was treated with a solution of concentrated nitric acid (1.55 mL, 24.7 mmol) in 10 mL sulfuric acid via addition funnel. The resulting mixture was stirred at 0 C. for 1 hour, warmed to room temperature, stirred overnight, poured over ice, and filtered. The filter cake was washed with water and diethyl ether and then dried to give 5.39 g of the desired product. 1H NMR (300 MHz, DMSO-d6) delta 4.39 (s, 2H); 7.88 (d, J=8.1 Hz, 1H); 8.05 (d, J=8.5 Hz, 1H); 9.17 (s, 1H).

According to the analysis of related databases, 337536-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 mm at room temperature .Afier complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for I h. The resultant precipitate was filtered, washed with water (500 rnL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%).?H NMR (40() MHz, C1)Ci3): d 7.84 (dd, J= 5.5 Hz, 3.() Hz, 2K), 7.71 (dd, j:zr. 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 2.85 (t, J= 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1Ff), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M+1).

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; SHIRUDE, Pravin S.; (258 pag.)WO2017/6282; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3416-57-7,Some common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, molecular formula is C11H9NO3, 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.

2.0g of compound I is mixed with 3.76g of potassium carbonate thoroughly, then the resulting mixture is poured into a 25ml flask followed by adding 4.0ml of chloroacetone into, heating the solution to 90-110C (a reflux condensing tube is needed to be equipped on the flask, the system is protected with argon) while stirring, maintaining the temperature, and conducting the reaction for 3-4 hours. After the reaction is completed, excess chloroacetone is removed under a reduced pressure, into the residue is added a great deal of water, then filtrated with Buchner’s filter. The resulting solid is washed twice with 10ml of 10% NaOH and 5-6 times with water respectively, dried under vacuum to obtain compound II; After a reflux condensing tube and a dropping funnel are connected on a three-necked bottle, 100ml of absolute methanol (or other anhydrous solvent) is added into the three-necked bottle, followed by slowly adding 0.23g of metallic sodium (or directly adding 10mmol of sodium methoxide). After the solid dissolves entirely, the solution is heated and refluxed, then compound II dissolved in absolute methanol (60ml CH3OH and 1.0g compound II) is dropped into by dropping funnel. After conducting the reflux for 2 hours the reaction is processed as follows: cooling the system with icewater bath, slowly neutralizing the reaction solution with 1M hydrochloride, continuing to stir for 30min in icewater bath after a large amount of solid emerge, filtrating to obtain a solid, then washing the solid with small amount of water, drying in vacuum, thereby obtaining compound III. 230mg of compound III is placed in a 25ml flask followed by adding 5ml solvent (listed in the above) into, air is blown into by a bubbler continuously. The reaction is completed after 10 hours and processed as follows: diluting the reaction solution with 30ml of acetic ether, extracting with water, back-extracting the water phase with 30ml of acetic ether, washing the organic phases with water and saturated salt solution respectively, combining the organic phases, then drying, condensing, the residue is applied on silica gel column (petroleum ether: acetic ether=2:1) to obtain compound IV

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; EP1640367; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem