Month: July 2021

Application of 496-12-8, 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. 496-12-8, name is Isoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 94 N-[5-(1,3-dihydroisoindol-2-ylcarbonyl)-1-methylpyrrol-3-yl]-4′-trifluoromethylbiphenyl-2-carboxylic Acid Amide Prepared analogously to Example 1d from 4-(4′-trifluoromethylbiphenyl-2-carbonylamino)-1-methylpyrrole-2-carboxylic acid, 2,3-dihydro-1H-isoindole, TBTU and N-ethyldiisopropylamine in dimethylformamide. Yield: 79% of theory; Rf value: 0.64 (silica gel; dichloromethane/ethanol=9:1); C28H22F3N3O2 (489.50); mass spectrum: (M-H)-488; (M+H)+=490; (M+Na)+=512.

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US2003/73836; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-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.

General procedure: Toa solution of 4a (10.0 g, 35.3 mmol)in MeOH (200 mL) was added 8M KOH solution (20 mL) and then heated to reflux.After 36 h, the reaction mixture was concentrated under reduced pressure.The mixture was diluted with H2O (100 mL), extracted with EA (75 mL×2), dried over Na2SO4 and concentrated under reducedpressure. The residue was dissolved in THF (100 mL). Di-tert-butyldicarbonate (9.0 g, 41.2 mmol) and DMAP (0.5 g, 4.0 mmol) was added and thenthe reaction mixture was stirred at room temperature for 4 h. Afterconcentration, the residue was purified by silica gel column chromatography(PET/EA = 15:1, v/v) to affordcompound 5a as colorless oil (8.3 g,75.5%).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sun, Zhaozhu; Zhou, Tian; Pan, Xuan; Yang, Ying; Huan, Yi; Xiao, Zhiyan; Shen, Zhufang; Liu, Zhanzhu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3050 – 3056;,
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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H6N2O2

EXAMPLE 104 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile A solution of 400 mg (1.44 mM) of 4-chloro-6,7-diethoxy-quinoline-3-carbonitrile and 305 mg (1.88 mM) of 4-Aminophthalimide in 10 ml of ethanol was refluxed for 3 hours. To the warm solution was added 1 ml of 1M sodium carbonate and the sample was heated for 5 minutes at 100 C., then poured into 300 ml of ice water. The solid was collected, washed with water followed by ether and dried under vacuum at 80 C. to yield 348 mg of 4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-5-ylamino)-6,7-diethoxy-quinoline-3-carbonitrile as a yellow solid: mass spectrum (electrospray, m/e): M+H 402.9, mp=248-251 C.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6288082; (2001); B1;,
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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Nitroindolin-2-one

The derivatives 1 -5 were synthesized following the synthetic procedure reported in scheme 1 of Figure 1 . The 5-nitro-1 ,3-dihydro-2/-/-indol-2-one commercial compound was reduced to the corresponding 5-amino-1 ,3-dihydro-2H-indol-2-one by means of catalytic hydrogenation using Pd/C as a catalyst. The subsequent reaction with the chloro acetyl chloride provided 2-chloro-/V-(2-oxo-2,3-dihydro-1 /-/-indol-5-yl)acetamide which was condensed with the appropriate amine derivative to provide, respectively, 2-[(6,7-dimethoxy-3,4-dihydroisoquinol-2-(1 H)-yl)]-N-(2-oxo-2,3- dihydro-1 H-indol-5-yl)acetamide and 2-[(3,4-dimethoxybenzyl)amino]-/V-(2-oxo- 2,3-dihydro-1 /-/-indol-5-yl)acetamide. Lastly, condensation of the appropriate aromatic carbaldehyde in the presence of pyrrolidine provided the desired products 1 -5.

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:
Patent; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; RAPPOSELLI, Simona; MARTINI, Claudia; CALDERONE, Vincenzo; PURICELLI, Guido; (30 pag.)WO2016/55454; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3676-85-5, name is 5-Aminoisoindoline-1,3-dione, 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. Computed Properties of C8H6N2O2

Example 88 N-(2,4-Dichlorobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (162 mg, 0.59 mmol, 1.2 eq) and triethylamine (60 mg, 0.59 mmol, 1.2 eq) were added to a solution of 2,4-dichlorophenylacetic acid (101 mg, 0.49 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (80 mg, 0.49 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate. The resultant crystal was washed with a chloroform/methanol solution to give the title compound as a crystal (9 mg, 5.0%). MS m/z: 363, 365 1H-NMR delta: 4.37 (2H, d, J = 4.88 Hz), 6.99 (1H, t, J= 5.22 Hz), 7.38 – 7.44 (2H, m), 7.57 – 7.63 (2H, m), 7.68 (1H, d, J = 8.29 Hz), 8.01 (1H, s), 9.46 (1H, s), 11.08 (1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H7NO2

3. Add N-methylphthalimide 19.3g (119.9mmol) and 40mL of 98% sulfuric acid in a 100mL round bottom flask, stir.After the solid was completely dissolved, 18.8 g (65.7 mmol) of dibromohydantoin was added, and the mixture was immediately sealed, and the reaction was further stirred at room temperature for 6 hours.The resulting clear reaction mixture was then poured into 200 mL of ice water.A large amount of white precipitate was precipitated immediately, suction filtered, and washed with deionized water until the filtrate was neutral.Vacuum drying to constant weight,28.2 g of 4-bromo-N-methylphthalimide as a white solid were obtained in a yield of 98.4%.

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 550-44-7.

Reference:
Patent; Shaanxi Normal University; Hanyin Hanyin Middle School; Lv Jiagen; Zhang Shenghai; Cui Hongbo; Gu Min; Zhang Yanling; Li Yintao; Wu Zhaoyi; Liao Ting; (11 pag.)CN108727277; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 435273-55-5, name is 4-Bromo-2-methylisoindolin-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 435273-55-5, HPLC of Formula: C9H8BrNO

; 4-Bromo-2-methylisoindolin-l-one (60 mg, 0.26 mmol) obtained in Step3, 2-formylphenylboronic acid (48 mg, 0.32 mmol), tetrakis(triphenylphosphine)palladium (12 mg, 0.01 mmol) and cesium carbonate (259 mg, 0.80 mmol) were dissolved in a 1 mi ethanol-2 mi toluene mixture and placed in a vessel. The vessel was sealed using aseptum, and heated for 10 min at 150C in a microwave reactor and cooled to room temperature. The reaction mixture was filtered through a cellite column while washing with ethyl acetate, and the solvent was evaporated under a reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 5-methyldibenzoindol-4(5H)-one (62 mg (99%)).1H NMR (300 MHz, CDCl3) delta 8.62-8.51 (m, 2H), 8.12-8.08 (m, IH), 7.90-7.80 (m, 2H), 7.65-7.54 (m, 2H), 7.10 (s, IH), 3.52 (s, 3H).

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; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/51417; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7477-63-6, 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 7477-63-6 as follows.

General procedure: To a pyrex reaction vessel containing a solution of isatin 1a (147 mg, 1.0 mmoL) and NaAuCl4.2H2O (7.95 mg, 2 molpercent) in EtOH (1 mL) was added 4-hydroxycoumarin 2 (324 mg, 2.0 mmoL). The resulting mixture was stirred at 40 °C for 15 min under microwave irradiation (power level of 200 W). After completion of the reaction as evidenced by TLC, the mixture was cooled to room temperature and poured into ice-cold water (10 mL). The solid obtained was collected by filtration and washed with copious amount of cold water and dried under vacuum at 40 oC for 15 min to afford 251 mg of analytically pure product 3a.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Parthasarathy; Praveen, Chandrasekar; Jeyaveeran; Prince; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4310 – 4317;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2518-24-3, 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. 2518-24-3, name is 4-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 66 4-[N’-(1,7-Dioxo-2,3,6,7-tetrahydro-1H-2,6-diaza-as-indacen-8-ylidene)-hydrazino]-N-methyl-benzenesulfonamide (Z-isomer) A solution of 16.2 g (100 mmol) of 6-aminophthalimide, 9.6 g (100 mmol) of methanesulfonic acid, and 4.0 g of 10% Pd/C in 140 mL of TFA was hydrogenated overnight at 50 psi. The catalyst was filtered off and and the filtrate concentrated on a rotary evaporator. The residue was diluted with 70 mL of ice water, adjusted to pH 8 with K2CO3, and chilled in an ice bath. The resulting solid was filtered to give 6.7 g of a 5:4 ratio of 5-amino:6-amino lactam isomers. Recrystallization from hot ethanol/water afforded 1.45 g of undesired isomer. The filtrate was preabsorbed onto silica gel and chromatographed with TEA:MeOH:methylene chloride (1:2:47). The resulting solid was slurried in methylene chloride/MeOH and filtered to afford a low yield of 5-amino-2,3-dihydro-isoindol-1-one: 1H NMR (DMSO-d6): delta4.13 (s, 2H), 5.67 (s, 2H), 6.55 (dd, J=8.7, 1.9 Hz, 1H), 6.55 (d, J=1.9 Hz, 1H), 7.25 (d, J=8.7 Hz, 1H), 7.83 (s, 1H); APCI-MS m/z 149 (M+H)+.

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, 4-Aminoisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SmithKline Beecham Corporation; US6369086; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a cold (0 C.) solution of N-(chloromethyl)phthalimide (40.0 g, 205.0 mmol) in acetone (400 mL) there is added, in successive portions, potassium O-ethylxanthate (36.1 g, 225.0 mmol). The reaction mixture is stirred at 0 C. for 30 minutes and then the solvent is evaporated off. The residue thereby obtained is taken up in water. The aqueous phase is extracted with dichloromethane, whilst the organic phases are dried over MgSO4 and concentrated under reduced pressure. The residue thereby obtained is recrystallised from a mixture of ethyl acetate and petroleum ether to yield the title product in a yield of 74%. 1H NMR (delta, ppm) 7.90-7.84 (m, 2H, CH-2), 7.77-7.72 (m, 2H, CH-1), 5.33 (s, 2H, (CDCl3, 400 MHz) CH2-5), 4.68 (q, 2H, J=7.1 Hz, CH2-7), 1.46 (t, 3H, J=7.1 Hz, CH3-8).

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; Zard, Samir; Sire, Beatrice; Boumediene, Mehdi; US2013/289308; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem