Tag: M.W=100-200

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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Safety of 2-Oxoindoline-5-carboxylic Acid

General procedure: Aldehydes (1-5) (0.2 mmol) and oxindoles (7-11) (0.2 mmol) were dissolved in alcohol MeOH, EtOH, or tert-BuOH (1.5 ml). 3 droplets of piperidine were added to the solvents and the reaction mixture was stirred in a sealed vial at 60 – 70 C for 2 – 8 hours.

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; 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;,
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Reference of 22190-33-6,Some common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2×). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171308; (2014); A1;,
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Synthetic Route of 56341-39-0, 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. 56341-39-0 name is 6-Fluoroindolin-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.

EXAMPLE 14 A solution of 6-fluorooxindole (227 mg, 1.5 mmol), (prepared according to Synthesis 1993, 51), in THF (3 ml) was added dropwise under nitrogen to sodium hydride (42 mg, 1.75 mmol, pre-washed with hexane). After stirring the resulting mixture for 20 minutes at ambient temperature, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (169 mg, 0.5 mmol), (prepared as described for the starting material in Example 5), was added as a solid, followed by DMF (3 ml). The mixture was then heated at 75 C. for 1 hour, allowed to cool and the solvent removed by evaporation The mixture was partitioned between water and ether. The aqueous layer was separated and adjusted to pH8 with 2M hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with brine, dried and volatiles removed by evaporation. The residue was triturated with ether and collected by filtration. This solid was dissolved in methylene chloride/methanol, a 5M solution of hydrogen chloride in isopropanol (0.5 ml) was added and the volatiles removed by evaporation. The resulting solid was collected by filtration, washed with ether and dried under vacuum to give 4-(6-fluorooxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline hydrochloride (198 mg, 81%) as a yellow solid. m.p..195-200 C. 1H NMR Spectrum: (DMSOd6, CF3CO2D) 2.25-2.4(m, 2H); 3.05-3.2(m, 2H); 3.25-3.35(m, 2H); 3.52(d, 2H); 3.72-3.85(m, 2H); 3.9(s, 3H); 4.05(d, 2H); 4.3(t, 2H); 6.8-6.9(m, 2H); 7.32(s, 1H); 7.62-7.7(m, 1H); 7.78(s, 1H); 8.7-8.8(m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Fluoroindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
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19727-83-4, name is 6-Nitroindoline, 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 6-Nitroindoline

To a stirred solution of 6-nitroindoline (8.0 g, 48.8 mmol) in DCM (50 ml_) was added pyridine (9.9 ml_, 122 mmol), (Boc)2O (10.6g, 48.6 mmol) and catalytic DMAP. EPO The mixture was stirred overnight. Reaction was washed with brine, and the organic layer was dried (Na2SO4), filtered and concentrated. Chromatography (20% EtOAc/hexanes) provided 1-Boc-6-nitroindoline (10 g, 78%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2007/24944; (2007); A1;,
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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;,
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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

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;,
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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. 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;,
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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;,
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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. 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