Category: indolines-derivatives

Related Products of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-1,3-dione, 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.

Heck reaction of 4-Bromophthalic imide with 1,7-Octadien (Heck condition) 1 g 4-Bromophthalic imide (6.167 mmol), a two-fold excess 1,7-Octadien (12.33 mmol) and the catalysator system were solved in 50 ml DMF. The catalysator system consisted of Palladiumacetate (5 mol-% to Imide: 0.31 mmol), 0.92 mmol Triphenylphosphane and 6.17 mmol Triethylamin. The solution has been heated for 24 h at 150 C (Control of reaction progress via thin layer chromatography with CH2Cl2: n-Hexane [5:1]). From the resulting dark brown solution the solvent was removed by reduced pressure. The obtained viscous brown raw product was solved with 80 ml CH2Cl2 and washed three times (3 x 200 ml) with a saturated H2O/NaCl solution. After that the CH2Cl2-phase was dried with MgSO4 and the solvent was removed by reduced pressure. The viscous brown product (1) was dried under constant vacuum.Yield : quant. IR : v 1772, 1717 (s, Imide) cm-1 MS / ESI : 401.14972 m/z (M+H+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; DENTSPLY DETREY GmbH; E, Klee, Joachim; Retzmann, Nils; Ritter, Helmut; Szillat, Florian; EP2759289; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7699-18-5, These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-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.

General procedure: A suspension of indolinone (0.3mmol), aldehyde (0.3mmol) and pyridine (30muL) in methanol (1mL) were heated under microwave irradiation at 100 C for 30 minutes. The reaction mixture was cooled to room temperature and the resulting precipitate was removed by filtration, carefully washed with methanol and dried in vacuo. When no precipitate was observed methanol was removed under vacuum and the residue was purified by silica gel chromatography to give the desired product.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H4ClNO2

To a solution of 5-chloro-isoindole-l,3-dione (5.0 g, 27.5 mmol) in DCM (200 mL) was added ethylmagnesium chloride (2 M in THF, 41.3 mL) dropwise at 0 C. After the addition, the mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regioisomers (5.82 g, 100%). MS: 212.0 (M+H+).

According to the analysis of related databases, 7147-90-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 391-12-8, name is 7-(Trifluoromethyl)isatin, molecular formula is C9H4F3NO2, 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. Recommanded Product: 391-12-8

EXAMPLE 6 20 parts of a 30 percent strength by weight solution of sodium methylate in methanol are added to 21.5 parts of 7-trifluoromethylisatin in 300 parts of methanol at 0° C., resulting in a violet solution. 8 parts of a 50 percent strength by weight hydrogen peroxide solution are then added at 0° C., after which the mixture is stirred for one hour at room temperature. The reddish solution is concentrated, water is added, the pH is brought to 8 with hydrochloric acid and the batch is extracted by shaking with methylene chloride. After concentrating the methylene chloride phase, 16.2 parts (74percent of theory) of methyl 3-trifluoromethylanthranilate are obtained. H1 –NMR (CDCl3): delta=3.8 ppm (s), 6.4 (s, N–H2), 6.6 (t), 7.5 (d) and 7.95 (d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 391-12-8, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US4310677; (1982); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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 solution of 6-nitroindoline (a) (3 g, 18.3 mmol) in DCM (30mL) was added di-tert-butyl dicarbonate (4.8 g, 22 mmol) and TEA (3.7 g, 36.6 mmol). The solution was stirred for 5 h at room temperature then washed with water and brine. The organic layer was dried, filtered and concentrated. Silica gel column chromatography provided tert-butyl 6-nitroindoline-l-carboxylate (b) as a white solid (2.4 g, 50%).

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

Reference:
Patent; ISOCURE BIOSCIENCES INC.; ZHANG, Tinghu; CHE, Jianwei; (118 pag.)WO2018/71404; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1127-59-9, name is 7-Methylindoline-2,3-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. category: indolines-derivatives

Preparation of 7-bromomethylisatin The 7-methylisatin (16.1 g, 0.1 mole) is suspended in dichloroethane (2000 ml) and the suspension is heated and irradiated with a high intensity light source to the reflux point. Bromine (24.3 g, 0.15 mole) is added dropwise over a one hour period. The solution is filtered hot and concentrated at reduced pressure to yield the product as an orange solid after washing with anhydrous diethyl ether. The product is purified using flash chromatography on silica (elution with 24:1 dichloromethane:diethyl ether) to afford after drying (at 60° C. at 0.1 mm); 7-bromomethylisatin, mp 199°-200° C. dec.

The synthetic route of 1127-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4530929; (1985); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-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. Quality Control of 5-Methylindolin-2-one

General procedure: To a solution of appropriate oxindole (8a-e, 0.3 mmol) in ethanol (3 mL) was addedcorresponding aldehyde (12a-h, 0.32 mmol) and a catalytic amount of piperidine. The reactionmixture was stirred at reflux for 6-12 h (monitored by TLC). After cooling, the precipitate wasfiltered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(4′-(aminoalkoxy)-3′-methoxybenzylidene)indolin-2-one title compounds of formula (5a-t) as yellow/brown/orangesolids in moderate to excellent yields.

The synthetic route of 5-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6941-75-9, The chemical industry reduces the impact on the environment during synthesis 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Under a nitrogen atmosphere, at 0 C., to a solution of WX042-1 (5.00 g, 22.12 mmol) in tetrahydrofuran (50.00 mL) was added borane dimethyl sulfide (10 M, 11.06 mL) dropwise, and the system was stirred at 70 C. for 16 hours. After the reaction was complete, at 0 C. to the system was added 100 mL methanol to quench the reaction system. After concentration under reduced pressure, the residue was purified by column chromatography (dichloromethane:methanol=20:1) to afford Compound WX042-2 (1.00 g, 22.16% yield, 97.1% purity), white solid. 1H NMR (400 MHz, DMSO-d6) delta 7.43 (s, 1H), 7.40-7.34 (m, 2H), 7.11 (d, J=8.5 Hz, 1H), 4.48 (d, J=16.6 Hz, 4H).

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

Reference:
Patent; Medshine Discovery Inc.; He, Haiying; Jiang, Zhigan; Shi, Weihua; Xia, Jianhua; Li, Jian; Chen, Shuhui; US2019/375744; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, 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. name: 3-Nitrophthalimide

3-Nitrophthalimide (5 g) and hydroxylamine sulfate powder (11 g) were sequentially added to isopropanol (90 mL).Stir the reaction mixture.A solution of potassium hydroxide (6 g) in water (5 ml) was added in one portion.Get a red liquid.The temperature of the reaction solution was slowly raised to 40 C, the solution was stirred for 30 minutes, filtered,Recrystallization twice with water, dried at 80 to give 1.4g yellow needle crystal,After vacuum drying at 120 C, 1.12 g (24% yield) of yellow powder was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 603-62-3, its application will become more common.

Reference:
Patent; Shanghai Zaiqi Biological Co., Ltd.; Wang Zhiguo; Song Yanhong; Ma Xiujuan; Tian Beibei; Li Shijiang; Li Chao; Zhang Xin; Li Tao; (7 pag.)CN107474007; (2017); A;,
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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-1-methylindoline-2,3-dione

General procedure: N-substituted isatin (3a-g) (0.9 mmol) and tryptamine (4) (1 mmol) in EtOH (5mL) in the presence of (0.2 mL) glacial acetic acid and 4 A molecular sieve were stirred at RT for 24 hours. The precipitate was removed by filtration and the filtrate was concentrated and purified by column chromatography (silica gel, hexane/EtOAc (2:1) to give compounds 5a-g.

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 2058-72-2.

Reference:
Article; Phutdhawong, Weerachai; Rattanopas, Sopita; Sirirak, Jitnapa; Taechowisan, Thongchai; Phutdhawong, Waya S.; Oriental Journal of Chemistry; vol. 35; 2; (2019); p. 723 – 731;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem