Author: Jessica.F

Related Products of 100510-65-4,Some common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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.

EXAMPLE A 6-Benzoylamino-2,3-dihydro-3,3-dimethyl-(1H)-indolin-2-one To a suspension of 5.28 g. (0.03 mole) 6-amino2,3-dihydro-3,3-dimethyl-(1H)-indolin-2-one and 4.6 ml. triethylamine in 50 ml. anhydrous dichloromethane is added dropwise at 0 C., within the course of 15 minutes, 4.36 g. (0.031 mole) benzoyl chloride, followed by stirring for 1 hour at ambient temperature. The reaction mixture is then mixed with 200 ml. ice water and the precipitate is filtered off with suction, washed with water and recrystallized from methanol. Yield 7.8 g. (93% of theory); m.p. 251-254 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Amino-3,3-dimethylindolin-2-one, its application will become more common.

Reference:
Patent; Boehringer Mannheim GmbH; US4985448; (1991); A;,
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. 769965-95-9, name is 5′-Fluorospiro[cyclopropane-1,3′-indolin]-2′-one, A new synthetic method of this compound is introduced below., Recommanded Product: 769965-95-9

A mixture of {5-chloro-1-[2-(methylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}methyl methanesulfonate (183 mg, 0.50 mmol), cesium carbonate (325 mg, 1.0 mmol) and 5′-fluorospiro[cyclopropane-1,3′-indol]-2′(1’H)-one (79 mg, 0.50 mmol) in N,N-dimethylformamide (5 mL) was heated with stirring at 60C for 30 minutes. The resulting mixture was purified by preparative HPLC to afford the title product.

The synthetic route of 769965-95-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; GAO, Lu; GUO, Lei; HUANG, Mengwei; LIANG, Chungen; WANG, Baoxia; WANG, Lisha; WU, Guolong; YUN, Hongying; ZHANG, Weixing; ZHENG, Xiufang; ZHU, Wei; WO2014/184163; (2014); A1;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-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 99365-40-9, Recommanded Product: 99365-40-9

Di-tert-butyl dicarbonate (4.63 g, 21.2 mmol) and sodium hydrogen carbonate (10.7 g, 127 mmol) were added to a stirred solution of 6-bromoindolin-2-one (preparation 1, 3.0 g, 14.2 mmol) in tetrahydrofuran (150 mL) and the mixture was heated to reflux. After 3 hours the mixture was cooled and filtered and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (10:1 hexanes/ethyl acetate) gave the title compound (3.58 g, 81%) as a white solid. LRMS (m/z): 312/314 (M+1)+. 1H-NMR delta (CDCl3): 1.65 (s, 9H), 3.66 (s, 2H), 7.10(d, 1H), 7.27 (d, 1H), 8.03 (s, 1H).

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, 6-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 21544-81-0, The chemical industry reduces the impact on the environment during synthesis 21544-81-0, name is 4,6-Dimethoxyindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

EXAMPLE 2 4,6-dimethoxyanthranilic acid To a heated mixture (in an oversized flask) of 13 g (63 mmol) 4,6-dimethoxyindole-2,3-dione prepared in Example 1 and 108 ml of 33% NaOH solution was carefully added 20 ml of a 30% solution of H2O2. A vigorous exothermic reaction occurs. After all H2O2 was added, the reaction mixture was maintained at 100 C. for an additional 10 min. The pH of the solution was brought to 8 with concentrated HCl and acidified to pH 5-6 with acetic acid. The solid was filtered, washed with water and dried to yield 6.2 g of 4,6-dimethoxyanthranilic acid as a pale brown solid (50% yield). C9H11NO4=197.19 g/mol; HPLC purity=100%; ESI-LC/MS (M+H)+=198.: MP:120-125 C.; 1H NMR (400 MHz, DMSO-d6): delta5.94 (d, J=1.76 Hz, 1H), 5.79 (d, J=1.76 Hz, 1H), 3.75 (s, 3H), 3.71 (s, 3H).

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, 4,6-Dimethoxyindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gungor, Timur; Corte, James R.; US2003/220227; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

141452-01-9, name is Methyl indoline-5-carboxylate, 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. SDS of cas: 141452-01-9

A 50 ml. RBF was charged with methyl, indoline-5-carboxylate, (2 g, 11 .3 mmol), DCM (20 ml_, 0.6 M), diisopropylethylamine (5.83 g, 45.1 mmol, 4.0 equiv.), and the stirred reaction mixture was then treated dropwise with benzyl chloroformate (5.78 g, 33.9 mmol, 3.0 equiv.). The reaction mixture was stirred for 24 h at RT and then concentrated under reduced pressure. The crude material was purified on silica gel (40 g Si02, 0-100% EtOAc-hexanes) to afford 0-1-benzyl-0-5-methylindoline-1 ,5- dicarboxylate (2.50 g, 3.52 theoretical, 71.0%). 1 H NMR (CDCI3): d 7.79-7.75 (m, 3H), 7.40-7.20 (m, 5H), 5.20 (s, 2H), 4.00 (t, 2H), 3.81 (s, 3H), 3.14 (t, 2H); LCMS: 312 (M+1 ).

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLLABORATIVE MEDICINAL DEVELOPMENT PTY. LTD.; WARNER, John, C.; BALDINO, Carmen; MUOLLO, Lauren; ROSENFELD, Craig; (109 pag.)WO2019/106434; (2019); A1;,
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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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., COA of Formula: C8H9N

To ketone 24 (43 mg, 0.15 mmol) in anhydrous THF/CH2Cl2 (1.5 ml/1.5 mL) is added isoindoline (25 muL, 0.22 mmol) and glacial acidic acid (3 muL) and triacetoxyl sodium borohydride (98 mg, 0.44 mmol). The mixture is stirred for 2 h and, quenched with saturated sodium bicarbonate, and extracted with CH2Cl2. The organic phase is dried, rotavaped, and was subjected to HPLC purification (aetonitrile-water-0.1% TFA) to give the title compound as a TFA salt (67 mg, 89%).1H-NMR (400 MHz, CDCl3) delta=2.2 (4H, m), 2.3 (3H, s), 2.4 (3H, s), 3.2 (2H, m), 3.6 (1H, m), 3.8 (2H, m), 4.5 (4H, bs), 5.1 (2H, bs), 7.3 (9H, m).HR MS (m/z, MH+) meas. 399.2547.

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; Novartis AG; US2010/41663; (2010); A1;,
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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, A new synthetic method of this compound is introduced below., Quality Control of Potassium 1,3-dioxoisoindolin-2-ide

General procedure: A 500 mL round-bottom flask was charged with4.63 g (0.025 mol) Phthalimide potassium salt, dissolve in 120 mL Anhydrousacetone. 6.9 g (0.05 mol) potassium carbonate and 11.75 g (0.0625 mol) 1,2-Dibromoethanewas added. The solution was heated to reflux for 8 h. The stirring mixture wasallowed to cool, and then was filtered. The solids were washed with 50 mL ofacetone, followed by 50 mL of EtOAc. The filtrate and the washer liquid werepooled and concentrated in a rotary evaporator, then purified by flashchromatography on SiO2 (gradient, 1:6 to 1:4 petroleum ether:EtOAc)to obtain 5.2 g (81.8%) of N-(2-Bromoethyl) phthalimideas a white solid.

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; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, 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. Safety of N-Phthaloylglycine

To 10.25 g of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid dissolved in 50 ml of dichloromethane are added, at room temperature, 4.6 ml of oxalyl chloride and 2 drops of DMF, and the mixture is left for 18 hours at room temperature. The resulting mixture is evaporated to dryness to give 11 g of the expected product.

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

Reference:
Patent; SANOFI-AVENTIS; US2007/185136; (2007); A1;,
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. 199328-10-4, name is Methyl Oxindole-5-carboxylate, A new synthetic method of this compound is introduced below., name: Methyl Oxindole-5-carboxylate

Into a 50-mL round-bottom flask was placed methyl 2-oxo-2,3-dihydro-1H- indole-5-carboxylate (800 mg, 4.18 mmol, 1.00 equiv) and methanol (10 mL). This was followed by the addition of a solution of NaOH (670 mg, 16.75 mmol, 4.00 equiv) in water (10 mL) dropwise with stirring at 0oC. The resulting solution was stirred for 14 h at 20oC. The mixture was then concentrated under vacuum and the residue taken up in 20 mL of H2O. This was washed with 2×5 mL of dichloromethane. The pH was adjusted to 4 with hydrochloric acid (1 N) and extracted with 5×50 mL of ethyl acetate and the organic layers combined. Concentration resulted in 592 mg (80%) of 2-oxo-2,3-dihydro- 1H-indole-5-carboxylic acid as a yellow solid

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; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 56341-37-8, 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. 56341-37-8 name is 6-Chlorooxindole, 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 3Preparation of 6-chloro-5-(chloroacetyl) oxindole :Charged with 500 ml of ethylene dichloride and A1C13 (250gm) in a 3 litre there-neck flask under nitrogen atmosphere at 25 to 30C. Add 84.19 gm of chloroacetyl chloride slowly at RT controlling the exotherm and stirred for 30 minutes.Contents are further added with 100 gm of 6- chloro-oxindoie at 35-37C in an hour. Stirring is continued at 35-37C for 10-12 hrs.Cool gradually to 0 to 5C and pour into ice, and water under stirring over 30 minutes. Stir for 30 minutes, remove ethylene dichloride by distlation under vacuum, cool the mass and filter off the product wash with water till it is neutral. Purify the product using 1,4- dioxane if required.

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

Reference:
Patent; ARCH PHARMALABS LIMITED; GHOGARE, Bhausaheb Nana; DESHPANDE, Uday K.; PAI, Ganesh Gurpur; MANDAL, Arun Kanti; CHARANJIT, Sehgal; NEHA, Dixit Akshaya; WO2012/20424; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem