Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 6341-92-0, name is 6-Chloroisatin, 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 6341-92-0, Recommanded Product: 6-Chloroisatin

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, mp 196-198 C.

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Reference:
Patent; Pfizer Inc.; US4658037; (1987); A;; ; Patent; Pfizer Inc.; US4652658; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. Application In Synthesis of 1-Acetylindolin-3-one

General procedure: To 5-bromo-N-acetyl indoxyl (0.018 mole), Titanium isopropoxide (0.027 mole) was added under nitrogen atmosphere. The mass was stirred for 30 min at room temperature. N-Methyl piperazine (0.02 mole) was added neat to the above complex. The reaction mass was further at room temperature for 5 hr. Absolute ethanol (20 mL) was added to the thick slurry mass followed by the addition of sodium triacetoxyborohydride (0.036 mole). After completion of the reaction (TLC), the reaction mass was diluted with water (100 mL) and the precipitated titanium complex was removed by filtration. The solid on the filter was washed with ethyl acetate till colourless filtrate was obtained. The filtrate was basified with aqueous ammonia whereby compound went into organic layer. The organic layer was separated, washed with brine solution (1 x 50 mL) and dried over anhydrous magnesium sulfate. Solvent was removed under reduced pressure and the residual mass was purified by flash chromatography over silica gel using 70 % ethylacetate in n-hexane to obtain the title compound in 70% yield.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirogi, Ramakrishna V.S.; Deshpande, Amol D.; Kambhampati, Ramasastri; Badange, Rajesh Kumar; Kota, Laxman; Daulatabad, Anand V.; Shinde, Anil K.; Ahmad, Ishtiyaque; Kandikere, Vishwottam; Jayarajan, Pradeep; Dubey; Bioorganic and Medicinal Chemistry Letters; vol. 21; 1; (2011); p. 346 – 349;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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.

EXAMPLE 45 To a suspension of 1.76 g of 5-carboxyoxindol in 200 ml of methylene chloride was added 2 ml of pyridine. After completion of addition, to the suspension was added dropwise 1.4 g of thionyl chloride with stirring held at 0 to 20 C. After completion of addition, the mixture was stirred at the same temperature for 1 hour, and a solution of 1.74 g of benzylpiperazine in 10 ml of methylene chloride was added dropwise thereto. The mixture was then stirred for 4 hours at room temperature. The reaction mixture was thoroughly washed with an aqueous potassium carbonate solution, then washed with water, and dilute hydrochloric acid, dried over sodium sulfate, and the solvent was distilled off. The residue was isolated and purified by silica-gel column chromatography [silica-gel: WAKO C-200, eluent: chloroform:methanol (V/V)=20:1] followed by recrystallization from isopropyl alcohol to give 298 mg of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol. m.p.: 151-153 C.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
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 64483-69-8 as follows. category: indolines-derivatives

General procedure: Indolinone 1 (1000 mg, 52.3 mmol) was suspended in acetic anhydride (10 mL) and refluxed at 130 C for 8 h. The reaction mixture was allowed to cool to 50 C and (triethoxymethyl)benzene(2930 mg, 131 mmol) was added. The resulting reaction mixture was stirred at 120 C for 6 h. Then, volatiles were removed in vacuo and petroleum ether was added to the obtained residue. After triturating for 15 min, the separated solids were filtered and washed with petroleum ether and then dried under vacuum to afford974 mg (51%) of title compound.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Edupuganti, Ramakrishna; Taliaferro, Juliana M.; Wang, Qiantao; Xie, Xuemei; Cho, Eun Jeong; Vidhu, Fnu; Ren, Pengyu; Anslyn, Eric V.; Bartholomeusz, Chandra; Dalby, Kevin N.; Bioorganic and Medicinal Chemistry; vol. 25; 9; (2017); p. 2609 – 2616;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 16800-68-3, A common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

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; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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 39755-95-8 as follows. Safety of 5-Methoxyisatin

5-Hydroxy isatin (2). To a stirred solution of 5-methoxy isatin (1) (10.0 g, 56.5 rnmol, 1.0 equiv) in CH2CI2 (40 mL) at 0 C, BBr3 (36.8 g, 147 mmol, 2.6 equiv) was added dropwise over 2 h under vigorous stirring at 0 C. Upon completion of addition, the ice bath was removed and the reaction mixture was stirred for another 1 h at room temperature and was diluted with CH2CI2 (500 mL), cooled to 0 C, quenched by careful sequential addition of solid NaHC03 (37 g), and cold (0-5 C) H20 (60 mL) (CA UTION, HBr gas). The resulting mixture was washed with brine (50 mL), and the combined aqueous phases were extracted with CH2CI2 (50 mL). The combined organic phases were concentrated and the residue was recrystalhzed from glacial acetic acid to yield isatin 2 as a dark red solid (8.8 g, 54 mmol, 95% yield). R = 0.31 (silica gel, CH2Cl2:EtOAc 1 : 1); IR (film) vmax = 3278, 1720, 1614, 1477, 1291, 1194, 881, 822, 800 cm”1; FontWeight=”Bold” FontSize=”10″ H NMR (500 MHz, DMSO): delta = 10.73 (s, 1 H), 9.52 (br, 1 H), 7.00 (dd, J = 8.5, 2.6 Hz, 1 H), 6.83 (d, J = 2.6 Hz, 1 H), 6.74 (d, J = 8.3 Hz, 1 H) ppm; 1 C NMR (125 MHz, CDC13): delta = 184.9, 159.5, 153.2, 143.1, 125.1, 118.2, 113.1, 110.5, 105.1 ppm; HRMS (ESI-TOF): calcd for C8H6N03+ [M+H+] : 164.0342, found 164.0344.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WILLIAM MARSH RICE UNIVERSITY; BRISTOL-MYERS SQUIBB COMPANY; THE SCRIPPS RESEARCH INSTITUTE; NICOLAOU, Kyriacos, C.; LU, Min; MANDAL, Debashis; GANGWAR, Sanjeev; CHOWDARI, Naidu, S.; POUDEL, Yam, B.; WO2015/23879; (2015); 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. 6341-92-0, name is 6-Chloroisatin, A new synthetic method of this compound is introduced below., Computed Properties of C8H4ClNO2

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 mol%) 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.

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

Application of 1914-02-9, A common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, 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 suspension of NaHC03 (5.41 g, 64.39 mmol) and 3,3-dimethylindoline (0.79 g, 5.37 mmol) in DCM (10 mL) was added acetyl chloride (0.76 mL, 10.73 mmol) dropwise at 0 C. The reaction was stirred at rt for 2 h, then filtered. The filtrate was concentrated in vacuo to give the title compound as a white solid (0.99 g, 97.1%). MS (ESI, pos. ion) m/z: 190 [M + H]+; NMR (CDCI3) delta (ppm): 8.11 (d, 1H), 7.13 (t, 1H), 7.06 (d, 1H), 6.97 (t, 1H), 3.70 (s, 2H), 2.15 (s, 3H), 1.29 (s, 6H).

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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: 19155-24-9

A solution of 3,3-dimethylindolin-2-one (1.5 g, 9.31 mmol)Was dissolved in tetrahydrofuran (90 mL)The solution was cooled to 0 C,To this was added borane-tetrahydrofuran (37.3 mL, 37.22 mmol).The reaction solution was refluxed at 87 C overnight,Cooled to room temperature and quenched with methanol (10 mL).The mixture was further refluxed at 85 C for 2 hours, after which it was concentrated under reduced pressure.The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 20/1)The title compound was obtained as a yellow oil (0.87 g, 63.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19155-24-9, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 21857-45-4, 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 21857-45-4 as follows.

To a solution of 5-methoxyindoline (180 mg, 1.21 mmol) in 3.6 mL of acetic acid was added 3,3-dimethylbutylaldehyde (0.18 mL, 1.4 mmol) and sodium cyanoborohydride (190 mg, 3.0 mmol) at room temperature, successively. After the reaction mixture was stirred for 2 h, the reaction mixture was basified by saturated NaHCO3 aqueous solution and the solution was extracted with ethyl acetate (20 mL). The extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 90/10) to obtain 5-methoxy-1-(3,3-dimethylbutyl)indoline (74.6 mg, 26%).

According to the analysis of related databases, 21857-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; KYOTO UNIVERSITY; US2011/294850; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem