Category: indolines-derivatives

Related Products of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step A-Preparation of 1-(6-nitroindolinyl)-2-piperidylethan-1-one 6-Nitroindoline (2.5 g) was dissolved in 200 mL of CH2Cl2, followed by DIEA (2.5 g).The mixture was cooled down to 0 C. in ice bath.chloroacetyl chloride (1.7 g) in 20 mL CH2Cl2 was added dropwise to the mixture over 10 min and the mixture was stirred at RT overnight.The mixture was extracted once with saturated NaHCO3 solution and once with brine, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 3:2 hexane:EtOAc to afford a yellow oil (1.4 g) which was added to piperidine (5 mL), followed by NaI (100 mg).The mixture was heated at 70 C. overnight then concentrated in vacuo and extracted between EtOAc and saturated NaHCO3 solution, the organic layer was washed with brine, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 9:1 EtOAc:MeOH to afford a yellow oil. MS: 290 (M+1). Calc’d. for C15H19N3O3-289.33.

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-Nitroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 15861-30-0, A common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, molecular formula is C9H9NO2, 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.

Reference Example 1 Synthesis of 1-carbobenzoxy-5-carboxyindoline To a mixture of water (20 ml) and diethyl ether (20 ml) were added 5-carboxyindoline (2.0 g) and sodium hydroxide (0.6 g), and then, under ice-water cooling, carbobenzoxy chloride (2.59 g) and water (10 ml) containing sodium hydroxide (2.1 g) were added to the mixture thereto alternatively. The mixture was stirred at room temperature for 2 hours. The reaction mixture was made acidic with 2N-hydrochloric acid and precipitated crystals were collected by filtration. Precipitates were washed with ether and air-dried to obtain the title compound (2.8 g). 1 H-NMR (DMSO-d6, delta): 3.10 (2H, t, J=8 Hz), 4.03 (2H, t, J=8 Hz), 5.23 (2H, s), 7.2-8.0 (8H, m). mp; 194-196 C.

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; US5354753; (1994); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

337536-15-9, name is 4-Bromoisoindolin-1-one, 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 C8H6BrNO

Step 4: Preparation of 4-bromo-7-nitroisoindolin-1-one (5) To a solution of 4-bromoisoindolin-1-one 4 (3.0 g, 14.1 mmol) in conc. H2SO4 (6 mL) at 0 C. was added dropwise a solution of conc. HNO3 (1 mL) in conc. H2SO4 (6 mL) The resulting mixture was then stirred at room temperature overnight, then poured over ice, and filtered. The filter cake was washed with water, MTBE, dried in vacuo to give the title product 5 (3.0 g). 1H NMR (400 MHz, DMSO-d6) delta 9.17 (s, 1H), 8.06-8.04 (d, J=8.4 Hz, 1H), 7.89-7.87 (d, J=8.4 Hz, 1H), 4.39 (s, 2H).

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GREEN CROSS CORPORATION; CHOI, Soongyu; PARK, Eun-Jung; SEO, Hee Jeong; KONG, Younggyu; SON, Ickhwan; MA, Sang-ho; CHA, Man-Young; KIM, Mi-Soon; PARK, Kisoo; (143 pag.)US2016/311772; (2016); 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(Chloromethyl)isoindoline-1,3-dione

EXAMPLE 42 To a stirred solution containing 15 grams (0.12 mole) of amine, 19.2 grams (0.12 mole) of 25% sodium hydroxide and 250 ml. of acetone there was added dropwise at 5-15 C., 9.2 grams (0.12 mole) of carbon bisulfide. After stirring at 25-30 C. for an hour, 19.6 grams (0.1 mole) of phthalimidomethyl chloride was added in one portion and stirring continued at 25-30 C. for another hour. Thereupon there was added 700 ml. of water and the reaction mixture stirred and cooled to 5 C. The product was isolated as described in Example 41. Phthalimidomethyl 3-azabicyclo[3.2.2]nonane-3- carbodithioate was obtained in 99% yield as a grey solid melting at 139-140 C. after recrystallization from ethyl alcohol/benzene. Analysis gave 7.46% nitrogen and 18.09% sulfur compared to 7.77% nitrogen and 17.79% sulfur calculated for C18 H20 N2 O2 S2.

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 17564-64-6.

Reference:
Patent; Monsanto Company; US4013638; (1977); 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 19727-83-4 as follows. Application In Synthesis of 6-Nitroindoline

Reference Example 58 In 50 ml of methylene chloride was dissolved 2.5 g of 6-nitroindoline, and then 6.37 ml of triethylamine was added thereto. Under ice cooling, 3.51 g of methanesulfonyl chloride was added dropwise, the reaction solution was stirred at room temperature for 3 hours, and then ice-water was added thereto, followed by 1 hour of stirring. The reaction solvent was removed by evaporation under reduced pressure, a 1M aqueous hydrochloric acid solution was added to the residue, and precipitated was filtrated off, whereby 3.52 g of 1-methylsulfonyl-6-nitroindoline was obtained as a brown solid.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Astellas Pharma Inc.; EP1632477; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3, 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.

EXAMPLE 308; 3-(6-Chloro-2-propyl-2H-pyrazolo[3,4-d]pyrimidin-4-yl)-5-methyl-1,3-dihydroindol-2-one; A solution of 5-methyloxindole (147 mg, 1.0 mmol) and compound 105 (231 mg, 1.0 mmol) in 2 mL dry THF and 2 mL dry DMF was cooled to 0 C., and a dispersion of 60% NaH in mineral oil (80 mg, 2.0 mmol) was added. After the hydrogen evolution ceased, the reaction mixture was allowed to warm to rt. The reaction mixture was stirred under N2 for 2 days. The dark yellow homogeneous reaction was quenched with sat. NH4Cl, and a yellow precipitate formed. The precipitate was washed with water, and the product allowed to air dry. The crude product was then suspended in diethyl ether, and the yellow solid recovered by filtration affording g (80%) of the product: mp 275-80 C. 1H NMR (400 MHz, TFA-d): delta 9.68 (s, 1H), 8.41 (br s, 1H), 8.09 (d, J=7.8 Hz, 1H), 8.02(d, J=7.8 Hz, 1H), 5.33(q, J=6.3 Hz, 2 H), 3.30 (s, 3H), 2.97(dq, J=6.3,7.1 Hz), 1.93(t, J=7.1 Hz).

Statistics shows that 5-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 3484-35-3.

Reference:
Patent; Cephalon, Inc.; US2007/281949; (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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., COA of Formula: C9H6ClNO2

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

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; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 239463-85-5, A common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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: 3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H-indol-1-yl}Propyl benzoate(2R, 3R) -mono-tartaric acid salt(Mono-tartaric acid salt of the compound of formula (II)),Potassium carbonate (80 g),And a mixed solvent of acetonitrile and dimethylacetamide (ACN / DMAC = 500 mL / 500 mL) was heated to 80 DEG C,Stir for 30 min. To the reaction mixture were added 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula 3) and 9.70 g of KI,The reaction was carried out at the same temperature for 10 hours.The reaction mixture was cooled to room temperature,And extracted with 1 L of ethyl acetate and 1.5 L of water.The organic layer obtained by layer separation was washed with 1 L of brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing again with 200 mL of ethyl acetate, the solvent was removed by distillation. 400 mL of methanol, 100 mL of water and 20 g of KOH were added to the obtained residue. After the mixture was stirred at room temperature for 10 hours,1 L of ethyl acetate and 1 L of water were added and extracted for 10 minutes.The organic layer obtained by layer separation was washed sequentially with 1 L of saturated aqueous solution and 1 L of saturated brine,After drying over 40 g of anhydrous MgSO4 for 30 minutes,After washing with 200 mL of ethyl acetate,18 g of oxalic acid was added.The reaction mixture was stirred at 50 for 30 minutes, It cooled to room temperature.600 mL of isopropyl ether was added to the reaction mixture,Stirred for 2 hours, and then filtered.The obtained crystals were washed with 200 mL of isopropyl ether,At 40 for 10 hours to give the titled compound as a dried in vacuo to 88 g.The reaction was carried out in the same manner as in Example 1, except that 23.5 g of fumaric acid was used instead of oxalic acid to obtain 92 g of the title compound.Yield: 81%Purity: 99.5%Impurities (dimer): Not more than 0.1%

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; Dasan Medichem Co., Ltd.; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Kim, Jae Hyung; Aum, Woon Yong; (12 pag.)KR2016/92976; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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 39603-24-2, Recommanded Product: 39603-24-2

General procedure: A mixture of substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

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:
Article; Dandia, Anshu; Khan, Shahnawaz; Soni, Pragya; Indora, Aayushi; Mahawar, Dinesh Kumar; Pandya, Prateek; Chauhan, Chetan Singh; Bioorganic and Medicinal Chemistry Letters; vol. 27; 13; (2017); p. 2873 – 2880;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, 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.

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem