Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 60434-13-1, name is 5-Chloro-1-methylindoline-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 60434-13-1, Computed Properties of C9H6ClNO2

General procedure: A solution of N-methylisatin (161 mg, 1.0 mmol), N-methylindole (262 mg, 2.0 mmol), and p-TsOH . H 2 O (19 mg, 0.1 mmol) in CH 2 Cl 2 (2.0 mL) was stirred at room temperature for 1 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 2:1), 1a was obtained as a white solid, 301 mg (74%). 1 Other compounds 1b-f, 1i, 1j, and 1n were synthesized similarly, and compounds 1a1 and 1n1 are known compounds. The spectroscopic data of unknown compounds 1b-f, 1i, and 1j are as follows.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Seo, Da Young; Kim, Gieun; Jo, Hwi Yul; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 39; 4; (2018); p. 587 – 590;,
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. 39755-95-8, name is 5-Methoxyisatin, A new synthetic method of this compound is introduced below., Quality Control of 5-Methoxyisatin

A mixture of 5-methoxyisatin (2.84 g, 16 mmol) and K2CO3 (5.53 g, 40mmol) was dissolved in anhydrous DMF (12 mL) under Ar. Benzylbromide (5.71 mL, 48 mmol) was added dropwise and the mixturewas stirred at r.t. for 19 h. The mixture was extracted with dichloromethane (3 × 20 mL) and the organic phase was washed with H2O (20mL) and brine (20 mL), dried with MgSO4, filtered, and concentratedto obtain a red solid.14The crude material was dissolved in DMSO (12mL), hydrazine hydrate (1.81 mL, 32 mmol) was added dropwise andthe mixture was heated at 150 C for 5 h. The mixture was cooled tor.t., extracted with EtOAc (2 × 100 mL), and the organic phase waswashed with H2O (100 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (hexane/EtOAc) to give pure 1-benzyl-5-methoxy-2-oxindole (2.55 g, 63%) as a brown oil.15The above product was dissolved in acetic anhydride (11.5 mL, 121mmol) and DMAP (37 mg, 0.3 mmol) was added. The mixture was heated at reflux (140 C) for 6 h and then cooled to r.t. and evaporated under reduced pressure. The residue was dissolved in MeOH (40 mL)cooled at 0 C and then a solution of KOH (8.5 g, 151 mmol) in MeOH (60 mL) was added. The solution was stirred at r.t. for 18 h then the solution was cooled in an ice-bath at 0 C and 12 M aqueous HCl was added until pH 3. The organic solvent was evaporated under reduced pressure, H2O (50 mL) was added and the mixture was extracted with EtOAc (3 × 50 mL). The organic phase was dried over MgSO4, filtered,and concentrated. The residue was purified by flash chromatography(hexane/EtOAc) to give pure 2c.

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; Ortega-Martinez, Aitor; Molina, Cynthia; Moreno-Cabrerizo, Cristina; Sansano, Jose M.; Najera, Carmen; Synthesis; vol. 49; 23; (2017); p. 5203 – 5210;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3891-07-4, These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, 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.

PREPARATION 7 Preparation of ethyl 4-[2-(phthalimido)ethoxy]acetoacetate STR52 Sodium hydride (57% [by weight] in oil, 66.1 g) was stirred in dry tetrahydrofuran (500 ml) under nitrogen at -10 while N-(2-hydroxyethyl)phthalimide (150 g) was added. To this slurry was added at -10 a solution of ethyl 4-chloroacetoacetate (129.3 g), in dry tetrahydrofuran, over 1 hour. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 18 hours. This mixture was poured into 1N hydrochloric acid (800 ml) and ethyl acetate was added (750 ml). The aqueous layer was washed with ethyl acetate (300 ml) and the organic solutions were combined. After washing with water (300 ml), the ethyl acetate was evaporated to give the title compound as a crude oil (243 g), sufficiently pure for further use.

Statistics shows that 2-(2-Hydroxyethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 3891-07-4.

Reference:
Patent; Pfizer Inc.; US4572909; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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: Phthalimidine (800 mg, 6.01 mmol) was dissolved in THF(40 mL). At ambient temperature triethylamine (670 mg,6.62 mmol) was added dropwise and the mixture was stirred for5 min, whereupon dichlorophenylphosphine (538 mg, 3.01 mmol)was added and the mixture was stirred for one day. Thereafter thewhite precipitate was filtered and washed with THF (3 mL). Thecombined filtrate and washings were evaporated to dryness (condensationof volatiles into a cold trap under reduced pressure), theresidue was dissolved in THF (10 mL) and the solution was filteredthrough Celite. After vapor diffusion of n-pentane into the filtrate(for one week), white crystalline product suitable for single-crystalX-ray diffraction was obtained. The supernatant was removed bydecantation, the white solid was washed with n-pentane (3 mL)and dried in vacuo to yield 480 mg (1.29 mmol, 43%) of 1b.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gericke, Robert; Wagler, Joerg; Polyhedron; vol. 125; (2017); p. 57 – 67;,
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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Isoindoline

General procedure: Naphthylboronic acid (0.25 g, 1.5 mmol) was added with 0.094 g of phenol (1.0 mmol) to 15 mL of DCM. Copper(II) acetate (0.36 g, 2.0 mmol) was then added along with triethylamine (0.5g, 5.0 mmol), and the dismembrator horn placed in the reaction vessel. The sonicator was set to 55 watts and the reaction was allowed to proceed for 4 hours (1 minute pulse with a 3 second rest). Post reaction, the product was isolated by column chromatography. Product yields were determined by weight and purity was confirmed by GC/MS and NMR.

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 496-12-8.

Reference:
Article; Musolino, Bryan J.; Kabalka, George W.; Heterocycles; vol. 90; 1; (2015); p. 271 – 297;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 317-20-4, These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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.

Potassium hydroxide (1.58 g; 28.16 mmol; 3.10 eq.) was added portion wise to a solution of 7-Fluoro-1H-indole-2,3-dione (1.50 g; 9.08 mmol; 1.00 eq.) in acetone (1.00 ml; 13.63 mmol; 1.50 eq.), ethanol (4.50 ml) and water (1.50 ml) in a microwave tube. The reaction was placed in a microwave oven and heated at 100 C. for 20 min. The reaction mixture was concentrated under vacuum. Water was added followed by a 5N solution of hydrochloric acid until the pH of the solution reached 4. The suspension was then filtered and the solid obtained dried. 8-fluoro-2-methylquinoline-4-carboxylic acid (1.60 g; 85.84%) was isolated as a brown solid

Statistics shows that 7-Fluoroisatin is playing an increasingly important role. we look forward to future research findings about 317-20-4.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; OUVRY, Gilles; HARRIS, Craig Steven; BHURRUTH-ALCOR, Yushma; (65 pag.)US2017/247353; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 11 (FROM TABLE 3) 3-[5-(6-Chloro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-4-methyl-1H-pyrrol-3-yl]-propionic acid 4-(2-Carboxyethyl)-2-formyl-3-methylpyrrole (200 mg), 167.6 mg 6-chloro-2-oxindole, and 166 muL piperidine in 2 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven to give 246 mg (74%) of the title compound as a brown solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.22 (s, br, 1H, NH-1′), 12.09 (s, br, 1H, COOH), 10.95 (s, br, 1H, NH-1), 7.78 (d, J=7.95 Hz, 1H, H-4), 7.66 (s, 1H, H-vinyl), 7.18 (d, J=2.64 Hz, 1H, H-2′), 7.01 (dd, J=1.90, 7.95 Hz, 1H, H-5), 6.86 (d, J=1.90 Hz, 1H, H-7), 2.65 (t, J=7.14 Hz, 2H, CH2CH2COOH), 2.45 (t, J=7.14 Hz, 2H, CH2CH2COOH), 2.26 (s, 3H, CH3).

The chemical industry reduces the impact on the environment during synthesis 6-Chlorooxindole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

65826-95-1, name is 5-Methylindoline, 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. Application In Synthesis of 5-Methylindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 percent ethyl acetate in petroleum ether to afford compound (4).

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

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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 61 5-(6-(6-nitroindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo-[2,3-b]pyridin]-2′(1’H)-one 150 mg (0.37 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid-hydrochloride, 60 mg (0.37 mmol) 4-nitroindole, 0.15 mL (0.87 mmol) DIPEA and 130 mg (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. Then the reaction mixture was diluted with water/MeOH, the precipitate formed was suction filtered and washed with plenty of water. The precipitate was dried. Yield: 165 mg (74% of theory) ESI-MS: m/z=520 (M+H)+ Rt (HPLC-MS): 1.56 min (method C)

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem