Month: May 2021

Application of 341988-36-1, 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. 341988-36-1, name is Methyl indoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of methyl indoline-6-carboxylate (42) (50 mg, 0.28 mmol) in dichloromethane (10 mL) was cooled to -30 °C, treated with triethylamine (0.04 mL, 0.3 mmol) followed by dropwise addition of acetyl chloride (0.02 mL, 0.3 mmol), and warmed to RT. The reaction mixture was quenched with water and extracted with dichloromethane. The combined organic layers were washed with water, brine solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash-chromatography using ethyl acetate/hexane (3:7) to afford 49 mg 1-acetylindoline-6-carboxylate (43) as a white solid (80percent). 1H NMR (CDCl3, 400 MHz): 8.73 (s, 1H), 7.67 (d, 1H), 7.16 (d, 1H), 4.04 (t, 2H), 3.82 (s, 3H), 3.17 (t, 2H), 2.18 (s, 3H).); MS (electrospray): m/z = 220 [M+1].

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

Reference:
Article; Jeanguenat, Andre; Durieux, Patricia; Edmunds, Andrew J.F.; Hall, Roger G.; Hughes, Dave; Loiseleur, Olivier; Pabba, Jagadish; Stoller, Andre; Trah, Stephan; Wenger, Jean; Dutton, Anna; Crossthwaite, Andrew; Bioorganic and Medicinal Chemistry; vol. 24; 3; (2016); p. 403 – 427;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 6341-92-0, A common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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.

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, m.p. 196-198 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:
Patent; Pfizer Inc.; US4556672; (1985); A;; ; Patent; Pfizer Inc.; US4569942; (1986); A;; ; Patent; Pfizer Inc.; US4690943; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-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 5394-18-3, Computed Properties of C12H12BrNO2

General procedure: N-(4-mercaptobutyl) phthalimide (3) : N-(4-bromobutyl)-phthalimide (2, 2.81 g, 10 mmol) was dissolved in DMF (30mL) at room temperature. Sodium hydrosulfide (0.62 g, 11mmol) and TBAB (0.98 g) was added and stirred at room temperature under N2 atmosphere for 10 h. After the completionof the reaction (monitored by TLC analysis), the mixture was diluted with water and extracted with ethyl acetate (3×40 mL). The organic layer was washed twice with saturated brine (2×40 mL), dried over anhydrous sodium sulfateand the solvent was evaporated to dryness. The crude residue was purified by chromatography on silica (ethyl acetate/petroleum ether = 1/20) to afford pure 3 (2.00 g, 85% yield) as wax. 1H NMR (CDCl3, 400 MHz), delta: 1.44 (t, 1H, J=8.0Hz, S16H), 1.63-1.70 (m, 2H, C13H), 1.76-1.84 (m, 2H,C14H), 2.57 (q, 2H, C15H), 3.68 (t, 2H, J=6.9 Hz, C12H),7.72-7.82 (m, 4H, PhH); 13C NMR (CDCl3, 100 MHz), delta:24.0 (C15), 27.2 (C13), 31.0 (14), 37.1 (C12), 123.0 (C3,C6), 131.9 (C4, C5), 133.8 (C1, C2), 168.0 (C7, C9). (KunHu [17]: 1 H NMR (CDCl3, 500 MHz), delta: 1.26 (t, 1H, J = 7.0Hz), 1.63-1.69 (m, 2H), 1.77-1.83 (m, 2H), 2.55-2.59 (dd,2H, J = 7.0 Hz), 3.70 (t, 2H, J = 7.0 Hz), 7.72 (dd, 2H, J =3.0, 5.5 Hz), 7.84 (dd, 2H, J = 3.0, 5.5 Hz); 13C NMR(CDCl3, 125 MHz), delta: 24.09, 27.31, 31.10, 37.33, 123.24,132.11, 133.95, 168.39).

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, 2-(4-Bromobutyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shao, Yan-Dong; Song, Huang-Wang; Feng, Wen; Wang, Xiang-Hui; Shi, Zai-Feng; Wu, Lu-Yong; Chen, Guang-Ying; Lin, Qiang; Letters in Organic Chemistry; vol. 15; 3; (2018); p. 206 – 213;,
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. 3335-98-6, name is 1-Phenyloxindole, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar, was charged under an N2 atmosphere with the oxindole (2.25 mmol),Pd2(dba)3 (51 mg, 0.056 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (41 mg,0.112 mmol, 5 mol%), K2CO3 (932 mg, 6.75 mmol) and the aryl bromide(1.1 equiv), then sealed with a crimp-cap septum. Dioxane (5.0 mL, degassed) was added via syringe and the reaction was stirred in an oil bath at 100 C for 24 h. The reaction mixture was then cooled to room temperature and filtered through a Celite pad using EtOAc (15mL) as eluent. The filtered solution was washed with H2O (5 mL),dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column(30% EtOAc/hexanes) to afford the desired oxindole product.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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 7477-63-6 as follows. Product Details of 7477-63-6

General procedure: To a stirred mixture of isatins (1mmol) and malononitrile/ethyl cyanoacetate (1mmol) in methanol (3ml), was added piperidine (10molpercent) and the reaction mixture was stirred at room temperature for 10min. Then 5,7-dihydroxy-4-methyl-2H-chromen-2-one (1mmol) was added to it. The resulting mixture was stirred at reflux until the reaction was completed as indicated by TLC. The resulting precipitate was treated with dilute HCl and washed with water to afford the pure product for analysis.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pal, Suman; Khan, Md. Nasim; Karamthulla, Shaik; Choudhury, Lokman H.; Tetrahedron Letters; vol. 56; 2; (2015); p. 359 – 364;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 phthalimide (49 gm) was added to a solution of (Z)- 1 -phenyl- 1- diethylamino carbonyl-2-chloromethyl cyclopropane obtained in step-(c) at 20-30C. The reaction mixture was heated to 80-85C, stirred for 2-3 hrs at the same temperature and then cooled to 20-30C. The resulting reaction mixture containing (Z)- 1 -phenyl- 1- diethylaminocarbonyl-2-phthalimidomethyl cyclopropane was utilized in the next step without isolating the compound from the reaction mixture.

Statistics shows that Potassium 1,3-dioxoisoindolin-2-ide is playing an increasingly important role. we look forward to future research findings about 1074-82-4.

Reference:
Patent; MSN LABORATORIES LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; SATYANARAYANA, Revu; WO2012/46247; (2012); A2;,
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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6BrNO2

General procedure: 30 mg of SiO2_g-C3N4 nanocomposite was dispersed in aqueous media (3 ml) for 30 min and dimedone or 4-hydroxycoumarin (1 mmol), malononitrile (1 mmol) and isatin (1.0 mmol) were added to the mixture. Then, the mixture was stirred at reflux conditions for an appropriate time, while the reaction progress was monitored by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was employed for the extraction of crude product and the products were dried over anhydrous Na2SO4. The solvent was evaporated followed by recrystallizing of the crude product in hot ethanol, and pure products were identified by IR, 1H and 13C NMR spectral data. The SiO2_g-C3N4 nanocatalyst was washed with EtOH, dried and reused for the next run.

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; Allahresani, Ali; Taheri, Bahare; Nasseri, Mohammad Ali; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 1173 – 1188;,
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 100510-65-4 as follows. Safety of 6-Amino-3,3-dimethylindolin-2-one

570 mg (2.20 mmol) of ethyl 3-ethoxy-2-[(ethoxycarbonyl)carbamoyl]acrylate and 388 mg (2.20 mmol) of 6-amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one [for preparation see: US 2006/258689, page 35] were initially charged in 14 ml of ethanol and heated to reflux for 2 h. Subsequently, at RT, 247 mg (2.20 mmol) of potassium tert-butoxide were added and the mixture was stirred at RT for 1 h and at 60 C. for 1 h. For workup, the reaction mixture was admixed with water, acidified with 1N hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated. The residue was subjected to extractive stirring in MTBE/ ethyl acetate, and the solid formed was filtered off, washed with ethyl acetate and then dried at 50 C. under reduced pressure. This gave 630 mg (79% of theory) of the title compound. LC-MS (Method 1): Rt=0.65 min; MS (ESIpos): m/z=344 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.22 (t, 3H), 1.28 (s, 6H), 4.16 (q, 2H), 6.96-7.01 (m, 1H), 7.04-7.09 (m, 1H), 7.42 (d, 1H), 8.27 (s, 1H), 10.58 (s, 1H), 11.65 (s, 1H).

According to the analysis of related databases, 100510-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, category: indolines-derivatives

Step 1: 5-{[(2S)-2-(Phenoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a cold solution of 2,3-dioxo-2,3-dihydro-1-H-indole-5-sulfonylchloride (3.80 g, 15.5 mmol) in a 1:1 mixture of THF:CHCl3 (194 mL) was added drop-wise via syringe pump a solution of (2S)-2-(phenoxymethyl)pyrrolidine (2.85 g, 16.1 mmol, 1.03 eq) (J. Med. Chem, 44, 2014, 2001) and N,N-diisopropylethylamine (5.61 mL, 32.2 mmol, 2 eq) in CHCl3 (30 mL) over a period of 50 minutes under a dry N2 atmosphere with cooling in an ice bath. After stirring at room temperature for 64 hr the reaction mixture was concentrated and the crude product was flash chromatographed twice using Biotage KP silica gel, and gradient of 98/2 CH2Cl2/CH3OH as eluent on the first column and 90/10 CH2Cl2/CH3OH as eluent on the second column to give the title compound as a dark green solid (5.29 g, 88% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (ES-) m/z 385 [M-H]. MS: (ES+) m/z 387 [M+H].

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

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1498-88-0, name is 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline], 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. Quality Control of 1′,3′,3′-Trimethyl-6-nitrospiro[chromene-2,2′-indoline]

General procedure: Trifluoroacetic acid (13.9 mmol) was added to a solution of the corresponding hybrid compound 1a-c (13.9 mmol) in toluene (10 ml). For neutralization of acid the equimolar quantity of triethylamine was added. Spectrophotometric measurements for solutions were carried out on an Agilent Cary 60 Bio spectrophotometer in a KU-1 quartz cell with optical path length of 2 mm. The isomerization was investigated at room temperature for 0.2 mm solutions of 1a-c.

The synthetic route of 1498-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tuktarov, Airat R.; Khuzin, Artur A.; Dzhemilev, Usein M.; Mendeleev Communications; vol. 29; 2; (2019); p. 229 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem