Month: March 2021

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. 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H6BrNO

7-Bromo-2,3-dihydro-1H-isoindol-1-one (10 g, 47.16 mmol) was added to concentrated H2SO4 (80 mL) at 0 C. and the resulting solution stirred at 0 C. for 0.5 h. N-Iodosuccinimide (15.92 g, 70.74 mmol) was then added and the reaction mixture stirred at 0 C. for 2 h. The reaction mixture was poured on to ice and a precipitate collected by filtration. The solid collected was washed with sat. aq. sodium sulfite (200 ml), water (200 ml) and dried under vacuum to afford crude product as a brown solid. The crude product was triturated with MeOH and the solid obtained dried under vacuum to afford 7-bromo-6-iodo-2,3-dihydro-1H-isoindol-1-one (4.3 g, 27%) as white solid; 1H NMR (400 MHz, DMSO, 30 C.) 4.27 (2H, s), 7.37 (1H, d), 8.11 (1H, d), 8.74 (1H, s); m/z: ES+ [M+H]+=340.

The synthetic route of 200049-46-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
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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 6326-79-0 as follows. Formula: C8H4BrNO2

To R4 (500 mg, 2.21 mmol) in acetonitrile (15 mL) is added Mel (0.303 mL, 4.87 mmol) and K2CO3 (1.2 g, 8.68 mmol) and the reaction mixture stirred at 60 C for 45 min DCM and water is added and the aqueous layer extracted twice with DCM, the combined organic layers are washed with brine, dried and concentrated. Yield 65%. m/z 240/242 [M+H]+, rt 0.49 min, LC-MS Method b.

According to the analysis of related databases, 6326-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; WO2013/41497; (2013); A1;,
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Related Products of 60434-13-1,Some common heterocyclic compound, 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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-OBoc-oxindoles 3a and 3e-g were synthesized by following our earlier reportedproceudure.1 In a 100ml round bottom flask was charged with 1g of N-protected isatin, 1equivalent of CeCl3.7H2O and the mixture was dissolved by methanol (2mL/mmol) then0.5equivalent of NaBH4 was added portion wise at 0 C. After addition of NaBH4 the reactionmixture was quenched imidiately by excess of ice and taken extract with ethylacetate twice. Theorganic fractions was combined and dried over anhydrous Na2SO4 and evaporated through rotary vacuum.

The synthetic route of 60434-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jayakumar, Samydurai; Kumarswamyreddy, Nandarapu; Prakash, Muthuraj; Kesavan, Venkitasamy; Organic Letters; vol. 17; 5; (2015); p. 1066 – 1069;,
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Application of 56341-37-8, A common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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: Appropriate indolin-2-one or indoline-2-thione (0.3 g) was mixed with acetic anhydride (3 mL) and 4-dimethylaminopyridine (DMAP, 1 mol %). The mixture was heated at 150 C in a round-bottomed flask equipped with an air condenser and CaCl2 guard tube. The reaction time for each reactant is provided in [Table 2] and [Table 3]. After the completion of the reaction excess acetic anhydride was evaporated under reduced pressure. The solid residue obtained in the case of the triacetylated products was suspended in cold methanol and vacuum filtered. The product collected was thoroughly washed with hexane and dried. In the case of mono and diacetylated products the solid residue was purified using flash column chromatography (FCC) (silica gel, hexanes/ethyl acetate).

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jha, Mukund; Chou, Ting-Yi; Blunt, Brian; Tetrahedron; vol. 67; 5; (2011); p. 982 – 989;,
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Indoline | C8H9N – PubChem

Application of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: GN/SO3H (80 mg) was added to the 3 mL of EtOH/water (1:1) and dispersed for 30 min. Then, malononitrile (1 mmol), isatin (1 mmol), and dimedone (1 mmol) were added to the mixture and the mixture was heated to reflux and kept at this temperature for an appropriate time. After the time of reaction was completed, water was separated by centrifuging followed by extracting the crude product by ethyl acetate. The solvent was dried using Na2SO4 and removed from the reaction by evaporation with a rotary evaporator. Finally, the crude product was recrystallized in hot ethanol to achieve the pure product. The GN/SO3H nanocomposite was washed and reused several times.

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; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6979 – 6993;,
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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. 366452-98-4, name is 4-Amino-2,3-dihydro-1H-isoindol-1-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Amino-2,3-dihydro-1H-isoindol-1-one

400 mg (1.297 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl)-pentanal is stirred with 192.1 mg (1.297 mmol) of 4-amino-2,3-dihydroisoindol-1-one in 1.89 ml of glacial acetic acid for four days at room temperature. The mixture is mixed three times with toluene and evaporated to the dry state in a rotary evaporator. The residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 429.7 mg (75.5%) of the desired compound is isolated. 1H-NMR (300 MHz, CDCl3): delta=1.37 (3H), 1.52 (3H), 2.22 (1H), 3.42 (1H), 3.84 (3H), 4.37 (2H), 4.68 (1H), 6.53-6.68 (3H), 6.72-6.95 (2H), 7.37 (1H), 7.49 (1H), 7.75 (1H).

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 366452-98-4.

Reference:
Patent; Rehwinkel, Hartmut; Baeurle, Stefan; Berger, Markus; Schmees, Norbert; Schaecke, Heike; Krolikiewicz, Konrad; Mengel, Anne; Nguyen, Duy; Jaroch, Stefan; Skuballa, Werner; US2005/131226; (2005); A1;,
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. name: 5-Acetylindolin-2-one

EXAMPLE 43 A solution of 5-acetyloxindole (272 mg, 1.56 mmol), (EP 0155828 A2), in DMF (1.5 ml) was added dropwise to a suspension of sodium hydride (62 mg, 1.56 mmol, prewashed with hexane) in DMF (3 ml) and, the mixture stirred for 30 minutes at ambient temperature. 4-Chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (175 mg, 0.52 mmol), (prepared as described for the starting material in Example 5), was added and the mixture was heated at 50 C. for 1.5 hours. The mixture was poured into a mixture of ether (30 ml), ethyl acetate (30 ml) and water (50 ml). The aqueous layer was separated and adjusted to pH7.8 with 2M hydrochloric acid and extracted with methylene chloride. The organic extracts were washed with water, brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluding with methylene chloride/methanol (90/10). The purified solid was dissolved in methylene chloride/methanol and 7M ethanolic hydrogen chloride (1.5 ml) was added. The volatiles were removed by evaporation, the residue collected and dried under vacuum to give 4-(5-acetyloxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline hydrochloride (135 mg, 48%). 1H NMR Spectrum: (DMSOd6, CD3CO2D) 2.33(m, 2H); 2.54(s, 3H); 3.15(t, 2H); 3.37(t, 2H); 3.54(d, 2H); 3.73(t, 2H); 3.85(s, 3H); 4.03(d, 2H); 4.33(t, 2H); 7.09(d, 1H); 7.35(s, 1H); 7.8(s, 1H); 7.87(d, 1H); 8.25(s, 1H); 8.8(s, 1H). MS-ESI: 477 [MH]+

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:
Patent; Zeneca Limited; US6265411; (2001); B1;,
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Indoline | C8H9N – PubChem

Application of 337536-15-9,Some common heterocyclic compound, 337536-15-9, name is 4-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

A 0 C solution of Example 1C (5g, 23.6 mmol) in 10 mL sulfuric acid was treatedwith a solution of concentrated nitric acid (1.55 mL, 24.7 mmol) in 10 mL sulfuric acid viaaddition funnel. The resulting mixture was stirred at 0 C for 1 hour, warmed to roomtemperature, stirred overnight, poured over ice, and filtered. The filter cake was washed withwater and diethyl ether and then dried to give 5.39g of the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/108672; (2004); A1;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3783-77-5, name is 2-(3-Oxobutyl)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 3783-77-5, Product Details of 3783-77-5

5.43 g (25 mmol) of 4-phthalimidobutan-2-one Z4 are dissolved in 150 ml of toluene, admixed with 4.28 g (56.25 mmol, 2.25 eq) of 1,3-propanediol and 0.24 g (1.25 mmol, 0.05 eq) of para-toluenesulfonic acid monohydrate and heated under reflux for 24 h on a water separator. The mixture is cooled to RT and washed with 3¡Á30 ml of saturated sodium hydrogencarbonate solution. The combined aqueous phases are extracted once with 90 ml of EtOAc and the combined organic phases are dried over sodium sulfate and concentrated on a rotary evaporator. The colorless oil obtained is crystallized from heptane. Yield (Z6): 7.09 g with an HPLC purity of 88 area % 1H-NMR (CDCl3): 7.89-7.80 (m, 2H); 7.74-7.66 (m, 2H); 3.97-3.80 (m, 6H); 2.11 (tr, 2H); 1.84-1.72 (m, 1H); 1.66-1.56 (m, 1H); 1.48 (s, 3H) [ppm]

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:
Patent; BASF SE; SUBKOWSKI, THOMAS; Bollschweiler, Claus; Wittenberg, Jens; Siegel, Wolfgang; Pelzer, Ralf; (92 pag.)US2017/265510; (2017); A1;,
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Indoline | C8H9N – PubChem

Related Products of 181140-34-1, 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of (R)-(-)-N-(2,3-epoxypropyl)phthalimide 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals.

The synthetic route of (R)-(-)-N-(2,3-Epoxypropyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir; Tetrahedron Asymmetry; vol. 22; 5; (2011); p. 541 – 549;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem