Month: March 2021

Synthetic Route of 24566-79-8, A common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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: A mixture of the corresponding secondary amine 3a-d [23] (5.5mmol), anhydrous K2CO3 (6mmol) and compounds 2a-d (5mmol) were added in CH3CN (20ml). The mixture was heated at 65C for 8-10h. The solvent was evaporated under reduced pressure. Then water (25mL) was added, and the mixture was extracted with dichloromethane (20mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated under vacuum. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to obtain the oil products 4-7.

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; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Xu, Rui; Cao, Zhongcheng; Song, Qing; Wang, Ting; Zhang, Xiaoyu; Liu, Hongyan; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 307 – 323;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: A oven dried flask containing an appropriate dicarbonyl compound 15 (isatin or acenaphthoquinone or ninhydrin, 0.5 mmol), an appropriate alpha-amino acid 16 (sarcosine or l-proline, 0.6 mmol) and an appropriate dipolarophile 6 (0.5 or 1 mmol) in an appropriate dry solvent (3-4 mL) was heated to the temperature and time as shown in the respective Tables/Schemes. Then, the reaction mixture was cooled to rt and the solvent was evaporated in vacuo, which afforded a crude reaction mixture. Then, the crude mixture was subjected to the silica gel column chromatography purification (EtOAc/hexane), which gave the corresponding spiro-pyrrolidine/pyrrolizidines containing heteroaryl moieties 17/18/19 (see the corresponding Tables/Schemes for specific entries).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Rajkumar, Vadla; Babu, Srinivasarao Arulananda; Padmavathi, Rayavarapu; Tetrahedron; vol. 72; 36; (2016); p. 5578 – 5594;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Bromomethylphtalimide (85 mg, 0.35 mmol), sodium iodide (53 mg, 0.56 mmol) and cesium carbonate (177 mg, 0.54 mmol) were added to a solution of DO3AtBu under argon atmosphere (172 mg, 0.33 mmol) in freshly distilled acetonitrile (5 mL). The suspension was heated to reflux for 24 h, before being filtered at room temperature. The yellow filtrate was evaporated under reduced pressure and 10 mL chloroform was added in order to precipitate residual inorganic impurities. Evaporation of the solvent and addition of 20 mL of ether led to precipitation of a yellow powder corresponding to the sodium adduct C35H55N5O8.NaI.H2O (191 mg, 67% yield). 1H NMR (CDCl3) d: 7.82-7.71 (m, 4H), 4.66 (s, 2H), 3.27-2,34 (broad signals overlapping, 22H), 1.48-1,40 (two signals overlapping, 27H); 13C NMR (CDCl3) d: 173.91, 173.30, 169.70, 134.58, 131.69, 123.59, 83.03, 82.73, 57.62, 56.48, 55.69, 53.55, 51.77, 51.15, 48.34, 28.06, 27.88. Anal. Calcd for C35H55N5O8.NaI.H2O: C, 49.94; H, 6.83; N, 8.32. Found: C, 50.13; H, 6.67; N, 8.49.

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

Reference:
Article; De La Reberdiere, Arnaud; Lachaud, Fabien; Chuburu, Francoise; Cadiou, Cyril; Lemercier, Gilles; Tetrahedron Letters; vol. 53; 45; (2012); p. 6115 – 6118,4;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

The synthetic route of 2-(Bromomethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3485-84-5, name is N-Vinylphthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: N-Vinylphthalimide

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (17 mg, 0.08 mmol), acetonitrile (50 mL), vV-vinylphthalimide (716 mg, 4.13 EPO mmol), triethylamine (1.6 niL, 11 mmol), tri-o-tolylphosphine (69 mg, 0.22 nimol) and 1- {3-[8-bromo-2-(2-methoxyethyl)-lH’-imidazo[4,5-c]quinolin-l-yl]propyl}pyrrolidin-2-one (1.62 g, 3.76 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 1200C in an oil bath for 15 hours. The reaction was cooled to ambient temperature and methanol (50 niL) and chloroform (50 ml) were added. After filtering through a 0.2 micron PTFE membrane, the solution was concentrated under reduced pressure and then purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-8% gradient of methanol in dichloromethane) to provide 2.0 g of2-(2-{2-(2-methoxyethyl)-l-[3-(2-oxopyrrolidin-l-yl)propyl]-lH-imidazo[4,5- c]quinolin-8-yl}ethenyl)-lH-isoindole-l,3(2H)-dione as a bright yellow solid. MS (APCI) m/z 524 (M + H)+.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2006/91394; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0, These common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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: Indole (0.234 g, 2 mmol) and isatin (0.147 g, 1 mmol) were mixed in oxalic acid: proline (5 ml) as solvent and the resultant mixture was stirred at room temperature for appropriate time. After the completion of the reaction indicated by TLC, 5 ml distilled water was added. The insoluble crude product was filtered, washed with distilled water and recrystallized from ethanol.

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chandam, Dattatray; Mulik, Abhijeet; Patil, Prasad; Jagdale, Suryabala; Patil, Dayanand; Sankpal, Sandeep; Deshmukh, Madhukar; Journal of Molecular Liquids; vol. 207; (2015); p. 14 – 20;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 2-oxoindoline-6-carboxylic acid (1.2 g, 6.77 mmol, 1.00 equiv), sulfuric acid (98%, catalytic amount) in CD3OD (50 mL) was stirred for 24 hours at 60 C. The reaction mixture was cooled to room temperature and the filtrate was concentrated under vacuum and poured into ice water. The pH was adjusted to 8 with NaHCO3 and the aqueous solution was extracted with ethyl acetate. The ethyl acetate was concentrated and the residue applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:5) to give the title product 1.0 g (75%) as a brown solid. 1H NMR (400 MHz, CDCl3) delta: 10.54 (s, 1H), 10.50 (s, 1H), 7.58 (m, 1H), 7.34 (d, J=7.8 Hz, 2H), 3.45 (s, 2H).

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-Oxoindoline-6-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (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. 15861-23-1, name is Indoline-5-carbonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H8N2

To a solution of 5-cyanoindoline (0.5 g, 3.47 mmol) and the compound of Part D (1.3 g, 1.1 eq.) in 10 mL of DMF was added sodium hydride (60% in oil, 0.15 g, 1.1 eq.). The mixture was stirred overnight at rt. The reaction was diluted with water and extracted 3¡Á with EtOAc. The combined extracts were washed with water and brine and then dried over Na2SO4, filtered and evaporated. Flash chromatography on silica gel (hexane/CH2Cl2/EtOH 20/80/0.5) provided the desired alkylated product (0.44 g, 31%, MS m/z 414.2 (M+H)+) along with 68% of unreacted starting material.

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; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); 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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., SDS of cas: 3485-84-5

4-Fluorophenyl benzaldehyde-tosylhydrazone sodium salt (1.57 g, 5 mmol), N-vinyl-phthalimide (2.59 g, 15 mmol), benzyltriethylammonium chloride (114 mg, 0.5 mmol), and rhodium acetate dimer (22 mg, 0,05 mmol) were stirred with dioxane (23 ml) to give a thick slurry. This was stirred overnight at room temperature. TIc (20% EtOAc/hexane) showed good conversion, so the mixture was shaken between EtOAc and water. The organic phase was dried with MgSO4 and evaporated to yield 3.8 g of a crude mixture. This was chromatographed on silica with EtOAc/hexane to yield 169 mg (12%) of 2-[cis-2-(4-fluoro-phenyl)cyclopropyl]-isoindole-1,3-dione 1H-NMR (CDCl3) 1.60 (1H, ddd, 7.7, 7.7, 7.7 Hz); 2.19 (1H, ddd, J=7.7, 7.3, 4.9 Hz); 2.51 (ddd, J=7.3, 7.3, 7.3 Hz); 3.08 (1H, ddd, 7.7, 7.7, 4.9 Hz); 6,81 (2H, dd, J=8.8, 8.8 Hz); 7.06 (2H, dd, J=8.8, 5.1); 7.55 (2H, m); 7.61 (2H m).

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; SYNGENTA PARTICIPATIONS AG; O’Sullivan, Anthony Cornelius; Loiseleur, Olivier; Stierli, Daniel; Luksch, Torsten; Pitterna, Thomas; US2014/378461; (2014); 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 496-12-8 as follows. HPLC of Formula: C8H9N

EXAMPLE 1 Preparation of (1,3-Dihydro-isoindol-2-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone; A mixture of 0.387 mmol 2-isopropoxy-5-methanesulfonyl-benzoic acid (example B1), 0.464 mmol 2,3-Dihydro-1H-isoindole (commercial), 0.426 mmol TBTU and 1.935 mmol DIPEA in 1.4 ml DMF was stirred at RT for 2 h. The reaction mixture was evaporated in vacuo. The residue was taken in water and extracted with ethylacetate. The combined organic phases were washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light brown solid (88% yield). MS (m/e): 360.2 [M+H]+, 100%)

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jolidon, Synese; Narquizian, Robert; Norcross, Roger David; Pinard, Emmanuel; US2006/178381; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem