Month: July 2021

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-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. Computed Properties of C9H9NO2

Description 13:5-Hydroxyindolin-2-oneTo 5-methoxyindolin-2-one (200 mg, 1.23 mmol) in dry DCM (5 ml), cooled down to 0C, was added a solution of boron tribromide in DCM (1M, 3.5 equiv., 4.3 ml). The reaction mixture was slowly warmed up to room temperature and stirred overnight, then carefully poured into stirring ice-water and stirred for 1 hour. The precipitate was collected by filtration, washed with water, air-dried to give the title compound as a grey solid. The results of NMR spectroscopy set out below indicate the final product was the title compound D13.’H NMR (dmso-d6): 10.06 (1 H, NH, br s), 8.93 (1H, OH. br s), 6.65 (1 H. s), 6.60-6.52 (2H, m), 3.37 (2H, s).13C NMR (dmso-d6): 176.1 , 152.2, 135.5, 126.9, 113.3, 112.3, 109.3, 33.1. MS: (MH+ 41) 191.0.

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
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Related Products of 1914-02-9, These common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, 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.

2d. 3,3-dimethyl-1-(2-nitrophenyl)indoline:; To 2c (317 mg, 2.12 mmol) was added 1-fluoro-2-nitrobenzene (200 mg, 1.42 mmol). The reaction mixture was stirred at 175 C. for 8 h. The reaction mixture was diluted with CH2Cl2 and washed with 1N HCl and dried over Na2SO4. The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 10% EtOAc in hexane over 30 min as eluting solvent to afford 2d (360 mg, 95%) as an oil. MS (ES) m/z 269 [M+H]+

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2006/293281; (2006); A1;,
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Synthetic Route of 1336963-95-1, 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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example Dl, Step 3. To a solution of the 6-bromoindoline-2,3-dione (e.g., 6-bromo-7- fluoroindoline-2,3-dione, 1 equiv) in 1 Nu NaOH (0.14 M) was added H202 (1.8 M) dropwise and the resulting mixture was stirred at room temperature until the reaction was complete (approximately 2 hours). The mixture was filtered and the filtrate was acidified to pH 2 with hydrochloric acid. The precipitate that formed was filtered, washed with water, and concentrated to provide the 2-amino-4-bromobenzoic acid (e.g., 2-amino-4-bromo-3-fluorobenzoic acid).

The synthetic route of 6-Bromo-7-fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEFFERNAN, Michele, L., R.; HARDY, Larry, Wendell; WU, Frank, Xinhe; SARASWAT, Lakshmi, D.; SPEAR, Kerry, L.; WO2012/170845; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 5394-18-3,Some common heterocyclic compound, 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, molecular formula is C12H12BrNO2, 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.

N-(4-Bromobutyl)phthalimide (1.5 g, 5.32 mmol) was suspendedin THF (48 mL) and treated with sodium iodide (0.80 g, 5.32 mmol), triethylamine (0.74 mL, 5.32 mmol) and morpholine (0.51 mL, 5.85 mmol). The mixture was then heated at reflux for 16 h. After cooling to ambient temperature, the solvent was removed in vacuo and the residue partitioned between H2O (100 mL) and CHCl3 (100 mL). The aqueous layer was further extracted with CHCl3 (100 mL) and the organic extracts combined, dried (MgSO4), filtered, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chromatography on silica eluting with ethyl acetate to give phthalimide10 (1.02 g, 66%) as a pale yellow oil; numax/cm-12942, 2855, 2807, 1703, 1393, 1359, 1333, 1114, 1069, 1011, 862, 716, 528; deltaH (300 MHz; CDCl3) 7.86-7.77 (2 H, m), 7.73-7.67 (2 H, m), 3.69 (6 H, m), 2.40 (6 H, m), 1.71 (2 H, m), 1.50 (2 H, m); deltaC (75 MHz; CDCl3) 168.5, 134.0, 132.2, 123.3, 66.9, 58.4, 53.7, 37.9, 26.6, 23.8; m/z (+ESI) 289 ([M + H]+, 100); Found: M+, 289.15493. C16H20N2O3 requires 289.15467.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromobutyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Article; Beinat, Corinne; Reekie, Tristan; Hibbs, David; Xie, Teresa; Olson, Thao T.; Xiao, Yingxian; Harvey, Andrew; O’Connor, Susan; Coles, Carolyn; Tsanaktsidis, John; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 200 – 205;,
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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. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8BrN

A solution of 5-bromo-2,3-dihydro-1H-indole (4.97 g, 25.1 mmol), di-tert-butyl dicarbonate (6.0 g, 27.5 mmol) and 4-dimethylaminopyridine (catalytic) in dichloromethane (70 mL) was stirred at room temperature until the starting material was consumed. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel, eluted with ethyl acetate/hexane to give the product, 4.1 g (55%). 1H NMR (CDCI3) : delta 1.55 (s, 9 H), 3.06 (t, 2 H), 3.97 (t, 2 H), 7.23-7.27 (m, 2 H) and 7.72 (br m, 1 H).

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 22190-33-6.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/69792; (2004); A2;,
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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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 20870-79-5

Preparation of 5-amino-oxindole (2) To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 hours. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%).

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 20870-79-5.

Reference:
Patent; Pfizer Inc; US2005/256145; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7147-90-2, 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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

3.6 g of 1,1, 1-trifluoro-3-iodopropane are added dropwise to a mixture of 7.5 g of 4- chlorophthalimide and 4.6 g of potassium carbonate in 40 cm3 of [DIMETHYLFORMAMIDE] at a temperature in the region of [110C] with stirring. After stirring for 11 hours at a temperature in the region of [120C,] the reaction mixture is cooled to a temperature in the region [OF 20C] and then poured into 200 cm3 of water. The mixture is acidified with dilute aqueous hydrochloric acid solution to a pH of about 3, and is then extracted 3 times with 100 cm3 of ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness. 5.0 g [OF 4-CHLORO-N- (3,] 3, 3-trifluoro- propyl) phthalamic acid are thus obtained, Rf = 0.12 (thin layer chromatography on silica gel, eluent : ethyl acetate)

The chemical industry reduces the impact on the environment during synthesis 5-Chloroisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AVENTIS PHARMA DEUTSCHLAND GMBH; WO2003/101450; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

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; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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Related Products of 7147-90-2, The chemical industry reduces the impact on the environment during synthesis 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

To a solution of 5-chloro-isoindole-l,3-dione (5.0 g, 27.5 mmol) in DCM (200 mL) was added ethylmagnesium chloride (2 M in THF, 41.3 mL) dropwise at 0 C. After the addition, the mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regioisomers (5.82 g, 100%). MS: 212.0 (M+H+).; Under N2 protection, triethylsilane (19.3 g, 166 mmol) and TFA (20 mL) were added successively to a mixture of 5-chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol- 1 -one and 6- chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol-l-one (3.52 g, 16.6 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. solution of NaHCC>3 (30 mL) and extracted with DCM (2 x 30 mL). The combined organic layers were washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude mixture of products. Both 5-chloro-3-ethyl-2,3-dihydro-isoindol-l-one (0.65 g, 20%) MS: 196.1 – 147 -(M+H+) and 6-chloro-3-ethyl-2,3-dihydro-isoindol-l-one (0.62 g, 19%) MS: 196.1 (M+H+) were obtained by prep-HPLC separation as white solids.

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, 5-Chloroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3485-84-5, name is N-Vinylphthalimide, 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 3485-84-5, Safety of N-Vinylphthalimide

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (64 mg, 0.29 mmol), acetonitrile (50 mL), JV-vinylphthalimide (1.19 g, 6.89 mmol), triethylamine (2.4 mL, 17 mmol), tri-o-tolylphosphine (260 mg, 0.86 mmol) and l-(7-bromo-2-ethyl-17f-imidazo[4,5-c]quinolin-l-yl)-2-methylpropan-2-ol (2.00 g, 5.74 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120 0C in an oil bath for 16 hours. The reaction was cooled to ambient temperature and silica gel (20 g) was added followed by concentration under reduced pressure. The sample absorbed on silica was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-7% gradient of methanol in dichloromethane). The recovered solid was washed with 1% aqueous sodium carbonate to provide 1.95 g of 2-{2- EPO [2-ethyl- 1 -(2-hydroxy-2-methylpropyl)- 1 H-imidazo[4,5 -c]quinolin-7-yl]ethenyl} – 1 H- isoindole-l,3(2H)-dione as a bright yellow solid. MS (APCI) m/z 441 (M + H)+.

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

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