Month: February 2021

Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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. HPLC of Formula: C11H11NO3

Resin 2.7; – To all of the resin 2.6 obtained above suspended in 30 mL of dry THF is added as solids 11.02 g (42 mmole, 3 equiv) of triphenylphosphine and 8.62 g (42 mmole, 3 equiv) of N-(3-hydroxypropyl)phthalimide. The resulting suspension is agitated with a slow stream of argon through the bottom of the vessel while 8.49 g (42 mmole, 3 equiv) of diisopropylazodicarboxyate is introduced in a dropwise fashion. The resulting suspension is agitated for 18 h at 25C when the solvents are filtered and washed with CH2C12, ‘PrOH, DMF, THF then CH2C12 (3 x 75 mL each). The resin is dried under vacuum overnight to give a product that is negative by the Kaiser amine test reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 883-44-3, its application will become more common.

Reference:
Patent; MEDIQUEST THERAPEUTICS, INC.; WO2005/105729; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Activation of 2-(2-hydroxyethyl)isoindoline-1,3-dione to Form VA To the mixture of commercially available 2-(2-hydroxyethyl) isoindoline-1,3-dione (8.8 g. 1.00 equiv) and triethylamine (5.8 g, 1.25 equiv) in methylene chloride (69 mL) is added benzenesulfonyl chloride (9.3 g, 1.05 equiv) dropwise at under about 25 C. The mixture is stirred at room temperature until the reaction is complete as determined by HPLC. The reaction mixture is washed with an aqueous solution of sodium bicarbonate. The organic solution is concentrated under reduced pressure and the product is precipitated by adding hexanes (83 mL) to the residue. VA is isolated by filtration (15.1 g, 99% yield). 1H NMR (400 MHz, DMSO-d6): delta 7.77-7.82 (m, 4H), 7.71 (d, J=8.0, 2H), 7.52 (t, J=8.0, 1H), 7.41 (t, J=8.0, 2H), 4.29 (t, J=4.0, 2H), 3.81 (t, J=4.0, 2H).

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

Reference:
Patent; Gilead Sciences, Inc.; Chiu, Anna; Feng, Yanshu; Gao, Hanrong; Kerschen, James A.; Reichwein, John; Sarma, Keshab; Thompson, Andrew S.; Zhao, Xinjun; US2015/225384; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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 38 Preparation of Ethyl 2-(1-oxo-6-vinylphthalazin-2(1H)-yl)acetate (BI24) Step 1. 5-Bromo-3-hydroxyisoindoline-1-one (BI25) A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g, 0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-1,3-dione (5 g, 22 mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C. for 30 min and 3 h at ambient temperature. The reaction mixture was filtered and the filtrate was neutralized with concentrated HCl. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261 C.; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J=9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]-); IR (thin film) 1684, 3246, 606 cm-1.

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

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
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 20870-79-5 as follows. name: 5-Nitroindolin-2-one

A. A suspension of 5-nitroindolin-2-one (2.0 g, 11.13 mmol), and 10% palladium on carbon (500 mg) in methanol (100 mL) was hydrogenated for 2 hours under 45 psi. The reaction mixture was filtered through celite and the resulting cake was washed with methanol. The filtrate was concentrated to afford 5-aminoindolin-2-one as a tan-colored solid (1.6 g).

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schering Aktiengesellschaft; US2005/90541; (2005); 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. 21857-45-4, name is 5-Methoxyindoline, A new synthetic method of this compound is introduced below., Computed Properties of C9H11NO

A solution of the product Step A (0.32 g; 2.14 mmol) in 48% HBr/ AcOH 1 :1 (10 ml) was refluxed overnight, then evaporated to dryness under reduced pressure. The residue was dissolved in EtOH (10 ml) and the solvent was removed under reduced pressure. This process was repeated three times and the residue was suspended in acetonitrile. The greyish solid formed was filtered off, washed with fresh CH3CN and dried to give a hydrobromide salt of the title compound (0.28 g; 60%). . 1 H-NMR (D2O ) 3.18 (tr, 2H, J = 7.8 Hz); 3.78 (tr, 2H, J = 7.8 Hz); 4.66 (HDO); 6.78 (d, 1 H, J = 8.6 Hz); 6.87 (s, 1 H); 7.23 (d, 1 H, J = 8.6 Hz).

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; AKAAL PHARMA PTY LTD; GILL, Gurmit, S.; GROBELNY, Damian, W.; WO2010/42998; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, 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 65435-04-3, Formula: C10H8ClNO2

A suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80 to 90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL ethanol. The solid was dissolved in 90 mL 2.5 N sodium hydroxide and stirred at 70 to 80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.

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-(2-Chloroacetyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6051593; (2000); A;,
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 1504-06-9 as follows. SDS of cas: 1504-06-9

To a Schlenk reaction flask with a volume of 20 mL, 0.2 mmol of 3-methyl-2-indanone, 0.4 mmol of morpholine, 0.04 mmol of I2, 0.4 mmol of H 2 O 2 and ethanol (2 mL) were added.The reaction flask was stirred at room temperature under an air atmosphere, and the progress of the reaction was monitored by TLC or GC until the reaction of the starting material was complete (8 hours).The reaction mixture after completion of the reaction was concentrated under reduced pressure, and the residue was purified by column chromatography (ethyl acetate / petroleum ether).

According to the analysis of related databases, 1504-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo University; Gao Lehan; Wei Wenting; Bao Wenhui; Xu Xudong; Wang Yining; (10 pag.)CN108440378; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl 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 6780-38-7, Recommanded Product: 6780-38-7

General procedure: To a stirred solution of the appropriate 3,4-dihydro-beta-carboline or 6,7-dihydrothieno[3,2-c]pyridine derivative (0.94 mmol) [0.20 g of 1-isopropyl-3,4-dihydro-beta-carboline (3), 0.20 g of 4-phenyl-6,7-dihydrothieno[3,2-c]pyridine (4)] and triethylamine (0.26 mL, 1.9 mmol) in dichloromethane (20 mL) was added a solution of 2-substituted acetyl chloride (1.9 mmol) [0.23 g of propionyl chloride (5a), 0.43 g of 2-(2,3-dichlorophenyl)acetyl chloride (5b), 0.32 g of 2-(dimethylamino)-acetyl chloride hydrochloride (5c), 0.58 g of 2-(1,3-dioxoisoindoline-2-yl)acetyl chloride (5d), 0.28 g of methoxyacetyl-chloride (5e), 0.44 g of phenoxyacetyl chloride (5f), 0.48 g of 2-(benzyloxy)acetyl chloride (5g), 0.36 g of 2-chloro-2-oxoethyl acetate (5h), 0.55 g of 2-(phenylthio)-acetyl chloride (5k), 0.29 g of 2-chloroacetyl chloride (5l)] in dichloromethane (5mL) at 0 C. The solution was stirred at 26 C until the starting material disappeared (20 min). The reaction mixture was washed with water (2¡Á10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (Merck 107736 Silica gel, 60H, CH2Cl2) to afford the products. 5.2.3 2-[10b-(1-Methylethyl)-2-oxo-1,2,4,5,5a,10,10a,10b-octahydroazeto[1′,2′:1,2]pyrido[3,4-b]indol-1-yl]-1H-isoindole-1,3(2H)-dione (1d) Yield 0.71 g (95%), white crystals, mp 208-210 C (MeCN). IR (KBr, cm-1): 3386, 1842, 1779, 1720, 1393, 1054. 1H NMR (DMSO-d6, 500 MHz): delta 10.73 (br s, 1H, NH), 8.00-7.97 (m, 2H, ArH), 7.96-7.92 (m, 2H, ArH), 7.51-7.49 (m, 1H, ArH), 7.48-7.47 (m, 1H, ArH), 7.18-7.14 (m, 1H, ArH), 7.05-7.02 (m, 1H, ArH), 5.04 (s, 1H, CH), 4.19-4.15 (m, 1H, CH2), 3.36-3.30 (m, 1H, CH2), 2.99-2.92 (m, 1H, CH2), 2.90-2.85 (m, 1H, CH2), 2.37 (sp, J=6.9 Hz, 1H, CH), 0.99 (d, J=7.2 Hz, 3H), 0.84 (d, J=6.8 Hz, 3H) ppm. 13C NMR (DMSO-d6, 125 MHz): delta 167.3 (C=O), 167.1 (C=O), 165.1 (C=O), 136.8 (C=), 135.5 (C=), 134.9 (HC=), 131.5 (HC=), 126.0 (C=), 123.5 (HC=), 122.1 (HC=), 118.9 (HC=), 118.1 (HC=), 112.0 (HC=), 109.8 (C=), 65.7 (C), 62.4 (N-CH), 36.9 (CH2), 33.1 (CH), 20.1 (CH2), 18.8 (CH3), 18.2 (CH3) ppm. HRMS calcd for C24H22N3O3 [M+H]+ 400.1656; found 400.1659.

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:
Article; Abranyi-Balogh, Peter; Mucsi, Zoltan; Csizmadia, Imre Gyula; Dancso, Andras; Keglevich, Gyoergy; Milen, Matyas; Tetrahedron; vol. 70; 51; (2014); p. 9682 – 9694;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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.

6-chloroindolin-2-one (8.35 g, 50 mmol) and 3-chloro-2-fluorobenzaldehyde (8.295 g, 52.5 mmol) were stirred at reflux for 6 hours in the presence of piperidine (1 ml). Then filter the reaction suspension, The collected solid was washed with methanol and dried to give (E)-6-chloro-3-(3-chloro-2-fluorobenzylidene)indol-2-one product (14.63 g, 47.5) as a yellow solid. Mmol), yield 95%.

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; Xiao Fei; Ma Jie; Ren Hongjun; Wang Wei; Xu Hongtao; Wang Meng; Zou Lihui; Ding Fei; Su Fei; (37 pag.)CN107698598; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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 169037-23-4, Recommanded Product: 169037-23-4

General procedure: The NiO-SiO2 catalyst (6.5 mol%) was added to a mixture of isatin (1 mmol), malononitrile (1 mmol), and 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol) in EtOH, and the reaction flask was placed in an oil bath and refluxed for the appropriate time. The progress of reaction was monitored by TLC. After the completion of the reaction, the heterogeneous catalyst was recovered from the reaction mixture by filtration. The filtrate was evaporated to afford the crude solid product which was later purified by column chromatography. The solid catalyst was washed with hot EtOH and then dried in oven to reuse.

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

Reference:
Article; Yagnam, Swetha; Akondi, Adinarayana Murthy; Trivedi, Rajiv; Rathod, Balaji; Prakasham, Reddy Shetty; Sridhar; Synthetic Communications; vol. 48; 3; (2018); p. 255 – 266;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem