Tag: M.W=200-300

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

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

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

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

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

Application of 15362-40-0,Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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.

To a four-necked flask was added compound IV (233 g, 0.84 mol), potassium hydroxide (94.3 g, 1.68 mol), 10% hydrochloric acid 668 mL, zinc hydroxide (167 g, 1.68 mol), and the temperature was raised to 85 C for 8 hours , Cooling to 60 ~ 65 , vacuum filtration, filter cake and add a small amount of water to get 499.5g (compound I: diclofenac zinc), the yield of 91%.

The synthetic route of 15362-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Liaoyuan Yinying Pharmaceutical Co., Ltd.; Li Guiying; Wang Zhaokun; Li Shumei; Peng Xiaojuan; Jin Xingtong; (8 pag.)CN106905178; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, name: N-(5-Bromopentyl)phthalimide

a) 4-[5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentyloxy]-benzoic acid methyl ester A mixture of 4-hydroxy-benzoic acid methyl ester (3.01 g, 19.8 mmol), 2-(5-bromo-pentyl)-isoindole-1,3-dione (3.9 g, 13.2 mmol), and K2CO3 (1.82 g, 13.2 mmol) in acetone (150 mL) was heated to reflux for 24 h. The reaction mixture was cooled to rt and the solvents were removed in vacuo. The crude was diluted in EtOAc and washed with 1N NaOH and brine. The organic layer was dried over sodium sulfate. The solvents were removed in vacuo. The crude was recrystallized from EtOAc to afford the title compound as a white solid (4 g, 83%). 1H-NMR (CDCl3): delta 7.95-7.98 (m, 2H), 7.83-7.86 (m, 2H), 7.70-7.73 (m, 2H), 6.86-6.89 (m, 2H), 4.00 (t, 2H, J=6.22 Hz), 3.88 (s, 3H), 3.73 (t, 2H, J=7.29 Hz), 1.82-1.89 (m, 2H), 1.73-1.81 (m, 2H), 1.50-1.57 (m, 2H).

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; Subasinghe, Nalin; Khalil, Ehab; Ali, Farah; Hufnagel, Heather Rae; Ballentine, Shelley; Travins, Jeremy M.; Leonard, Kristi A.; Bone, Roger F.; US2005/4031; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 87-48-9,Some common heterocyclic compound, 87-48-9, name is 5-Bromoindoline-2,3-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.

General procedure: The preparation was divided into two steps. Firstly, substituent indoline-2,3-dione (1 equiv) was dissolved in ethanol (10 mL), hydrazine hydrate (2 mL) was added. The reaction mixture was refluxed with magnetic stirring for 3 h and cooled to 0 C, then sodium hydroxide (3 equiv) was added, refluxed for 0.5 h and cooled to room temperature, then 150 mL water was added. The mixture was acidified by adding 2 N hydrochloric acid to pH 2, and extracted twice with dichloromethane. The organic filtrate was washed twice with brine, dried (Na2SO4), and then concentrated to give corresponding indolin-2-one by high-vacuum drying. Secondly, a mixture of the corresponding indolin-2-one (1 equiv) and furan-2-carbaldehyde (1 equiv) in ethanol was added two drops of piperidine and refluxed with magnetic stirring for 5 h. After the mixture cooled, the precipitate was filtered, washed with cold ethanol, dried, and recrystallized from methanol to afford the terminal product.

The synthetic route of 87-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhong, Ye; Xue, Mengzhu; Zhao, Xue; Yuan, Jun; Liu, Xiaofeng; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Xu, Yufang; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1724 – 1734;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 118289-55-7, 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 118289-55-7 as follows.

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem