Author: Jessica.F

Synthetic Route of 41663-84-7, 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 41663-84-7 as follows.

EXAMPLE 7 A first 2-l oil-jacketed reactor with a bottom valve was equipped with a mechanical stirrer, Dean-Stark trap topped with a reflux condenser, and nitrogen supply means. It was charged with 260.8 g (1.265 moles) of 4-nitro-N-methylphthalimide, 473 ml of ODCB and 25 g (95 mmol) of HEGCl (dried from a brine solution as described hereinabove). The solution was heated to reflux and 100 ml of ODCB was removed with a nitrogen sweep. A second, similarly equipped 2-l oil-jacketed reactor was placed under the first reactor and charged with 124 g (1.265 mole) of potassium acetate and 293 ml of ODCB. This mixture was heated and ODCB removed in the same way. The contents of the first reactor were transferred over 10 minutes, with stirring, to the second via a transfer tube, with maintenance of the temperature at 1 85 C. Refluxing was observed and colorless oxides of nitrogen evolved; they turned brown upon exposure to air. Heating and stirring were continued for 6 hours, after which the mixture was allowed to cool and solids were removed over 4 hours by suction filtration through a fritted funnel. The solids so removed were washed twice with 100-ml portions of water and vacuum dried at 140 C., yielding the desired 4,4′-oxybis(N-methylphthalimide) in 71% yield.

According to the analysis of related databases, 41663-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; General Electric Company; US6028203; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, The chemical industry reduces the impact on the environment during synthesis 496-12-8, name is Isoindoline, I believe this compound will play a more active role in future production and life.

(Intermediate Example 89) 3-Amino-1-(1,3-dihydroisoindol-2-yl)-3-methylbutan-1-one 2,3-Dihydro-1H-isoindole (543 mg) and 3-amino-3-methylbutanoic acid (700 mg) were dissolved in N,N-dimethylformamide (30 ml). N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (876 mg) and hydroxybenzotriazole (698 mg) were added thereto at 0C, and then the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic phase was separated, and the aqueous phase was adjusted to pH 9 by adding a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated under reduced pressure to give the title compound (0.60 g, Y.: 60%) as a brown oily matter. 1H NMR; (CDCl3) delta (ppm): 1.2 (6H, s), 2.4 (2H, s), 4.7-4.8 (4H, m), 7.2-7.3 (4H, m). ESI/MS (m/z): 219 (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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; EP1595866; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 1074-82-4,Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, 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 100 ml two-necked round bottom flask, 5.08 g phthalimide potassium salt (27.4 mmol) and 30 ml allylbromine (26.6 mmol) were dissolved in 40 ml DMF under the nitrogen atmosphere. The mixture was stirred for half an hour at 55 ¡ãC for 17 h, then 200 ml H2O was added and the mixture was?extracted with CH2Cl2 (80 ml ¡Á 3). The combined organic phase was dried over anhydrous Mg2SO4. After the removal of solvent under reduced pressure, the crude product was purified by column chromatography on silica gel with CH2Cl2 as the eluent, the collected pale?yellow oil was determined to be the desired product 2-allylisoindoline-1,3-dione (4.87 g, 95percent yield). 1H NMR (400 MHz, CDCl3): delta 7.90 (m, 2H), 7.76 (m. 2H), 5.93 (m, 1H), 5.26 (m, 2H), 4.34 (d, J = 8.0 Hz, 2H). 13C NMR (101 MHz, CDCl3): delta 167.95, 134.04, 132.26, 131.67, 123.37, 117.84, 40.14.

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

Reference:
Article; Wu, Huarui; Zheng, Chaoyue; Chen, Naiwu; Zhu, Jie; Gao, Deqing; Tetrahedron Letters; vol. 58; 16; (2017); p. 1576 – 1578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[0590] Procedure: To a stirred solution of 4-chloro-7-methoxyquinoline (0.05 g, 0.25 mmol) in 1,4- dioxane (5 mL) were added 5-nitroindoline (0.046 g, 0.28 mmol), cesium carbonate (0.25 g, 0.77mmol) and Xanthphos (0.029 g, 0.051 mmol). The resulting mixture was purged with argon for 15 min and added Pd2(dba)3 (0.023 g, 0.025 mmol) was added and the mixture was purged for another 10 min. Resulting mixture was stirred for 16h at 100 C. Progress of the reaction was monitored by TLC. Reaction mixture was filtered through celite bed and filtrate was diluted with ethyl acetate (20mL), washed with water (2 x 10mL) followed by brine (10 mL), dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude was purified by combiflash using 55-60% ethyl acetate in hexane to afford 7-methoxy-4-(5-nitroindolin-1-yl)quinoline as yellow solid (0.12 g, 75%).1HNMR (400 MHz, DMSO-d6): delta 8.83 (d, J = 4.4 Hz, 1H), 8.08 (s, 1H), 7.91-(d, J = 8.8 Hz, 1H), 7.73 (d, J = 9.2 Hz, 1 H), 7.46 (s, 1H), 7.36 (d, J = 4.8 Hz, 1H), 7.23 (d, J = 9.2 Hz, 1H), 6.24 (d, J = 8.8 Hz, 1H), 4.26 (t, J = 8.4 Hz, 2H), 3.93 (s, 3H), 3.32 (t, J = 8.4 Hz, 2H); LCMS (ES) m/z = 322.1 [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, 5-Nitroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MAVUPHARMA, INC.; GALLATIN, William Michael; ODINGO, Joshua; DIETSCH, Gregory N.; FLORIO, Vincent; VENKATESHAPPA, Chandregowda; DURAISWAMY, Athisayamani Jeyaraj; (273 pag.)WO2019/46778; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 25369-33-9,Some common heterocyclic compound, 25369-33-9, name is 7-Chloroindolin-2-one, molecular formula is C8H6ClNO, 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: DMF-DMA (2.66 mL, 20.0 mmol) was added to a solution of the appropriate indole (0.78 mmol) in toluene (3 mL). The mixture was stirred for 2-4 h. The precipitate was collected by filtration and washed with dichloromethane.

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

Reference:
Article; Praveen Kumar; Gut, Jiri; Guedes, Rita C.; Rosenthal, Philip J.; Santos, Maria M.M.; Moreira, Rui; European Journal of Medicinal Chemistry; vol. 46; 3; (2011); p. 927 – 933;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 169037-23-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 169037-23-4 name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 133-(1 ,4′-bipiperidin-1 ‘-ylmethyl)-//-(1 -phenylcvclopropyl)-6-r(trifluoromethyl)oxyl-2-r3- (trifluorometh l)phenyll-4-quinolinecarboxamide3-methyl-6-r(trifluoromethyl)oxyl-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxylic acidTo a suspension of 5-[(trifluoromethyl)oxy]-1 /-/-indole-2,3-dione (5.0 g, 21 .63 mmol) in ethanol (50 mL) was added a solution of potassium hydroxide (7.28 g, 130 mmol) in water (20.00 mL) slowly. 1 -[3-(Trifluoromethyl)phenyl]-1 -propanone was added (4.37 g, 21.63 mmol) and the mixture was heated to reflux for 1 h. The ethanol was removed under reduced pressure and the residue was dissolved in water and washed with diethyl ether. The aqueous mixture was chilled and adjusted to pH 3 with concentrated HCI. The solid was collected by filtration, washed with H20, and air dried to afford 3-methyl-6- [(trifluoromethyl)oxy]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (8.5 g, 95% yield). MS (m/z) 416.1 (M+H+).

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:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M; HILFKER, Mark, A.; MANAS, Eric, S.; YE, Guosen; WO2011/119704; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3¡Á30 mL). The combined organic layer washed with H2O (2¡Á10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 41910-64-9, 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 41910-64-9 as follows.

General procedure: 5.1.25. 7-Fluoro-5-(methylsulfanyl)-2,3-dihydro-1H-indole (16f) To a stirred solution of potassium thiocyanate (14.0 g, 145 mmol) in MeOH (150 mL) was added bromine (3.80 mL, 72.3 mmol) dropwise at 0 C under N2 atmosphere. After the mixture was stirred for 15 min, a solution of compound 15f (9.00 g, 65.7 mmol) in MeOH (100 mL) was added and the resulting mixture was stirred at room temperature for 3 h. A solution of potassium hydroxide (18.4 g, 329 mmol) in water (120 mL) was added slowly to the mixture followed by stirring at 43 C for further 30 min. The reaction mixture was cooled to 10 C, and then iodomethane (4.10 mL, 65.7 mmol) was added. The resulting mixture was stirred at room temperature for 30 min. After the mixture was concentrated under reduced pressure, the residue was partitioned between CH2Cl2 and water. The organic layer was separated, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/CH2Cl2 = 2/1 to 1/1) to give the title compound (2.80 g, 23%). 1H NMR (400 MHz, CDCl3) delta 2.42 (3H, s), 3.05 (2H, t, J = 8.4 Hz), 3.62 (2H, t, J = 8.4 Hz), 6.85 (1H, d, J = 10.8 Hz), 6.93 (1H, s).

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sato, Kenjiro; Sugimoto, Hiromichi; Rikimaru, Kentaro; Imoto, Hiroshi; Kamaura, Masahiro; Negoro, Nobuyuki; Tsujihata, Yoshiyuki; Miyashita, Hirohisa; Odani, Tomoyuki; Murata, Toshiki; Bioorganic and Medicinal Chemistry; vol. 22; 5; (2014); p. 1649 – 1666;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5428-09-1, 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 5428-09-1 as follows.

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3.x.20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

According to the analysis of related databases, 5428-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 104618-32-8, These common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, 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.

Example 8 3-Amino-6-methoxycarbonyl-1,2,3,4-tetrahydrocarbazole oxalate Reaction of 4-phthalimidocyclohexanone (0.37 g) with 4-ethoxycarbonylphenylhydrazine hydrochloride (0.33 g), and subsequent deprotection by the method described in example 3, gave the title compound free base. This was converted to the oxalate salt (0.11 g), mp 230-240C dec.

The synthetic route of 104618-32-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem