Month: June 2021

Application of 603-62-3,Some common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, 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 solution of potassium hydroxide (16.1 g, 286 mmol) in water (500mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspensionwas stirred at 0 C for 3 hrs, and then heated to 30 C for 3 hrs. To the solution, was addedHC1 (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hr. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3-nitro-phthalamic acid as awhite solid (24.6 g, 90% yield): ?HNMR(DMSO-d6) 5 7.69 (brs, 1H, NHJ]), 7.74 (t, J 8 Hz, 1H, Ar), 7.92 (dd, J= 1, 8Hz, 1H, Ar), 8.13 (dd, J= 1, 8Hz, 1H, Ar), 8.15 (brs, 1H, NHJ]), 13.59 (s, 1H, 01]); ?3CNIVIR(DMSO-d6)5 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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

Reference:
Patent; CELGENE CORPORATION; HAGNER, Patrick; GANDHI, Anita; POURDEHNAD, Michael; (67 pag.)WO2017/96024; (2017); 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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
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 3676-85-5 as follows. HPLC of Formula: C8H6N2O2

15 g of 5-aminophthalimide was added to 105 g of water and to this mixture, 39 g of a 35% aqueous hydrochloric acid was added dropwise. The reaction was kept at temperatures no higher than 5C and 48.7 g of a 16% aqueous sodium nitrite was added dropwise. Thereafter, the reaction was kept at temperatures from -2 to 2C for 120 minutes with stirring and the insoluble matter was removed by suction filtration to give an aqueous 5-diazophthalimide chloride.

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo; EP1650267; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1504-06-9, 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. 1504-06-9, name is 3-Methyloxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an open-air tube at room temperature (25 C), the corresponding 3-substitutedoxindole (0.15 mmol) was added to a solution of organocatalyst 5 (10 mol%) in toluene (1 mL). After 5 minutes, the mixture was introduced into a cooling bath at 0 C, andafter two minutes di-tert-butylazodicarboxilate (0.11 mmol, 1.1 eq.) was added in oneportion. The reaction was then allowed to react for 3 days. After this time, water (5 mL)and ethyl acetate (5 mL) were added, and the aqueous layer was then re-extracted twice (2 x 10 mL). The combined organic phases were dried (MgSO4) and evaporated underreduced pressure. Finally, the reaction crude was purified by column chromatographyon silica gel or TLC preparative using hexane/ethyl acetate mixtures as eluent. Spectroscopic data are listed within the article.

The synthetic route of 3-Methyloxindole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Benavent, Lloren; Baeza, Alejandro; Freckleton, Megan; Molecules; vol. 23; 6; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 15362-40-0, 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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The material 2,6-dichlorodiphenylamine (IV) (15mmol, 3.572g) was dissolved in 50ml toluene solvent and added to a three-necked flask, chloroacetyl chloride (16.5mmol, 1.8637g) was added dropwise, heated to 120 , Stir the reaction for 3h,TLC detected that the reaction of 2,6-dichlorodiphenylamine (IV) was completed and cooled to room temperature. [Et3NH]Cl-AlCl3 (30mmol, 8.129g) was slowly added dropwise to the reaction solution, stirred at room temperature for 30min, the oil bath was heated to 60C, and the reaction was stirred for 4h.TLC monitoring until the N-phenyl-N-(2,6-dichlorophenyl)chloroacetamide (III) intermediate disappeared, the reaction solution was slowly poured into a separatory funnel, allowed to stand for separation, and the ions were separated The liquid is recovered and applied. The application effect is shown in Table 1. The organic layer is added dropwise with 10% NaOH (30mmol, 1.2g) and heated to reflux for 2h.TLC monitors the completion of the reaction of 1-(2,6-dichlorophenyl)-2-indoline (II) intermediate, separates and removes the organic layer, evaporates part of the water from the water layer under reduced pressure, cools and crystallizes, Recrystallized with water,4.035g of white solid was obtained with a yield of 84.56%,The HPLC content is 99.85%.

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University of Technology; Luo Shuping; Xu Dandan; Ren Chenchao; Wang Tianqi; (6 pag.)CN111116391; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 150544-04-0, 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. 150544-04-0, name is 6-Aminoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

6-(Morpholin-4-yl)-2-oxindole 6-Amino-2-oxindole (2.2 g), 4.0 g 2,2′-dibromoethyl ether and 7.9 g sodium carbonate were refluxed in 20 ml ethanol overnight, concentrated and diluted with 50 ml of water.. The mixture was extracted three times with 50 ml of ethyl acetate and the organic extracts combined, washed with 20 ml of brine, dried over anhydrous sodium sulfate and concentrated to dryness.. The solid was chromatographed on a column of silica gel (ethyl acetate:hexane (1:1) containing 0.7percent acetic acid) to give 1.2 g (37percent yield) of the title compound as a beige 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, 6-Aminoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 60434-13-1, name is 5-Chloro-1-methylindoline-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 60434-13-1, SDS of cas: 60434-13-1

General procedure: A solution of N-methylisatin (81 mg, 0.5 mmol), phenylacethylene (77 mg, 0.75 mmol), CuI (19 mg, 0.1 mmol), and Cs2CO3 (245 mg, 0.75 mmol) in CH3CN (1.0 mL) was stirred at room temperature for 18 h. After aqueous extractive work up and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow soild, 81 mg (61%). Other compounds were prepared similarly, and the spectroscopic data of unknown compounds 1b, 1d, and 1e are as follows.

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-Chloro-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Roh, Hwa Jung; Lim, Jin Woo; Ryu, Ji Yeon; Lee, Junseong; Kim, Jae Nyoung; Tetrahedron Letters; vol. 57; 38; (2016); p. 4280 – 4283;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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.

7-fluoro-3-(hydroxyimino)indoline-2-one7-fluoroindoline-2,3-dione (5 g, 30.28 mmol) was taken up in ethanol (70 mL). Hydroxylamine hydrochloride (3.13 g, 45.04 mmol) was added in one portion and this mixture was heated in a 105 C. oil bath. Reflux at that temperature was continued for 2.5 hours. The mixture was cooled to room temperature and poured into 5 times its volume of water. The resulting yellow precipitate was filtered and washed with water. This solid was dried at 70 C. under vacuum. Reducing the volume of filtrate in a rotoevaporator and allowing the liquor to stand overnight at room temperature formed a second crop. The resulting solid was filtered and washed with water. This second sample was dried at 70 C. under vacuum. These two crops were combined to afford the 7-fluoro-3-(hydroxyimino)indoline-2-one as a yellow solid (4.19 g, 23.26 mmol, 77% yield). 1H NMR (500.333 MHz, DMSO) delta 13.50 (s, 1H), 11.18 (s, 1H), 7.80 (d, J=7.5 Hz, 1H), 7.29 (dd, J=9.2, 9.4 Hz, 1H), 7.04 (m, 1H). MS APCI, m/z=181 (M+H). HPLC 1.20 min.

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

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 446292-07-5,Some common heterocyclic compound, 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, molecular formula is C21H21N3O5, 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 1 : Preparation of 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-l,3-oxazolidin- 5-yl}methyl)-lH-isoindol-l,3(2H)-dione, the compound of formula I(2R)-2-Hydro y-3-[4-(3-oxo-4-mophiholinyl)phenyl]amino-propyl-lH-isoindol-l ,3(2H)- dione (10.0 g; 25 mmol), the compound of formula III, containing 1.0 % of the (2S)-isomer was charged into a flask and tetrahydrofuran (200 ml) was added. NN-carbonyldiimidazole (4.1 g; 25 mmol) was added to the stirred mixture. The mixture was heated up to boil and refluxed for 5 hours.The white suspension was cooled to the temperature of 20C, stirred for 1.5 hours, aspirated and washed with tetrahydrofuran (50 ml). The product was poured into a flask with 2- methoxyethanol (175 ml). The mixture was heated up to boil and stirred until dissolution. Active carbon (0.5 g) was added to the solution and filtered off while hot after 10 minutes and washed with 2-methoxyethanol (10 ml). The solution was cooled to the laboratory temperature and stirred for 1 hour. The resulting crystals were aspirated and washed with methanol (100 ml). The aspirated product was dried in a vacuum drier at a temperature up to 60C. 9 g (85 % of theory) of 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-l ,3-oxazolidin-5-yl} methyl)- lH-isoindol- l ,3(2H)-dione with the isomeric purity of 99.98% were obtained, HPLC purity 99.7%, m. p. = 221 – 223 C. The polymorphous structure of the compound (I) was also characterized with the X-ray powder diffraction (Fig. 1) with the characteristic 2 theta angles 4.63; 12.00; 13.9; 15.3; 15.87 and 24.55.

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

Reference:
Patent; FARMAK, A.S.; URBASEK, Miroslav; HRADIL, Pavel; GREPL, Martin; FIALOVA, Petra; OREMUS, Vladimir; SLEZAR, Petr; WO2012/41263; (2012); A2;,
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. 954-81-4, name is N-(5-Bromopentyl)phthalimide, A new synthetic method of this compound is introduced below., name: N-(5-Bromopentyl)phthalimide

To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%). ?H NMR (400 MHz, CDC13): 7.84 (dd, J= 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J 7.3 Hz, 2H), 2.85 (t, J 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M+1).

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; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LEWIS, Michael; (300 pag.)WO2018/98204; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem