Category: indolines-derivatives

Application of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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: The chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.19 (Z)-N-(4-Fluorophenyl)-2-(7-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (3-19) Yield 70percent; m.p.: 242-244 °C; yellow solid; 1H NMR (DMSO-d6, 400 MHz), delta 12.89 (s, 1H, NNH), 11.33 (s, 1H, NH), 10.84 (s, 1H, SCNH), 7.68-7.66 (m, 2H, J = 8.0 Hz, Ar2-H3 and Ar2-H5), 7.61 (d, 1H J = 7.2 Hz, Ar1-H4), 7.49-7.48 (m, 2H, J = 4.4 Hz, Ar2-H2 and Ar2-H6), 7.20 (d, 1H J = 7.2 Hz, Ar1-H6), 7.03 (t, 1H J = 7.6 Hz, Ar1-H5), 2.24 (s, 3H, CH3); 13C NMR (DMSO-d6, 101 MHz), delta 176.3, 163.1, 141.1, 137.4, 132.9, 132.7, 130.0, 128.2, 127.2, 122.3, 120.5, 119.4, 118.8, 15.8; IR: (KBr, nu/cm-1), 3308 (NN-H), 3165 (CON-H), 3052 (Ar-H), 1695 (-CONH-), 1625 (C=N), 1572 and 1539 (Ar-C=C), 1209 (C=S), 1153 (N-N); Elemental analysis calculated for C16H13FN4OS, C: 58.52, H: 3.99, N: 17.06, found C: 58.75, H: 3.66, N: 17.45.

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, Xu-Meng; Guo, Hui; Li, Zai-Shun; Song, Fu-Hang; Wang, Wei-Min; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 419 – 430;,
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Synthetic Route of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

(cis) 1-(1 /-/-Benzimidazol-2-ylmethyl)-1 ,2,3,4,4a,5,6,10b-octahydro-1 ,10- phenanthroline (0.045 g, 0.14 mmol), 2-(5-bromopentyl)-1 /-/-isoindole-1 ,3(2H)-dione (0.062 g, 0.21 mmol), potassium iodide (5 mg), and N,N-diisopropylethylamine (0.050 g, 0.31 mmol) in 3 mL of dimethylformamide were heated to 80 9C for 16 hours. The mixture was allowed to cool to room temperature and hydrazine (0.4 mL, 14.0 mmol) was added. The mixture stirred at room temperature overnight. The mixture was quenched with water and extracted 3 times with ethyl ether. The ether layers were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica chromatography eluting with a 0% to 10% gradient of 30% aqueous ammonium hydroxide in acetonitrile to yield 0.01O g (18%) of (cis)-5-[2-(3,4,4a,5,6,10b- hexahydro-1 ,10-phenanthrolin-1 (2/-/)-ylmethyl)-1 H-benzimidazol-1-yl]-1- pentanamine. 1H NMR (400 MHz, METHANOL-D4) delta ppm 1.0 (m, 2 H), 1.3 (m, 3 EPO H), 1.4 (s, 2 H), 1.6 (m, 1 H), 1.7 (m, 2 H)1 2.1 (m, 1 H), 2.3 (m, 2 H), 2.5 (m, 3 H), 2.8 (m, 1 H), 2.9 (m, 1 H), 3.1 (m, 1 H), 3.4 (s, 1 H), 3.5 (d, J=13.9 Hz, 1 H), 3.9 (m, 1 H), 4.1 (m, 1 H), 4.2 (d, J=13.9 Hz, 1 H), 7.2 (m, 2 H), 7.3 (m, 2 H), 7.5 (d, J=7.1 Hz, 1 H), 7.7 (d, J=7.9 Hz, 1 H), 8.4 (s, 1 H); MS m/z404 (M+1).

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 2518-24-3, name is 4-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

Step 1: Preparation of 4-amino-7-bromoisoindolin-1,3-dione (38) To a solution of 4-aminoisoindolin-1,3-dione (37) (0.5 g, 3.08 mmol) in MeOH (50 mL) was added a mixture of NBS (0.58 g, 3.24 mmol) as three portions at room temperature. Then, the mixture thus obtained was stirred at room temperature for 8 hours, and filtered. The filtrate was concentrated to give the crude product of 4-aminoisoindolin-1,3-dione 38 (0.42 g) as a solid, which was directly used in the next step without further purification.

The synthetic route of 2518-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GREEN CROSS CORPORATION; CHOI, Soongyu; PARK, Eun-Jung; SEO, Hee Jeong; KONG, Younggyu; SON, Ickhwan; MA, Sang-ho; CHA, Man-Young; KIM, Mi-Soon; PARK, Kisoo; (143 pag.)US2016/311772; (2016); A1;,
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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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(2-Oxopropyl)isoindoline-1,3-dione

Example 491; N-[7-(3-Fluoro-benzenesulfonyl)-1-methyl-1 ,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmeth isobutyramideStep 1 :2-(7-lodo-1-methyl-1 ,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl)- isoindole-1 ,3-dione To a mixture of 2-(6-iodo-benzofuran-3-yl)-ethylamine (2.00 g, 6.97 mmol) and 2-(2-oxo-propyl)- isoindole-1 ,3-dione (4.25 g, 20.9 mmol) was added trifluoroacetic acid (8.00 mL, 104 mmol) and then heated at 80 C . After 16 h, additional ketone (3 eq) was added and heating continued. After a total of 3 days, the reaction mixture was basified (DCM-aq. NaHC03) and the resulting precipitate was filtered, rinsed with DCM and dried to give an off-white solid, mp 302-304 C dec; MS m/z 473 [M + H]+.

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON, INC.; BACON, Edward R.; BAILEY, Thomas R.; DUNN, Derek D.; HOSTETLER, Greg A.; MCHUGH, Robert J.; MORTON, George C.; ROSSE, Gerard C.; SALVINO, Joseph M.; SUNDAR, Babu G.; TRIPATHY, Rabindranath; WO2011/87712; (2011); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 114041-16-6, 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 114041-16-6 as follows.

General procedure: Compound 8 (70.6 mg, 0.24 mmol) and 5,6-dimethoxyisoindoline(68.5 mg, 0.38 mmol) were dissolved in CH3CN (30 mL), followed by addition of K2CO3 (138.8 mg, 1.00 mmol). The mixture was heated under reflux and stirred at 90 C for 6 h. After cooling and filtration, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate/triethyamine) = 10:10:1, v/v/v) to afford 13(56.8 mg, 59%)

According to the analysis of related databases, 114041-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Liang; Ye, Jiajun; He, Yingfang; Deuther-Conrad, Winnie; Zhang, Jinming; Zhang, Xiaojun; Cui, Mengchao; Steinbach, Joerg; Huang, Yiyun; Brust, Peter; Jia, Hongmei; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3792 – 3802;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 15861-30-0, These common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, 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.

2, 3-Dihydro-1H-indole-5-carboxylic acid (12.4 mmol) was dissolved in DMF (5 mL) and 1, 2-dichloroethane (40 mL). DIPEA (12.4 mmol), 1- (3-dimethylaminopropyl)- 3-ethyl-carbodiimide hydrochloride (12.4 mmol), 1-hydroxybenzotriazole (12.4 mmol) and 2-aminothiazole (12.4 mmol) was added. Stirred at 50 C for 48h. HC1 (2M) (12.4 mmol) was added to the reaction mixture followed by water (30 mL). This gave a heavy precipitation which was removed by filtration. The solid was washed with water and 1,2-dichloroethane and dried. Yield: 56% 1H NMR (D6-DMSO) : 6.60 (s, 1H); 7.26 (d, 1H); 7.44-7. 54 (2H); 7.56 (d, 1H); 7. 86 (d, 1H); 8.45 (s, 1H) ; 11.51 (br s, 1H).

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2005/39572; (2005); A1;,
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 118289-55-7 as follows. category: indolines-derivatives

Example 1; Methylene chloride (200 ml) is added to 1-(1 ,2-Benzisothiazol-3- yl)piperazine (15 gm), stirred for 10 minutes and then triethylamine (22 ml) is added drop wise for 10 minutes. Trimethylsilyl chloride (15 ml) is added drop wise to the reaction mass for 20 minutes, tetrabutyl ammonium bromide (5 gm) is added and stirred for 1 hour at 25-300C. Then the reaction mass is heated to 400C and methylene chloride is distilled under vacuum. To this reaction mass sodium carbonate (16 gm) and 5-(2-chloroethyl)-6-chloro-oxindole (16 gm) are added, stirred for 10 minutes and added water (400 ml) and sodium iodide (2 gm). The contents are heated to 1000C and stirred for 7 hours 30 minutes at 95 – 1000C. Solid is filtered and slurried in 200 ml of water, filtered and washed with water (100 ml). Then the solid is slurried in isopropyl alcohol (75 ml) at reflux, refluxed for 1 hour and then filtered the solid at reflux point to give 15 gm of ziprasidone (HPLC purity: 98.36%).

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:
Patent; HETERO DRUGS LIMITED; WO2006/80025; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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. name: 7-Chloroisatin

General procedure: In sealed tube, a solution of 3 mL solvent (DMSO or DMF) of hydrazines 1 (0.5mmol), diketones 2 or 4 (0.5mmol), K2CO3 (1mmol), eosin Y (0.025mmol) was sequentially added. The reaction mixture was stirred under incandescent light (0.4 Wcm-2) irradiation at 45 °C for 24 h. Then, the mixture extracted with ethyl acetate (3 × 10 mL), and the organic layer was combined and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure, the residue was separated by flash column chromatography to afford the pure product 3 or 5 (PE: EA = 20:1).

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

Reference:
Article; Diao, Pinhui; Ge, Yanqin; zhang, Wenpei; Xu, Chen; Zhang, Nannan; Guo, Cheng; Tetrahedron Letters; vol. 59; 8; (2018); p. 767 – 770;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, SDS of cas: 6326-79-0

To a solution of 3a (150 mg, 0.66 mmol) in dry acetone (30 mL) was added Na2CO3 (anh. ) (1.0 g) and dimethylsulfate (0.8 mL) under Ar and the reaction mixture was heated at 60 C for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C). The solid residue was submitted to flash chromatography with CH2C12 to afford lla (140 mg, 0.58 mmol, 85%) (see Scheme 2 in Fig. 2B).

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; THE ROCKEFELLER UNIVERSITY; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; WO2005/41954; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 104618-32-8, 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 104618-32-8 as follows.

Hydrochloric acid (35%) (3.2 L) was added to a cooled solution of 4-aminobenzamide (2.0 Kg, 14.69 mol) in water (14 L, 7 volumes) at 5-100C. Then p-toluene sulphonic acid (10.1 Kg, 3.44 mol) was added to the reaction mixture and further cooled to -5C to -100C. Sodium nitrite (1.76 Kg, 25.7 mol) was dissolved into water (4 L, 2 volumes) and added to the cooled reaction mixture over a period of 2.5 hours at -5C to -100C and further stirred for 4 hours. Sodium sulphite (5.6 Kg, 44.4 mol) was dissolved into water (16 L, 8 volumes) and added dropwise to the diazonium salt over a period of 3 hours at a temperature of -5C to -100C. After stirring for 2 hours, the temperature of the reaction mixture was allowed to rise to ambient and stirred for 12 hours. The reaction was monitored by TLC. Methanol (16 L, 8 volumes) was added to the yellow suspension and 4-phthalimido- cyclohexanone (4.64 Kg, 19.07 mol) was added portionwise at a temperature of 40-450C. After maintaining the reaction mixture at 40-450C for 30 minutes, the temperature of the reaction mixture was raised to 70-750C and maintained for 8 hours. After completion of the reaction, the mixture was cooled to 25-300C, filtered and washed with water (40 L). The wet cake was mixed with water (40 L) and the pH adjusted to 7-8 using 10% potassium carbonate (aq) solution, and the slurry was filtered and washed with water (40 L). The product was dried under vacuum at 60-650C. The crude product was purified by reflux in dichloromethane (30 L) and dried to afford the title compound (3.70 Kg). Molar yield: 70%HPLC purity: 98.06%

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENERICS [UK] LIMITED; MYLAN INDIA PRIVATE LIMITED; GORE, Vinayak Govind; GADKAR, Maheshkumar; TRIPATHI, Anilkumar; MANKAR, Viraj; WO2010/122343; (2010); A1;,
Indoline – Wikipedia,
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