Tag: M.W=100-200

Application of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-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.

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
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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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of Potassium 1,3-dioxoisoindolin-2-ide

Compound 4 (1.86g, 10mmol) and 1,6-b hexyl bromide (12.2g, 50mmol) in dry DMF (10 ml) and heated to 100 C, thermal insulation 12h. Then the excess is removed by reduced pressure distillation 1,6-b hexyl bromide. The silica gel column for separation and purification of the crude product (showering liquid is ethyl acetate/petroleum ether, volume ratio of 1:40), be 2.5g compound 5 (colorless powder), yield 81%.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hecheng Advanced Materials Co., Ltd; Kongxiang, Fei; Huang, Da; Wanggui, Xia; Liu, Canhui; Tan, Yudong; (22 pag.)CN105461628; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-1,3-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 3676-85-5, Computed Properties of C8H6N2O2

2.0 parts of a formyl derivative represented by the following formula (2) and 2.0 parts of 4-aminophthalimide represented by the following formula (3) are added to 20 parts of acetic acid and stirred at 40 C. for 6 hours The solution thus obtained was cooled to room temperature, poured into 50 parts of water, stirred for 30 minutes, and the precipitated solid was collected by filtration, washed with water and dried to obtain No. 1 of the above specific example. 1.5 parts of a methine compound (lambda max: 435 nm) represented by 1 was obtained.

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; NIPPON KAYAKU COMPANY LIMITED; TAKAHASHI, MASAYUKI; (14 pag.)JP2015/189767; (2015); A;,
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3676-85-5, name is 5-Aminoisoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H6N2O2

After 80 parts of water was added to 4- (manufactured by Tokyo Kasei Kogyo Co., Ltd.) amino phthalimide 16.2 parts, 0.4 parts of sodium hydroxide was added and dissolved.Under ice cooling, 35% aqueous sodium nitrite solution 19.7 parts was added, followed by 35% hydrochloric acid 26.2 parts was stirred for 2 hours and dissolved by adding little by little to obtain a suspension containing a diazonium salt.[0068]Then, 23.9 parts of 6-amino-4-hydroxy-2-naphthalenesulfonic acid was suspended in 100 parts of water, with sodium hydroxide, the pH was adjusted to 9.0.Here it was added dropwise by a pump over a period of suspension 15 minutes including the diazonium salt.After completion of the addition, to obtain a suspension of yellow by stirring for an additional 30 minutes.After stirring for 1 hour the suspension was stirred for 1 hour.The obtained filtered red solid was dried under reduced pressure at 60 C., to obtain a compound represented by formula (I-1) 40.5 parts.Measurement of the maximum absorption wavelength of this compound, lambdamax was 545nm.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company Limited; Ashida, Toru; (22 pag.)JP5831135; (2015); B2;,
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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 61-70-1 as follows. SDS of cas: 61-70-1

Add sodium hydride (60%, 1.4 g, 35.4 mmol) portionwise to the solution of 1-methylindolin-2-one (2.6 g, 17.7 mmol) in DMF (10 mL) at 0 C., stir for 30 min. Then add 1,2-dibromoethane (3.31 g, 17.7 mmol) to the mixture, stir the resulting mixture at room temperature overnight. Pour the reaction mixture to ice water, extract with ethyl acetate (100 mL*2), and wash the combined organic layers with brine (50 mL), dry over anhydrous sodium sulfate. Concentrate under reduced pressure, purify the residue by chromatography (silica gel, EtOAc_PE=1:3) to provide the title compound (1.5 g, 50.0%). MS: (M+1): 174.

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); A1;,
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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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of Indolin-2-one

5-Amino-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one 2-Oxindole (6.5 g) was dissolved in 25 mL of concentrated sulfuric acid and the mixture maintained at -10-15 C. while 2.1 mL of fuming nitric acid was added dropwise. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hour and poured into ice-water. The precipitate was collected by filtration, washed with water and crystallized from 50% acetic acid. The final crystalline product was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); 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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 7-Fluoro-1-methylindoline-2,3-dione

General procedure: To a mixture of 2-hydroxy-1,4-naphthoquinone (1 mmol), isatin (1 mmol) and CH3COOH10 mL, 5-aminotetrazole (1 mmol) was added. The mixture was stirred at reflux for an appropriatetime (Table 2). After completion of the reaction (TLC), the reaction mixture was cooled to roomtemperature and the solvent was evaporated under reduced pressure. Then, the crude product waswashed sequentially with 20 mL saturated NaHCO3 and 20 mL brine, purified by silica gel columnchromatography using petroleum ether: ethyl acetate (v:v = 1:1) as eluent to afford the pure product 4(the copies of all spectral data see Supplementary Materials).

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Liqiang; Liu, Yunxia; Li, Yazhen; Molecules; vol. 23; 9; (2018);,
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Electric Literature of 496-12-8, 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 496-12-8 as follows.

(1) Triethylamine (3.48 mL, 25.0 mmol) was added to a solution of isoindoline (4.98 g, 25.0 mmol) in chloroform (100 mL) at room temperature and the mixture was cooled in ice. Trichloroacetic acid chloride (2.79 mL, 25.0 mmol) was added dropwise thereto and the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1) to afford 2,2,2-trichloro-1-(1,3-dihydro-2H-isoindol-2-yl)ethanone as a purple powder (6.59 g).

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; BUSUJIMA, Tsuyoshi; OI, Takahiro; TANAKA, Hiroaki; SHIRASAKI, Yoshihisa; IWAKIRI, Kanako; SATO, Nagaaki; TOKITA, Shigeru; EP2687507; (2014); A1;,
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Electric Literature of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t. (2S,3?S)-tert-Butyl (1-Acetyl-1?-methyl-2?,3-dioxo-[2,3?-biindolin]-3?-yl)carbamate (3a)Yield: 165 mg (86%); colorless solid; mp 162-163 C; [alpha]D27 -21.4 (c0.5, CHCl3).HPLC: CHIRALPAK IB, n-heptane/EtOH (7:3), 1.0 mL/min, tR (major) =8.5 min, tR (minor) = 11.4 min, lambda = 230 nm; >20:1 dr; 99% ee.IR (ATR): 3307, 2962, 2641, 2322, 2083, 1919, 1902, 1811, 1771, 1709,1602, 1581, 1334, 755, 654 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.55 (m, 2 H, NH, ArH), 7.44 (d, J = 8.0Hz, 1 H, ArH), 7.25 (d, J = 8.0 Hz, 1 H, ArH ), 7.00 (td, J = 8.0, 4.0 Hz, 2 H,ArH), 6.90 (d, J = 8.0 Hz, 1 H, ArH), 6.59 (d, J = 4.0 Hz, 1 H, ArH), 6.51 (t,J = 8.0 Hz, 1 H, ArH), 5.12 (s, 1 H, CH), 3.17 (s, 3 H, NMe), 2.53 (s, 3 H,COCH3), 1.19 [s, 9 H, C(CH3)3].13C NMR (101 MHz, CDCl3): delta = 192.4, 172.8, 171.9, 153.6, 152.5,143.7, 136.4, 129.3, 126.5, 125.5, 124.7, 124.2, 123.6, 121.6, 117.3,108.0, 79.9, 69.4, 64.4, 28.0 (3 C), 26.2, 24.2.MS (ESI): m/z = 458.1 [M + Na]+.HRMS (ESI): m/z [M + Na]+ calcd for C24H25N3O5Na: 458.1686; found:458.1687.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
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Adding a certain compound to certain chemical reactions, such as: 7699-18-5, name is 5-Methoxyindolin-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 7699-18-5, Safety of 5-Methoxyindolin-2-one

General procedure: 4.4.6 (Z)-3-((2-(3-fluorophenyl)-1H-benzo[d]imidazol-6-yl)methylene)-5-methoxyindolin-2-one (5f) Compound 5f was prepared according to the method described for compound 5a, employing aldehyde 11b (120 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 111 mg, 0.83 mmol) to obtain the pure product 5f as a yellow solid (109 mg, 57%); mp: 196-198 C; IR (KBr): 3424, 3167, 2359, 2340, 1697, 1608, 1452, 1414, 1231, 1207, 1020, 840, 746 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.43 (bs, 1H), 8.29-8.22 (m, 2H), 7.99 (s, 1H), 7.79 (s, 1H), 7.76 (d, J = 8.4 Hz, 1H), 7.62 (d, J = 8.3 Hz, 1H), 7.44 (t, J = 8.8 Hz, 2H), 7.32 (d, J = 1.5 Hz, 1H), 6.89-6.72 (m, 2H), 3.62 (s, 3H); 13C NMR (75 MHz, DMSO-d6): delta 168.8, 164.9 and 161.6 (d, J = 248.4 Hz), 153.8, 152.0, 137.4, 136.4, 129.0 (d, J = 8.2 Hz), 128.3, 126.5, 125.9, 124.3, 121.9, 116.0 (d, J = 22.0 Hz), 14.6, 110.2, 108.6, 55.2; MS (ESI): m/z 386 [M + H]+; HRMS (ESI): calcd for C22H17O2N3F m/z 386.12946 [M + H]+; found 386.12993.

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-Methoxyindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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