Tag: M.W=100-200

Application of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-acetyl-2-oxindole as a brown solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.75 (s, br, NH), 7.83 (d, J=8 Hz, 1H), 7.78 (s, 1H, H-4) 6.88 (d, J=8 Hz, 1H),.3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

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

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1H, s), 10.32 (1H, s), 7.36 (1H, br. s), 7.35 (1H, s), 7.28 (3H, br. s), 6.59 (1H, s), 4.77 (2H, br. s), 4.71 (2H, br. s). MS: [M+H]+ 332/334.

The chemical industry reduces the impact on the environment during synthesis Isoindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-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. Formula: C8H4FNO2

A solution of 6-fluoroindoline-2,3-dione (2 g, 12.11 mmol) in dry DMF (100 ml) was cooled to 0 C., and NaH (60% w/w dispersion in mineral oil; 0.484 g, 12.11 mmol) was added portion wise over 10 minutes. The mixture was stirred at the same temperature for 10 minutes, then tert-butyl 2-bromoacetate (1.788 ml, 12.11 mmol) was added drop wise. The mixture was left warm to room temperature and stirred for 2 hours. DMF was evaporated under vacuum, and the crude was portioned between ethyl acetate (50 ml) and aqueous 1N HCl (40 ml). The aqueous phase was extracted with ethyl acetate (2¡Á50 ml), and the combined organic layers were dried over sodium sulfate, filtered and concentrate under vacuum. The crude was purified by flash chromatography on silica gel cartridge (petroleum ether:ethyl acetate=80:20) affording tert-butyl 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetate(2.21 g, 7.91 mmol, 65% yield).

The synthetic route of 6-Fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-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 16800-68-3, Product Details of 16800-68-3

3 – (2 – Fluorophenyl) propyne acid 4 – nitrophenyl-unitz (85.5 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 30 mg and gave rise 63% to unit_.

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Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 611-09-6, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 2 (200 mg, 1.04 mmol), neopentyl glycol (108 mg, 1.04 mmol), p-toluenesulfonic acid (25 mg, 145 mumol) were added to cyclohexane (10 ml), a water separator of the reaction device and a reflux condenser The reaction was refluxed for 16 h. The reaction produced a white solid insoluble in cyclohexane. The reaction was detected by TLC. The solid product was filtered, the solid product was washed with water, dried, and then subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1). The product was recrystallized from acetonitrile to obtain 243 mg of white needle crystals. Yield: 84%.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong University; Zhao Guisen; Zhang Zhen; Zhang Qian; Zhang Jingya; (39 pag.)CN110734391; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 5428-09-1, These common heterocyclic compound, 5428-09-1, name is 2-Allylisoindoline-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.

General procedure: Equimolar amounts of triethoxysilane and a respective aminated alkene were stirred with 330 ppm Cp2PtCl2 (i.e., 330 mumol per mol of silane) without solvent at 85 ¡ãC in a sealed schlenk tube under argon. After cooled to room temperature, the crude was purified by vacuum distillation or silica gel column chromatography to afford the desired product. The yield and the selectivity (i.e., the ratio of gamma-isomer/beta-isomer) were calculated on the basis of 1H NMR spectrum.

The synthetic route of 5428-09-1 has been constantly updated, and we look forward to future research findings.

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

Related Products of 1127-59-9,Some common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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: Isatin (0.5 g, 3.34 mmol) was added into a stirred solution ofKOH (0.56 g, 10.02 mmol) in ethanol 10 ml at 80 C. The reactionmixture was stirred at 0 C for 24 h. The mixture was added to50 g ice water. The pH was adjusted by the solution of 2 N HCl to4?5. The mixture was cooled overnight and filtered. The residuewas recrystallized by the mixture of petroleum/ethyl acetate(5:1). Compound 4 (0.8 g) was obtained and the yield was 96.87percent.

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

Reference:
Article; Liao, Chen; Liu, Yan; Liu, Chunxia; Zhou, Jiaqi; Li, Huilan; Wang, Nasi; Li, Jieming; Liu, Taiyu; Ghaleb, Hesham; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 845 – 854;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-37-8,Some common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, 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.

To the mixture of 6-chloro-2-oxindole (5.3 g, 32 mmol) (Crescent) and 3-chloro-4-fluorobenzaldehyde (5 g, 32 mmol) (Aldrich) in methanol (200 mL) was added piperidine (2.7 g, 32 mmol) (Aldrich) dropwise. The mixture was then heated at 50 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-4-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 8 g, 82%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chlorooxindole, its application will become more common.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 100510-65-4, These common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, 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.

To a’ -solution of 110 mg di-imidazol-1-yl-methanone and 6mg imidazole- in 2. ml tetrahydrofuran a solution of- 100 mg .6-amino-3,3-dimethyl-l, 3-dih’ydro-indol-2-one in. 1. mltetrahydrofuran was slowly added at 0C. After stirringat 0C’. for ‘3’0 minutes and 1 hour at room temperature 103mg . ” . 2-methyl-2-[(quinolin-4-ylmethyl)-amino]-propionicacid methyl ester were added and the reaction mixture was ,allowed to warm up to room temperature.. After 16 hours.stirring at .room ‘temperature the solution was heated for1 -hour -“at 70C.: After cooling to room temperature thesolvent of the mixture was removed .under reduced pressureand the residue was purified by preparative HPLC (C18reverse phase’?? column, ‘ elution ? with a water/ acetonitrile gradient with CL .%’? “trifluoroacetic acid). Lyop.hiliza.tion of the’-solution’yielded -a. white -solid, that was purified, .in addition.’by. flash chromatography on silica gel with a ‘d’ichloro-methane/methanol’ . gradient. The . fractions containing ‘the product? were’ combined and evaporated to yield ? – a . . white . solid.?Yield: 7.5 mg ‘ ?,?…M+H+ measured = ‘429 ‘1H-NMR (500 MHz’, ? DMSO/TMS).: d .= 10.50 (s, 1H) ; 8.87 (d,?1H); 8.25 (d, 1H) ; 8.09-(d, 1H) ; 7.82 (t, 1H) ; 7.70 (t,1H); 7.63 (d, 1H) ; 7.42 (d, IE).; 7.07 (d, 1H) ; 7.01 (s,1H); 5.14 (s, 2H); 1.43 (s, 6H); 1.29 (s, 6H)

The synthetic route of 100510-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVENTIS PHARMA S.A.; WO2006/10642; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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. SDS of cas: 3891-07-4

A solution of 126 (5 g, 26 mmol) in DMF (50 mL) was treated with sodium hydride (1.1 g, 32 mmol, 70 % dispersed in mineral oil) for 30 minutes at room temperature, followed by addition of BnBr (6.7 g, 39 mmol). After additional 1 hour, the reaction was quenched by water (200 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 10 % – 20 % ethyl acetate in petroleum ether to afford 127 as a white solid (4.8 g, 65 %).(ES, m/z) [M+H]+ 282.0; 1H NMR (300 MHz, CDC13) delta 7.85 – 7.88 (m, 2H), 7.71 – 7.74 (m, 2H), 7.25 – 7.31 (m, 5H), 4.55 (s, 2H), 3.95 (t, / = 6.0 Hz, 2H), 3.74 (t, / = 6.0 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3891-07-4, its application will become more common.

Reference:
Patent; ALECTOS THERAPEUTICS INC.; MERCK SHARP & DOHME CORP.; CHANG, Jiang; LIU, Kun; MCEACHERN, Ernest J.; MU, Changwei; SELNICK, Harold G.; SHI, Feng; VOCADLO, David J.; WANG, Yaode; WEI, Zhongyong; ZHOU, Yuanxi; ZHU, Yongbao; WO2012/62157; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem