Category: indolines-derivatives

Related Products of 5332-26-3, The chemical industry reduces the impact on the environment during synthesis 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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, 2-(Bromomethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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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. 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. Recommanded Product: 16800-68-3

Step 1 : 2-(1-Acetyl-1 H-indol-S-yO-S-hydroxycyclopent^-enone. 1-Acetyl-1 ,2-dihydro-indol-3-one (7.0 g) is suspended in acetic acid (80 ml) and 1 ,3-cyclopentane-dione (3.92 g) is added. The reaction mixture is stirred for 20 min and triethylamine (5.56 ml) is added. The mixture is partitioned into 4 microwave vials and each portion is heated for 2 h at 1850C in the microwave. The reaction mixtures are recombined and concentrated in vacuo. The residue is treated with 2M methanolic hydrochloride solution (20 ml) and further methanol (5 ml) is added, until complete dissolution occurred. The solution is again concentrated in vacuo and the crude product is purified by flash chromatography (silica gel, eluting with ethyl acetate). The product is crystallized from ether / ethyl acetate 9:1 (v/v) to give 6.8 g (66%) of 2-(1-acetyl-1/-/-indol-3-yl)-3-hydroxycyclopent-2-enone.1H-NMR (200 MHz, CDCI3); delta = 2.31 (s, 3H), 2.55-2.82 (m, 5H), 7.19-7.59 (m, 4H), 8.43 (d, J = 7.5 Hz, 1 H).

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NYCOMED GMBH; BARTELS, Bjoern; WEINBRENNER, Steffen; MARX, Degenhard; DIEFENBACH, Joerg; DUNKERN, Torsten; MENGE, Wiro M.P.B.; CHRISTIAANS, Johannes A. M.; WO2010/15587; (2010); A1;,
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Reference of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-1,3-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.

General procedure: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
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Related Products of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

Step 1. Dimethyl (phthalimidomethyl)phosphonate (ii). A mixture of N-(bromomethyl) phthalimide (i) (10.43 g, 43.46 mmol) and trimethyl phosphite (5.93 g, 47.80 mmol) was heated at reflux in xylene (20 mL) for 6 h. The reaction mixture was then cooled to room temperature and concentrated. Crystallization from CHCl3hexane gave (ii) (7.60 g, 65%) as a white solid: 1H NMR (300 MHz, CDCl3) deltaH 3.84 (d, JH,P=10.8 Hz, 6 H), 4.12 (d, J=11.4 Hz, 2 H), 7.76 (m, 2 H), 7.87 (m, 2 H).

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; MethylGene, Inc.; US2004/82546; (2004); A1;,
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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. COA of Formula: C8H4KNO2

Potassium phthalimide (18.62 g, 0.10 mol) and tetrabutylammoniumbromide (TBAB, 5.00 g) were added to a solutionof 1,4-dibromobutane (35.5 mL, 0.30mol) in N, N-Dimethylformamide (DMF, 240 mL) at room temperature and then the mixture was stirred at 78 C for 6 h. After the completion of the reaction (monitored by TLC analysis), the mixture was filtered, and washed with DMF (20 mL × 2).The filtrate was evaporated under vacuum to removed DMF,the residual liquid was poured into ice-water bath, immediately a large amount of white solid generated. The white solid was collected by filtration, washed on the filter withwater and dried in vacuum. The crude residue was purifiedby recrystallization from methanol to afford pure N-(4-Bromobutyl) phthalimide 2 (23.60 g, 84%, m.p. 79-81oC aswhite solid. 1H NMR (CDCl3, 400 MHz), delta: 1.82-1.95 (m,4H, C13H, C14H), 3.45 (t, J=6.3 Hz, 2H, C15H), 3.73 (t,J=6.6 Hz, 2H, C16H), 7.27-7.74 (m, 2H, C3H, C6H), 7.83-7.86 (m, 2H, C1H, C2H); 13C NMR (CDCl3, 100 MHz), delta:27.3 (C13), 29.9 (C14), 32.8 (C15), 37.0 (C12), 123.3 (C3,C6), 132.1 (C4, C5), 134.0 (C1, C2), 168.4 (C7, C9). KunHu has reported the same compound in 2013 [17], the NMRcharacterization in the literature is described as follows: 1HNMR (CDCl 3, 500 MHz): d 1.84-1.94 (m, 4H), 3.45 (t,2H, J = 6.0 Hz), 3.73 (t, 2H, J = 6.5 Hz), 7.73 (dd, 2H, J =3.0, 5.5 Hz), 7.85 (dd, 2H, J = 3.0, 5.0 Hz); 13 C NMR(CDCl 3, 125 MHz): d 27.27, 29.89, 32.73, 36.99, 123.27,132.11, 133.99, 168.36.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1074-82-4, its application will become more common.

Reference:
Article; Shao, Yan-Dong; Song, Huang-Wang; Feng, Wen; Wang, Xiang-Hui; Shi, Zai-Feng; Wu, Lu-Yong; Chen, Guang-Ying; Lin, Qiang; Letters in Organic Chemistry; vol. 15; 3; (2018); p. 206 – 213;,
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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. 61-70-1, name is 1-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1-Methylindolin-2-one

To a 50 ml single-flask containing 10 ml water and 10 ml ethanol was added sodium hydroxide (10 mmol, 0.4 g). The reaction mixture was stirred until the solid dissolved. Then cooled to room temperature, indole-2-one (5.0 mmol) and benzaldehyde (5.5 mmol) was added. The reaction was stirred at room temperature for 2.0 hours. After addition of water (25 ml), the mixture was filtered and washed with water to give the desired products, yield: 85%.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lihong; Li, Zhanshan; Lu, Lianhong; Zhang, Wei; Tetrahedron; vol. 68; 5; (2012); p. 1483 – 1491;,
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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. 317-20-4, name is 7-Fluoroisatin, A new synthetic method of this compound is introduced below., Formula: C8H4FNO2

198 mg (1.2 mmol) 7-fluoroisatin, 144.1 mg (1.44 mmol) 2,4-pentanedione, 50 mL THF and 5 mL DMF as solvent, 1 mL H2O2, and 14.5 mg ZnCl2 as catalyst were added to a 100 mL round flask. The mixture was stirred and heated at 85 C. for 12 hours. The reaction was monitored with TLC. When TLC indicated that reaction was complete, heating was removed. The reaction mixture was concentrated, filtered, and washed with THF to obtain 175.5 mg desired product (compound 9), a yield of 59.2%. 1H-NMR (300 MHz, DMSO-d6) delta (ppm): 10.95 (1H, s), 7.59 (1H, d), 6.89 (1H, d), 6.75 (1H, t), 2.38 (3H, s), 2.24 (3H, s); 13C-NMR (75 MHz, DMSO-d6) delta (ppm): 164.2, 161.1, 153.6, 148.8, 129.9, 126.3, 117.4, 109.9, 106.3, 92.5, 23.9, 11.2; MS (ESI) for (M+H)+: 248.1.

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; SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY; Liang, Chengyuan; Tian, Danni; Jia, Minyi; (11 pag.)US10035808; (2018); B1;,
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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. 6341-92-0, name is 6-Chloroisatin, A new synthetic method of this compound is introduced below., Quality Control of 6-Chloroisatin

General procedure: Microwave Heating: diversity of substituted indoline-2,3-dione 2 (1.0 mmol) was introduced in a 10-mL Initiator reaction vial, diversity of substituent alpha-thiocyanatoethanone 1 (2.0 mmol), EtOH (1.0 mL), and sodium hydroxide (1.0 mmol, 0.040 g) were then successively added. Subsequently, the reaction vial was capped and then pre-stirred for 20 s. The mixture was irradiated (time: 10 min, temperature: 80 C; Absorption Level: High; Fixed Hold Time) until TLC (petroleum ether: acetic ether 3:1) revealed that conversion of the starting material 2 was complete. The reaction mixture was cooled to room temperature. Next, the system was diluted with cold water (20 mL) and neutralized by diluted acidic solution. The solid product was collected by Buechner filtration and was purified by recrystallization from 95% ethanol to afford the pure yellow solid (3a-z)

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xue; Wu, Qiong; Jiang, Bo; Fan, Wei; Tu, Shu-Jiang; Tetrahedron Letters; vol. 55; 1; (2014); p. 215 – 218;,
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Reference of 17702-83-9, These common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)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.

step 1 8-Morpholin-4-yloctylamine To a solution of N-(8-bromooctyl)phthalimide (8.46 g, 25.0 mmol) in CH3CN (70 mL) at room temperature wag added morpholine (4.80 g, 55.0 mmol). After 18 h at this temperature, the reaction mixture was concentrated and then diluted with EtOAc (100 mL). The organic layer was washed with 10percent aq. Na2CO3 (3*30 mL), H2O (2*20 mL), and brine (2*20 mL) and then dried (Na2SO4). After concentration, the residue was purified by the flash chromatography (5 to 10percent MeOH/CH2Cl2 gradient) to afford the substituted morpholine intermediate. To this substituted morpholine intermediate (7.40 g, 21.5 mmol) in MeOH (70 mL) at room temperature was added hydrazine monohydrate (1.28 mL, 25.8 mmol) and the resulting mixture was heated to reflux. After 2 h at this temperature, the reaction was concentrated and then diluted with 1N HCl (100 mL). The mixture was stirred for 1 h, and the precipitate that formed during this time was filtered and washed with excess 0.5 N HCl. The filtrate was basified with 50percent aq. NaOH (~7 mL) and stirred about 15 min. This aqueous solution was extracted with CHCl3 (4*50 mL) and the combined organic layers were washed with H2O (3*50 mL) and brine (1*50 mL). The organic layer was then dried (Na2SO4) and concentrated to afford the product (4.16 g, 77percent) as an oil; 1H NMR (DMSO-d6) delta81.18-1.34 (m, 12H), 1.34-1.43 (m, 2H), 2.21 (t, J=7.0 Hz, 2H), 2.26-2.33 (m, 4H), 2.46-2.52 (m, 2H), 3.53 (t, J=4.6 Hz, 4H); IR (film) 3390, 2930, 2860, 2820, 2790, 2710, 2180, 1640, 1610, 1460, 1390, 1375, 1360, 1320, 1300, 1275, 1200, 1135, 1120, 1080, 1040, 1010, 900, 870, 815, 800, and 725 cm-1; mass spectrum [(+) APCI], m/z 215 (M+H)+.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Butera, John A.; Caufield, Craig E.; Graceffa, Russell F.; Greenfield, Alexander; Gundersen, Eric G.; Havran, Lisa Marie; Katz, Alan H.; Lennox, Joseph R.; Mayer, Scott C.; McDevitt, Robert E.; US6214877; (2001); B1;,
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Synthetic Route of 3485-84-5,Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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 methyl 5-bromo-2-(propan-2-yloxy)pyridine-4-carboxylate (112a, 3.40 g, 12.4 mmol) and N-vinylphthalimide (2.58 g, 14.9 mmol) in toluene (124 mL) was added K2CO3 (5.19 g, 37.2 mmol) followed by Pd(P(tBu)3)2 (0.400 g, 0.775 mmol). The reaction mixture was degassed and heated in a sealed tube at 110 C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through CELITE. H2O (100 mL) was added, the organic layer was separated and concentrated under vacuum, and the residue was purified by column chromatography (0-80%, ethyl acetate/heptanes) to give methyl 5-[(E)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethenyl]-2-(propan-2-yloxy)pyridine-4-carboxylate (112b, 1.56 g, 34%) as yellow solid.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; EDWARDS, Martin Paul; KUMPF, Robert Arnold; KUNG, Pei-Pei; MCAPLINE, Indrawan James; NINKOVIC, Sacha; RUI, Eugene Yuanjin; SUTTON, Scott Channing; TATLOCK, John Howard; WYTHES, Martin James; Zehnder, Luke Raymond; US2014/179667; (2014); A1;,
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