Tag: M.W=100-200

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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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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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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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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., COA of Formula: C9H7NO3

2-Oxo-3-(4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrol-1-ylmethylene)-2,3-dihydro-1H-indole-5-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-5-carboxylic acid was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde to give the title compound. MS m/z 325.2 [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; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
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Reference of 32692-19-6, 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 32692-19-6 as follows.

To a solution of 5-nitroindoline (5.718 g) in DMF (60 mL) at 0C was sequentially added Nai l (1.348 g, 60% dispersion in mineral oil) and l-bromo-2-methoxyethane (5.368 g). The mixture was stirred at 0C for 2 h, and then was allowed to warm up to room temperature and stirred for another 3 h. At this point, TLC indicated the reaction to be complete. The reaction mixture was poured onto ice-water. The precipitate was collected, and re-dissolved in ethyl acetate. The organic layer was washed with water, brine and concentrated under reduced pressure to afford the desired product 1 (7.292 g, 94%, M+H+= 223.3) as a yellow solid.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACEA BIOSCIENCES INC.; XU, Xiao; WANG, Xiaobo; MAO, Long; ZHAO, Li; XI, Biao; WO2015/6754; (2015); A2;,
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These common heterocyclic compound, 50727-04-3, name is 5-Methoxyisoindoline-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. Quality Control of 5-Methoxyisoindoline-1,3-dione

A stirred solution of 4-methoxyphthalimide (21.3 g, 0.12 mol) in anhydrous tetrahydrofuran (425 ml) at 00C was treated dropwise with a solution of borane in tetrahydrofuran (1M1 340 ml, 0.34 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to 00C, methanol (150 ml) was added dropwise followed by 5M hydrochloric acid (150 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo, the mixture was diluted with water (750 ml) and was extracted with dichloromethane (3 x 750 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3 x 750 ml) and the combined extracts were evaporated to dryness in vacuo to afford 5-methoxyisoindoline (8.34 g, 47%) as a brown oil. 1H NMR (DMSOd6) 7.13 (1 H1 d), 6.84 (1H, d), 6.74 (1H1 dd), 4.05 (2H, s), 4.01 (2H, s), 3.73 (3H, s). MS: [M+H]+ 150.

The synthetic route of 5-Methoxyisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); 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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 7147-90-2

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added methylmagnesium chloride (3 M in THF, 20 mL) dropwise at 0 C. After the addition, the mixture was stirred at 0 C for 3 hours before it was quenched with satd. aq. NH4CI solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regioisomers (3.95 g, 100%). MS: 198.1 (M+H+).; Under N2 protection, triethylsilane (23 g, 200 mmol) and trifluoroboron etherate (8.51 g, 60 mmol) were added successively at -15 C to a mixture of 5-chloro-3-hydroxy-3-methyl- 2,3-dihydro-isoindol- 1 -one and 6-chloro-3-hydroxy-3-methyl-2,3-dihydro-isoindol- 1 -one (3.95 g, 20 mmol) in dry DCM (100 mL). Afterwards, the reaction mixture was stirred at room temperature for 2 hours and a saturated aqueous solution of NaHC03 (30 mL) was added. The mixture was then extracted with DCM and the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude mixture of products. The two regioisomers were separated by prep-HPLC to give the title compounds, 5-chloro-3-methyl-2,3-dihydro-isoindol-l-one (0.4 g, 11%) and 6-chloro-3- methyl-2,3-dihydro-isoindol-l-one (0.35 g, 9.6%) as white solids. MS: 182.0 (M+H+).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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