Tag: M.W=100-200

Reference of 2913-97-5, These common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)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.

Compound 2: NaBH(OAc)3 (3,05 g ;14,4 mmol) was added to a solution of N-ethylaniline (1,16 g ; 9,6 mmol) and 2-phthalimidoacetaldehyde (1) (2,72 g, 14,4 mmol) in CH2Cl2 (28 mL). After 24 h at 20°C, CH2Cl2 was added and the organic phase was washed with H2O, dried (MgSO4) and evaporated. The crude product was purified by chromatography over silica gel (80:20 CH2Cl2-cyclohexane) to afford 2 as a yellow solid (2,71 g, 96 percent). 1H NMR (250 MHz, CDCl3): delta 7,85 (m, 2H), 7,71 (m, 2H), 7.24 (t, J = 7,8 Hz, 2H), 6,86 (d, J = 7,8 Hz, 2H), 6.67 (t, J = 7,8 Hz, 1H), 3.91 (dd, J = 6,5, 8,1 Hz, 2H), 3,58 (dd, J = 6,5, 8,1 Hz, 2H), 3,46 (q, J = 6,9 Hz, 2H), 1.22 (t, J = 7,0 Hz, 3H). 13C NMR (63 MHz, CDCl3): delta 168,0 (C), 147,2 (C), 133,7 (CH), 131,8 (C), 129,2 (CH), 123,0 (CH), 116,0 (CH), 111,9 (CH), 47,8 (CH2), 44,6 (CH2), 35,0 (CH2), 12,2 (CH3). MS: m/z = 295 (MH+). Anal. calcd for C18H18N2O2 (294,14), C 73.45, H 6,16, N 9,52. Found C 73,33, H 6,17, N 9,62.

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universite Paris Descartes; EP2537855; (2012); A1;,
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Application of 3676-85-5, 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. 3676-85-5 name is 5-Aminoisoindoline-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.

Example 90 N-(2,6-Difluorobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (162 mg, 0.59 mmol, 1.2 eq) and triethylamine (60 mg, 0.59 mmol, 1.2 eq) were added to a solution of 2,6-difluorophenylacetic acid (101 mg, 0.49 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (80 mg, 0.49 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2.5 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate. The resultant crystal was washed with achloroform/methanol solution to give the title compound as a crystal (10 mg, 6.1%). MS m/z: 331 1H-NMR delta: 4.64 (2H, d, J = 4.64 Hz), 6.88 (1H, t, J = 5.73 Hz), 7.11 (2H, t, J = 8.05 Hz), 7.56 (1H, dd, J = 1.83, 8.29 Hz), 7.66 (1H, d, J = 8.29 Hz), 7.98 (1H, d, J = 1.71 Hz), 9.15 (1H, s), 11.08 (1H, s)

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

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
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Related Products of 39603-24-2, These common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-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.

Will be perchloric acid (70%, 1 mmol, 142 mg) was added 5-methoxyisatin (1 mmol, 177 mg), 2-amino-5-chloro-pyridine (1.35 mmol, 174 mg) And tert-butylisocyanide (1.35 mmol, 112 mg) in n-butanol (4 mL) The reaction was stirred at reflux for 8 hours. When the reaction solution was cooled to room temperature, Filtration and washing the filter cake with a small amount of ethanol gave the desired product in 39% yield.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong South China New Drug Initiative Center; Lin Shuo; Che Chao; Li Song; Yang Bo; Xin Shengchang; (18 pag.)CN105017253; (2017); B;,
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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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

5-Ethyl-2-oxindole To 5-Acetyl-2-oxindole (2 g) in 15 mL of trifluoroacetic acid in an ice bath was slowly added 1.8 g of triethylsilane; the reaction was then stirred at room temperature for 5 hours. One mL of triethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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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. 13220-46-7, name is 4-Methylindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 13220-46-7

1-(4-Methyl-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one 4-Methyl-1,3-dihydro-indol-2-one 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 295.2 [M++1].

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

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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These common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-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. category: indolines-derivatives

The 5-amino-isoindoline-one (Intermediate 8a, 2.1g, 14.2mmoL), acetone (3.5mL, 47.6mmoL) and sodium cyanide (2.1g, 46.8mmoL) was added to 90percent acetic acid (45mL) in.The addition was complete, stirred at room temperature for 48 hours.To the reaction mixture was added water (50mL) and ethyl acetate (100 mL), separated, the organic phase was washed with water (3 × 50 mL), saturated sodium bicarbonate (50 mL), water (50mL), dried over anhydrous magnesium sulfate , filtered, and the solvent was distilled off under reduced pressure, the residue was purified by flash column chromatography, eluent PE: EA = 1: 1, to give a white solid 2.7g, 88percent yield.

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

Reference:
Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
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Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
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Adding a certain compound to certain chemical reactions, such as: 3485-84-5, name is N-Vinylphthalimide, 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 3485-84-5, HPLC of Formula: C10H7NO2

General procedure: A magnetically stirred solution of the N-vinylphthalimide (173 mg, 1.00 mmol, 1.0equiv) and xanthate (408 mg, 1.50 mmol, 1.5 equiv) in ethyl acetate (2 mL) wasrefluxed for 15 min under a flow of nitrogen. DLP (10 mol %) was then added to therefluxing solution and the olefin was totally consumed in 90 min. The reactionmixture was then cooled down to room temperature, concentrated under reducedpressure and purified by flash chromatography on silica gel (Et2O/petroleum ether =1:2) to give the desired compound 8b as a white solid (419 mg, 0.94 mmol, 94%yield).

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:
Article; Huang, Qi; Qin, Ling; Zard, Samir Z.; Tetrahedron; vol. 74; 40; (2018); p. 5804 – 5817;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 1074-82-4, Product Details of 1074-82-4

Synthesis of the protected ketone monomer was conducted based on a modification of a previously reported protocol (50). Chloroacetone (10 mE, 12.5 mmol) and the potassium salt ofphthalimide (25.5 g, 13.8 mmol) were added to 150 mE of stirred dry acetone. The solution was then heated to 80 C. for 20 hours, after which it was cooled to room temperature and the acetone was removed in a rotary evaporator. The resulting solid was then redissolved in methylene chloride and washed repeatedly with water. The methylene chloride layer was dried over magnesium sulfate, filtered, and removed using a rotary evaporatot The resulting yellow crude solid was washed with diethyl ether several times until the solid became white; this solid was subsequently dried in a vacuum oven to yield purified intermediate A (Scheme 1A). Intermediate A (lOg, 50 mmol) was then added to 180 mE of toluene along with ethylene glycol (5.85 mE, 100 mmol) and dry para-tolenesulfonic acid (934 mg, 5 mmol) and refluxed for 15 hours. The reaction mixture was cooled to room temperature and the ethylene glycol layer was extracted three times with diethyl ether. The toluene and ether fractions were combined and washed three times with 5% (w/v) NaOH followed by deionized water. The organic layer was dried over magnesium sulfate and solvent was removed in a rotary evaporatot The crude was recrystallized from ethanol to yield pure intermediate B (Scheme 1B). Intermediate B was subsequently added to 100 mE of deionized water along with 15 g of NaOH and refluxed for 2 days, with an additional 60 g of NaOH added slowly over the course ofthe reflux. Afierwards, the reaction mixture was cooled to room temperature and extracted three times with 50 mE dichloromethane. The organic layers were then combined and dried over magnesium sulfate, filtered, and concentrated in a rotary evaporator to yield pure product C (Scheme 1C), a slightly yellow oil. Finally, the monomer was prepared by adding product C (21.1 mE, 180 mmol) to a 20% (w/v) NaOH solution (in water) containing 4-hydroxy TEMPO (10 mg, 0.06 mmol). This reaction mixture was brought to 0 C. in an ice bath and methacryloyl chloride (16.5 mE, 174 mmol) was added drop- wise over 2 hours under nitrogen flow. The ice bath was then allowed to warm to room temperature and the reaction left to stir overnight in darkness. Afier this time, stirring was halted and the product was allowed to collect at the top of the reaction flask. The pure monomer product (along with inhibitor) (shown in Scheme 1 D) was then isolated using a separatory funnel. The monomer was stored in the darkness at -20 C. until use. 1H NMR (600 MHz) in DMSO-d5: RNHCH2C(OCH2CH2O)CH3, 1.3 ppm, singlet, 3H;CH2CCH3CONHR?, 2 ppm, singlet, 3H; RNHCH2C(OCH2CH2O)CH3, 3.5 ppm, doublet, 2H; RNHCH2C(OCH2CH2O)CH3, 4 ppm, singlet, 4H; CH2CCH3CONHR?,5.35-5.65 ppm, doublet, 2H; CH2CCH3CONHR?, 6 ppm, sin-glet, 1H.

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; McMaster University; Hoare, Todd; Bakaic, Emilia; Smeets, Niels M.B.; Deng, Xudong; (55 pag.)US2016/151535; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., name: 5-Nitroindoline

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem