Tag: M.W=100-200

Some common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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

Under argon atmosphere conditions, add 0.0133 g (0.10 mmol) of 2-methylindolinoline (1a), 0.0013 g (0.002 mmol) of acid eosin EosinY, 0.150 g of Antarctica lipase CAL-A, 0.0146 g (0.10 mmol) of n-octyl mercaptan, 0.104 g (0.50 mmol) of allyl-3-methoxyphenyl carbonate (2b), methyl tert-butyl ether (TBME) 2.0 mL;The reaction was stirred at 45 C for 6 hours under a 6w white light. After the reaction, the insoluble enzyme was removed by suction filtration, the solvent was distilled off under reduced pressure, and the solvent was separated by column chromatography. The eluent: (V) petroleum ether / (V) Ethyl acetate = 30/1. 0.0189 g of a yellow liquid product (3ab) was obtained with a product yield of 87%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6872-06-6, its application will become more common.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (16 pag.)CN110437123; (2019); A;,
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Synthetic Route of 39603-24-2, A common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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 25 ml round bottom flask, a mixture of isatin / acenaphthoquinone / 2-hydroxynaphthoquinone/ ninhydrin (1 mmol), o-phenylene diamine (1 mmol) in ethanol (95 %, 10 mL) and sulfamic acid (20 mol %) was added. The reaction mixture was stirred at ambient temperature for time mentioned in Table II, monitored by TLC. After completion of reaction, the mixture was filtered washed with ethanol and dried to furnish the desired pure products in high yields.

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

Reference:
Article; Hegade, Pravin G.; Mane, Mansing M.; Patil, Jayavant D.; Pore, Dattaprasad M.; Synthetic Communications; vol. 44; 23; (2014); p. 3384 – 3391;,
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Reference of 550-44-7, 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. 550-44-7, name is 2-Methylisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of magnesium (1.0 M in THF, 22 mL, 23.8 mmmol) was added 4-bromo-1-butene (2.2mL, 22 mmol) under a nitrogen atmosphere. After stirring the mixture for 30 min, the resultingsolution was added to the solution of N-methylphthalimide (1.42 g, 6.38 mmol) in THF (34 mL) at-20 C and stirred for additional 1 hour at the same temperature. The reaction was quenched byaddition of saturated aqueous NH4Cl (20 mL), and the resulting solution was extracted with EtOAc(30 mL). The organic extracts were washed with brine (20 mL), dried over Na2SO4, filtered, andconcentrated in vacuo to give a crude material (1.61 g). To a solution of the crude material (1.61 g) in dichloromethane (68 mL) was added triethylsilane (4.3mL, 27 mmmol) and boron trifluoride diethyl ether complex (3.4 mL, 27 mmol) under a nitrogenatmosphere at -20 C. The mixture was allowed to warm to 0 C and stirred for 30 min. The reactionwas quenched by addition of saturated aqueous NaHCO3 (50 mL). The resulting solution wasextracted with EtOAc (60 mL). The organic extracts were washed with brine (50 mL), dried overNa2SO4, filtered, and concentrated in vacuo to give a crude material. This material was purified bycolumn chromatography (silica gel, hexane/EtOAc = 3/1 to 1/1) to give 3a (1.17 g, 5.81 mmol, 85%for 2 steps) as a pale yellow oil. Rf = 0.32 (silica gel, hexane/EtOAc = 1/1); 1H NMR (300 MHz, CDCl3) delta 7.83 (d, J = 6.6 Hz, 1H, ArH), 7.56-7.41 (m, 3H, ArH), 5.70 (ddt, J = 6.3, 10.5, 17.1 Hz, 1H, CH),4.97-4.90 (m, 2H, CH2), 4.53 (t, J = 4.2 Hz, 1H, CH), 3.11 (s, 3H, CH3), 2.13-2.00 (m, 2H, CH2), 1.80 (m, 1H,CH2), 1.60 (m, 2H, CH2); 13C NMR (75 MHz, CDCl3) delta 168.5 (C), 144.6 (C), 137.1 (CH), 132.7 (C),131.2 (CH), 128.0 (CH), 123.4 (CH), 121.9 (CH), 115.1 (CH2), 60.9 (CH), 29.7 (CH2), 27.2 (CH3),26.6 (CH2).

The synthetic route of 2-Methylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sengoku, Tetsuya; Nagai, Yuichiro; Inuzuka, Toshiyasu; Yoda, Hidemi; Synlett; vol. 30; 2; (2019); p. 199 – 202;,
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Related Products of 150560-58-0,Some common heterocyclic compound, 150560-58-0, name is 5-Isopropylindoline-2,3-dione, molecular formula is C11H11NO2, 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 based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL×4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Isopropylindoline-2,3-dione, its application will become more common.

Reference:
Article; Javid, Muhammad Tariq; Rahim, Fazal; Taha, Muhammad; Nawaz, Mohsan; Wadood, Abdul; Ali, Muhammad; Mosaddik, Ashik; Shah, Syed Adnan Ali; Farooq, Rai Khalid; Bioorganic Chemistry; vol. 79; (2018); p. 323 – 333;,
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Related Products of 13220-46-7, A common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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.

5-Chloro-4-methyl-2-oxindole A suspension of 3.0 g of 4-methyl-2-oxindole was stirred in 50 mL of acetonitrile at room temperature while 3.3 g of N-chlorosuccinimide was added in portions. Trifluoroacetic acid (1 mL) was then added. The suspension was stirred at room temperature for 3 days during which time solid was always present. The white solid was collected by vacuum filtration, washed with a small amount of cold acetone and dried overnight in a vacuum oven at 40 C. to give 2.5 g (68%) of 5-chloro-4-methyl-2-oxindole.

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

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Synthetic Route of 1074-82-4,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.

To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 mm at room temperature. After complete addition, the reaction mixture was stirred at 90C for 1 8 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered anad concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield).H NMR (400 MHz, CDCI3): d 7.82 (dd,J= 5.5, 3.1 Hz, 2H), 7.69 (dd,J= 5.5, 3.0 Hz, 2H),3.68 (t, J= 7.2 Hz, 2H), 3..38 (t, J= 6.8 i-iz, 2Ff). 1.93-1.85 (n:i, 2H), 1.70 (p, J= 7,5 Hz, 2H),1.53-1.43 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Potassium 1,3-dioxoisoindolin-2-ide, its application will become more common.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; SHIRUDE, Pravin S.; (258 pag.)WO2017/6282; (2017); 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. 56341-37-8, name is 6-Chlorooxindole, A new synthetic method of this compound is introduced below., Safety of 6-Chlorooxindole

A mixture of 750 ml of dichloromethane, 150 g of 6-chlorooxindole, 161.6 g of chloroacetyl chloride and 477.2 g of aluminium chloride was refluxed for 9.5 hours. The reaction mass was quenched into a mixture of crushed ice and 135 ml of hydrochloric acid. The formed solid was filtered, and the wet compound was washed with water. The wet compound was dissolved in 3525 ml acetic acid by heating to 70 to 80 C., then carbon was added and the mixture was stirred briefly at the same temperature, and the carbon was removed by filtration and washed with 15 ml of acetic acid. The filtrate was allowed to cool to about 20 C. for solid formation. The solidd was filtered, washed three times with 600 ml of water, and then dried to yield 148.5 g of the title compound.

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; Venkataraman, Sundaram; Rao, Uppala Venkata Bhaskara; Muvva, Venkateswarlu; Chitta, Vijayawardhan; US2006/89502; (2006); 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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H4ClNO2

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 5-Chloro-1-methylindoline-2,3-dione

General procedure: A solution of N-methylisatin (161 mg, 1.0 mmol), indole (129 mg, 1.1 mmol), and K2CO3 (69 mg, 0.5 mmol) in aqueous DMF (H2O/DMF, 2:1, 3.0 mL) was heated to 50 oC for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 1a was obtained as a white solid, 170 mg (61%).1,2 Other compounds were synthesized similarly, and compounds 1a1,2 and 1l3,7 are known compounds. Compound1a?1,4 was prepared according to the reported method.16 The spectroscopic data of unknown compounds 1b-d are as follows.

The synthetic route of 60434-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Note; Seo, Da Young; Roh, Hwa Jung; Min, Beom Kyu; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 12; (2017); p. 1519 – 1522;,
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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. 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Chloro-7-methylindoline-2,3-dione

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 14389-06-1.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
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