Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, 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 3676-85-5, Computed Properties of C8H6N2O2

2.0 parts of a formyl derivative represented by the following formula (2) and 2.0 parts of 4-aminophthalimide represented by the following formula (3) are added to 20 parts of acetic acid and stirred at 40 C. for 6 hours The solution thus obtained was cooled to room temperature, poured into 50 parts of water, stirred for 30 minutes, and the precipitated solid was collected by filtration, washed with water and dried to obtain No. 1 of the above specific example. 1.5 parts of a methine compound (lambda max: 435 nm) represented by 1 was obtained.

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Reference:
Patent; NIPPON KAYAKU COMPANY LIMITED; TAKAHASHI, MASAYUKI; (14 pag.)JP2015/189767; (2015); A;,
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3676-85-5, name is 5-Aminoisoindoline-1,3-dione, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H6N2O2

After 80 parts of water was added to 4- (manufactured by Tokyo Kasei Kogyo Co., Ltd.) amino phthalimide 16.2 parts, 0.4 parts of sodium hydroxide was added and dissolved.Under ice cooling, 35% aqueous sodium nitrite solution 19.7 parts was added, followed by 35% hydrochloric acid 26.2 parts was stirred for 2 hours and dissolved by adding little by little to obtain a suspension containing a diazonium salt.[0068]Then, 23.9 parts of 6-amino-4-hydroxy-2-naphthalenesulfonic acid was suspended in 100 parts of water, with sodium hydroxide, the pH was adjusted to 9.0.Here it was added dropwise by a pump over a period of suspension 15 minutes including the diazonium salt.After completion of the addition, to obtain a suspension of yellow by stirring for an additional 30 minutes.After stirring for 1 hour the suspension was stirred for 1 hour.The obtained filtered red solid was dried under reduced pressure at 60 C., to obtain a compound represented by formula (I-1) 40.5 parts.Measurement of the maximum absorption wavelength of this compound, lambdamax was 545nm.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company Limited; Ashida, Toru; (22 pag.)JP5831135; (2015); B2;,
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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 129487-92-9 as follows. name: tert-Butyl 5-aminoindoline-1-carboxylate

The 1-tert-butoxy-carbonyl-5-amino indoline (3g, 14mmol) dissolved in water (3 ml) in, cooling to-5-0 C degrees, dropping sodium nitrite (1.16g, 16 . 8mmol) of water (3 ml) solution, 0 C stirring for 30 minutes, a diazo reaction liquid obtained, the spare; sodium acetate (2.64g, 32 . 2mmol) dissolved in water (3 ml) in, by adding 2-chloro acetyl ethyl acetate (2.3g, 14 . 0mmol) second grade fat of the acetic acid (5 ml) solution, cooled to 0 C, spare the dropping of a diazo reaction solution, 0 C reaction 1 hour. Adding water to the reaction solution (50 ml), ethyl acetate (50 ml ¡Á 3) extraction, combined organic phase, the organic phase with water (50 ml ¡Á 2) washing, dry anhydrous sodium sulfate, concentrated, the title compound ethyl 2-chloro-2-(2-(indolin-5-yl)hydrazono)acetate (25B), yellow solid (1.2g, yield 32%).

According to the analysis of related databases, 129487-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO LTD; WEI, YONGGANG; QIU, GUANPENG; LEI, BAILIN; LU, YONGHUA; (120 pag.)CN104395312; (2016); B;,
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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 61-70-1 as follows. SDS of cas: 61-70-1

Add sodium hydride (60%, 1.4 g, 35.4 mmol) portionwise to the solution of 1-methylindolin-2-one (2.6 g, 17.7 mmol) in DMF (10 mL) at 0 C., stir for 30 min. Then add 1,2-dibromoethane (3.31 g, 17.7 mmol) to the mixture, stir the resulting mixture at room temperature overnight. Pour the reaction mixture to ice water, extract with ethyl acetate (100 mL*2), and wash the combined organic layers with brine (50 mL), dry over anhydrous sodium sulfate. Concentrate under reduced pressure, purify the residue by chromatography (silica gel, EtOAc_PE=1:3) to provide the title compound (1.5 g, 50.0%). MS: (M+1): 174.

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhang, Deyi; Zhang, Ruihao; Zhong, Boyu; Shih, Chuan; US2015/197511; (2015); 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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of Indolin-2-one

5-Amino-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one 2-Oxindole (6.5 g) was dissolved in 25 mL of concentrated sulfuric acid and the mixture maintained at -10-15 C. while 2.1 mL of fuming nitric acid was added dropwise. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hour and poured into ice-water. The precipitate was collected by filtration, washed with water and crystallized from 50% acetic acid. The final crystalline product was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
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Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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: 118289-55-7

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 118289-55-7, its application will become more common.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 7-Fluoro-1-methylindoline-2,3-dione

General procedure: To a mixture of 2-hydroxy-1,4-naphthoquinone (1 mmol), isatin (1 mmol) and CH3COOH10 mL, 5-aminotetrazole (1 mmol) was added. The mixture was stirred at reflux for an appropriatetime (Table 2). After completion of the reaction (TLC), the reaction mixture was cooled to roomtemperature and the solvent was evaporated under reduced pressure. Then, the crude product waswashed sequentially with 20 mL saturated NaHCO3 and 20 mL brine, purified by silica gel columnchromatography using petroleum ether: ethyl acetate (v:v = 1:1) as eluent to afford the pure product 4(the copies of all spectral data see Supplementary Materials).

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Liqiang; Liu, Yunxia; Li, Yazhen; Molecules; vol. 23; 9; (2018);,
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Synthetic Route of 919103-45-0,Some common heterocyclic compound, 919103-45-0, name is 6-Iodoindolin-2-one, molecular formula is C8H6INO, 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.

A nitrogen purged vessel is loaded with starting material 6-lodoindolinone (1 05kg,405mo1, 1,0 eq), catalyst 4-dimethylaminopyridine (DMAP) (2,52 kg) under argoncounter flow. Then triethylamine (145 kg, 3,5 eq) and solvent 2-methyltetrahydrofuran(605 kg) are charged to the vessel and the resulting solution is cooled to -15 00 to-S00 (preferentially -10C). Benzoylchloride (176,6 kg, 3,1 eq) is added to this mixture atan internal temperature of 100C to 50C within at least 30mm.The addition funnel is then flushed with 2-methyltetrahydrofuran (22 kg) and the reaction mixture is stirred for an additional hour at an internal temperature of 10 to 30C. If the content of starting material 6-iodoindolinone is greater than 2,5 area%(H PLC), another portion of benzoylchloride (5,7 kg) is added to complete the reaction. If the content of starting material 6-iodoindolinone is smaller than 2,5 area% (H PLC), lithium hydroxide (59,4 kg, 6,0 eq) is added in 5 differently sized portions (1st: 18,0 kg, 2?: 6,0 kg, 3: 6,0 kg, 41h: 15,0 kg, 5th: 14,4 kg) in a temperature controlled manner:After the two first portions, the mixture is stirred for 1 hour. After portion 3 and 4, the mixture is stirred for 30mm. After the last portion, the mixture is stirred for two hours. The reaction mixture (suspension) is then stirred for at least 12 hours at an internal temperature of 20 to 30 C. If the content of the non isolated intermediate of formula (V) is smaller than 0,5 area% (H PLC), water (525 L) is added and the mixture is heatedto an internal temperature of 60 to 7000 under stirring. Then the stirrer is switched off, the mixture is settled down and the phases are separated at an internal temperature of 60 to 70C. To the upper organic layer, water (525 L) is added and a second phase separation is carried out at an internal temperature of 60 to 70C. (Optionally, the mixture might be left stand at room temperature for up to 24 hours.) Then a partial solvent switch to tetrahydrofuran is carried out: Solvent is distilled off three times at a jacket temperature of 70C down to a residual volume of 390L followed by addition of tetrahydrofuran (1st: 233 kg, 2nd. 233 kg, 3rd. 117 kg). For crystallization, firstly, methanol (83 kg) is added.Optionally, the mixture might be left stand at room temperature for up to 24 hours. Secondly, water (112 L) is added at an internal temperature of 60 to 70C, followed by addition of conc. hydrochloric acid (156,2 kg). The addition funnel is flushed with water (20 L). The resulting suspension is cooled to 20 to 30C within at least 70mm (optionally, the mixture might be left stand at room temperature for up to 72 hours) and then to an internal temperature of minus 5 to 5 C within at least 30mm. The suspension is then centrifuged and the solid is washed with water (368 L) followed by methanol (112 kg) and dried at a jacket temperature of 50C until <= 1% of residual solvent is reached. The enol product of formula (IV) is obtained as solid in 84,6% yield. The synthetic route of 919103-45-0 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MAIER, Gerd-Michael; BAUM, Anke; BETZEMEIER, Bodo; HENRY, Manuel; HERTER, Rolf; REISER, Ulrich; SINI, Patrizia; WEBER, Dirk; WERTHMANN, Ulrike; ZAHN, Stephan Karl; WO2014/9318; (2014); A1;,
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Electric Literature of 496-12-8, 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 496-12-8 as follows.

(1) Triethylamine (3.48 mL, 25.0 mmol) was added to a solution of isoindoline (4.98 g, 25.0 mmol) in chloroform (100 mL) at room temperature and the mixture was cooled in ice. Trichloroacetic acid chloride (2.79 mL, 25.0 mmol) was added dropwise thereto and the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1) to afford 2,2,2-trichloro-1-(1,3-dihydro-2H-isoindol-2-yl)ethanone as a purple powder (6.59 g).

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; BUSUJIMA, Tsuyoshi; OI, Takahiro; TANAKA, Hiroaki; SHIRASAKI, Yoshihisa; IWAKIRI, Kanako; SATO, Nagaaki; TOKITA, Shigeru; EP2687507; (2014); A1;,
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Electric Literature of 16800-68-3, 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.

General procedure: A 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t. (2S,3?S)-tert-Butyl (1-Acetyl-1?-methyl-2?,3-dioxo-[2,3?-biindolin]-3?-yl)carbamate (3a)Yield: 165 mg (86%); colorless solid; mp 162-163 C; [alpha]D27 -21.4 (c0.5, CHCl3).HPLC: CHIRALPAK IB, n-heptane/EtOH (7:3), 1.0 mL/min, tR (major) =8.5 min, tR (minor) = 11.4 min, lambda = 230 nm; >20:1 dr; 99% ee.IR (ATR): 3307, 2962, 2641, 2322, 2083, 1919, 1902, 1811, 1771, 1709,1602, 1581, 1334, 755, 654 cm-1.1H NMR (400 MHz, CDCl3): delta = 7.55 (m, 2 H, NH, ArH), 7.44 (d, J = 8.0Hz, 1 H, ArH), 7.25 (d, J = 8.0 Hz, 1 H, ArH ), 7.00 (td, J = 8.0, 4.0 Hz, 2 H,ArH), 6.90 (d, J = 8.0 Hz, 1 H, ArH), 6.59 (d, J = 4.0 Hz, 1 H, ArH), 6.51 (t,J = 8.0 Hz, 1 H, ArH), 5.12 (s, 1 H, CH), 3.17 (s, 3 H, NMe), 2.53 (s, 3 H,COCH3), 1.19 [s, 9 H, C(CH3)3].13C NMR (101 MHz, CDCl3): delta = 192.4, 172.8, 171.9, 153.6, 152.5,143.7, 136.4, 129.3, 126.5, 125.5, 124.7, 124.2, 123.6, 121.6, 117.3,108.0, 79.9, 69.4, 64.4, 28.0 (3 C), 26.2, 24.2.MS (ESI): m/z = 458.1 [M + Na]+.HRMS (ESI): m/z [M + Na]+ calcd for C24H25N3O5Na: 458.1686; found:458.1687.

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

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
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