Tag: M.W=100-200

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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6ClNO2

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. .1.54 2-((2-(2-(Butan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (2C) White powder, mp 135-142 C, 87% yield; 1H NMR (400 MHz, CDCl3): delta 1.08-1.12 (t, 3H, CH3), 2.20 (s, 3H, CH3), 2.27-2.31 (q, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.76 (bs, 2H, Ar), 7.86-7.87 (m, 2H, Ar).

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; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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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 39603-24-2 as follows. Formula: C10H9NO2

General procedure: A solution of isatin (1 mmol), barbituric acid (1 mmol), 3-amino-5-methyl isoxazole (1 mmol), and p-TsOH (0.2 mmol) in water (10 mL) was stirred for 24 h at 70 C in oil bath. After completion of the reaction, which was followed by TLC (n-hexane/EtOAc), the warm reaction mixture was filtered. The residue was washed with water and then recrystallized from ethanol to give the pure product.

According to the analysis of related databases, 39603-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rahmati, Abbas; Khalesi, Zahra; Tetrahedron; vol. 68; 40; (2012); p. 8472 – 8479;,
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Synthetic Route of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

NONOate salt N001 (0.270 g, 1.58 mmol) suspended in acetonitrile (3.0 mL) was treated with a solution of N-(chloromethyl)phthalimide (0.280 g, 1.43 mmol) in acetonitrile (3.0 mL) and then sodium iodide (0.215 g, 1.43 mmol) was added. The resulting mixture was stirred at 25 C overnight. N,N-dimethylformamide (1.0 mL) was added to the reaction mixture which was then heated to 60 C for 1 hour. The acetonitrile was removed under reduced pressure. The residue was suspended in ethyl acetate and then washed with a 0.2 N solution of sodium thiosulfate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was subjected to prep-chromatography using ethyl acetate in hexane to provide a tan oily solid (14 mg, 3.0% yield). 1H NMR (400 MHz, CDC13) delta 7.92-7.87 (m, 2H), 7.78-7.73 (m, 2H), 5.67 (s, 2H), 2.97 (s, 1H), 2.19 (s, 2H), 1.59 (s, 6H). LC tr=2.65 minutes (C- 18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C). ES(pos)MS m/z 331 (M+Na calcd for C13Hi6N405 requires 331).

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

Reference:
Patent; EUCLISES PHARMACEUTICALS, INC.; MARTINEZ, Eduardo, J.; TALLEY, John, J.; JEROME, Kevin, D.; BOEHM, Terri, L.; WO2014/12074; (2014); A2;,
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These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-2-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. Formula: C9H9NO

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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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. 222036-66-0, name is 5-Aminoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 222036-66-0

A mixture of 5-aminoisoindolin-1-one (50mg, 0.34mmol), the compound id (172mg, 0.5 lmmol), p-toluenesulfonic acid (96mg, 0.5 lmmol), and n-BuOH (5mL) was stirred at 70°C for3 hours. The mixture was cooled and concentrated under reduced pressure; the residue was20 purified by Pre-TLC to afford the compound 8 as yellow solid (25mg, 16percent). MS: 45 1(M+H).H-NMR (DMSO-d6, 400MHz): oe 11.18 (s, 1H), 9.98 (s, 1H), 8.92 (s, 1H), 8.40 (s, 1H), 8.02 (s, 1H), 7.57-7.79 (m, 4H), 7.30 (t, 1H), 4.30 (s, 2H), 3.00 (s, 3H), 2.90 (s, 3H).

The synthetic route of 222036-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; ZHOU, Wenlai; LI, Runze; GAO, Panliang; WU, Xinping; BAI, Jinlong; YANG, Guiqun; WANG, Yanping; KANG, Di; (84 pag.)WO2018/19252; (2018); A1;,
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Electric Literature of 480-91-1, 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. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of sodium hydride (450.6 mg, 11.26 mmol), freshly washed with hexane and suspended indry THF, was added a solution of isoindolin-1-one (1.00 g, 7.51 mmol) in tetrahydrofuran (25 mL) at 0 Cunder a nitrogen atmosphere. The reaction mixture was stirred (30 min) before tert-butyl bromoacetate(1.664 mL, 11.26 mmol) was added slowly. The reaction mixture was stirred (16 h) at room temperature.The reaction mixture was quenched with methanol (5 mL). The solvent was removed under vacuum andthe resulting crude residue submitted to column chromatography (hexane/ethyl acetate, 4:1) to givepure tert-butyl 2-(1-oxoisoindolin-2-yl)acetate 1 as an off-white solid (1.802 g, 97%); mp = 62-64 C; Rf =0.33 (ethyl acetate/hexanes, 2:1); FT-IR (neat): 2972, 2932, 1738, 1687 cm -1; 1H NMR (400 MHz, CDCl3):delta 7.86 (d, J = 7.6 Hz, 1H), 7.54-7.52 (m, 1H), 7.47-7.43 (m, 2H), 4.51 (s, 2H), 4.29 (s, 2H), 1.46 (s, 9H). 13CNMR (100 MHz, CDCl3): delta 168.8, 168.1, 141.6, 131.9, 131.6, 127.9, 123.9, 122.7, 82.2, 50.5, 44.5, 28.0.ppm; LRMS calcd for C14H17NO3 (M+H) 248, found 248.

The chemical industry reduces the impact on the environment during synthesis Isoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Synlett; vol. 28; 14; (2017); p. 1729 – 1732;,
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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. 324-03-8, name is 6-Fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Fluoroindoline-2,3-dione

Step 1 : 7-fluoroquinoline-2,4-dicarboxylic acid To a mixture of 5.0 g (30.3 mmol) 6-fluoro-1 H-indole-2,3-dione in 75 mL of 33% aq. potassium hydroxide solution was added 4.67 g (53.0 mmol) pyruvic acid and this mixture was heated at 40 C for 18 hours. After cooling to room temperature 10% aq. sulfuric acid was added (pH about 1 ). The formed solid was isolated by filtration and dried in vacuum. The solid was the desired 7-fluoroquinoline-2,4-dicarboxylic acid, which was used without further purification. Yield: 6.02 g (85%) 1H-NMR (300 MHz, DMSO d6) delta (ppm) = 7.78 (ddd, 1 H), 7.99 (dd, 1 H), 8.42 (s, 1 H), 8.89 (dd, 1 H).

The synthetic route of 324-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (248 pag.)WO2016/12481; (2016); A1;,
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Reference of 59-48-3, 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 59-48-3 as follows.

To 5 L 4-neck flask (equipped with a mechanical stirrer, condenser and N2 inlet) was charged with 2 L water and 50% sodium hydroxide (NAOH) (2.52 mol, 201.6 g, 2.25 equiv) followed by oxindol (1.12 mol, 150 g, 1 equiv) and the reaction mixture was heated TO-40 C. Dimethylsulfate (1.68 mol, 211.7 g (159 mL), 1.5 equiv) was added slowly via syringe. The addition was slightly exothermic with temperature rising to 53 C. When addition was complete, the reaction mixture was heated to- 100 C and held for 15 minutes (min). The reaction mixture was cooled TO-600 C, and a second portion of dimethylsulfate (0.476 mol, 60 g (45 mL), 0.425 equiv) was added. The reaction mixture was heated TO ~ 100 C and held 15 min. TLC (heptane/ethyl acetate (EtOAc), 1: 1) show methylation was essentially complete. The reaction mixture was cooled TO-50 C and the pH adjusted to-7 with concentrated HCI. The reaction mixture was seeded, cooled to room temperature and allowed to stand overnight. The solids were collected, wash with water (4X) and dried overnight in a vacuum over AT-40 C to give 110.7 g (67%) of 1-methyl-1, 3-dihydroindol-2-one as a pink solid, mp 84-86 C.

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2004/37820; (2004); A1;,
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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 100510-65-4 as follows. Safety of 6-Amino-3,3-dimethylindolin-2-one

570 mg (2.20 mmol) of ethyl 3-ethoxy-2-[(ethoxycarbonyl)carbamoyl]acrylate and 388 mg (2.20 mmol) of 6-amino-3,3-dimethyl-1,3-dihydro-2H-indol-2-one [for preparation see: US 2006/258689, page 35] were initially charged in 14 ml of ethanol and heated to reflux for 2 h. Subsequently, at RT, 247 mg (2.20 mmol) of potassium tert-butoxide were added and the mixture was stirred at RT for 1 h and at 60 C. for 1 h. For workup, the reaction mixture was admixed with water, acidified with 1N hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated. The residue was subjected to extractive stirring in MTBE/ ethyl acetate, and the solid formed was filtered off, washed with ethyl acetate and then dried at 50 C. under reduced pressure. This gave 630 mg (79% of theory) of the title compound. LC-MS (Method 1): Rt=0.65 min; MS (ESIpos): m/z=344 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.22 (t, 3H), 1.28 (s, 6H), 4.16 (q, 2H), 6.96-7.01 (m, 1H), 7.04-7.09 (m, 1H), 7.42 (d, 1H), 8.27 (s, 1H), 10.58 (s, 1H), 11.65 (s, 1H).

According to the analysis of related databases, 100510-65-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
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Reference of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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.

Potassium phthalimide (49 gm) was added to a solution of (Z)- 1 -phenyl- 1- diethylamino carbonyl-2-chloromethyl cyclopropane obtained in step-(c) at 20-30C. The reaction mixture was heated to 80-85C, stirred for 2-3 hrs at the same temperature and then cooled to 20-30C. The resulting reaction mixture containing (Z)- 1 -phenyl- 1- diethylaminocarbonyl-2-phthalimidomethyl cyclopropane was utilized in the next step without isolating the compound from the reaction mixture.

Statistics shows that Potassium 1,3-dioxoisoindolin-2-ide is playing an increasingly important role. we look forward to future research findings about 1074-82-4.

Reference:
Patent; MSN LABORATORIES LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; SATYANARAYANA, Revu; WO2012/46247; (2012); A2;,
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