Tag: M.W=100-200

Related Products of 611-09-6, A common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10mol %), CH2Cl2 (10 mL) was added to 50 mL flask and stirred at room temperature until the thecompletion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH2Cl2 (5mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which wasrecrystallized from ethanol to produce pure crystalline products. The products were identified byelemental analysis, MS, 1H NMR, 13C NMR, and IR spectra.

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; Yu, Jiangxia; Shen, Tianhua; Lin, Yan; Zhou, Yongbing; Song, Qingbao; Synthetic Communications; vol. 44; 14; (2014); p. 2029 – 2036;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Methylindoline

General procedure: Diphenyliodonium triflate (2a, 0.1 g, 0.23 mmol, 1.1 equiv) was charged in a vial and sealed with a septum. After adding TFE (3mL), indoline (1a, 0.024 mL, 0.21 mmol) was added dropwise slowly to the solution, which was then heated to 70 C for 14 h.After the solution was cooled to r.t., the mixture was diluted with H2O and sat. NaHCO3. The aqueous phase was extracted several times with CH2Cl2. The organic phase is washed with H2O, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel, eluting with cyclohexane-CH2Cl2 (2:1, v/v) giving 34 mg(83%) of 3a as a colorless solid.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Riedmueller, Stefan; Nachtsheim, Boris J.; Synlett; vol. 26; 5; (2015); p. 651 – 655;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, These common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, 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.

To a solution of 5-nitroindoline (1 g, 6.09 mmol) in dry DMF (20 ml), K2CO3 (1.094 g, 7.92 mmol) and benzyl 2-bromoacetate (1.242 ml, 7.92 mmol) were added, and the resulting suspension was heated at 65 C. for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and the solvent was removed. The residue was purified by flash chromatography on silica gel column (DCM:petroleum ether=60:40) affording benzyl 2-(5-nitroindolin-1-yl)acetate (0.782 g, 2.504 mmol, 41% yield). MS/ESI+ 312.9 [MH]+.

Statistics shows that 5-Nitroindoline is playing an increasingly important role. we look forward to future research findings about 32692-19-6.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 102359-00-2 as follows. SDS of cas: 102359-00-2

EXAMPLE 15 To a solution of 0.88 g of 5-carboxyoxindol in 10 ml of DMF was added under ice-cooling 0.82 ml of triethylamine, and 0.77 ml of isobutyl chloroformate was added thereto subsequently. The mixture was stirred at the same temperature for 1 hour. Then, 1.1 g of 1-benzylpiperazine was added thereto, and the mixture was stirred at room temperature overnight. After the reaction was completed, DMF was removed under reduced pressure, and to the residue was added an aqueous sodium hydrogencarbonate solution and extracted with chloroform. After washing with water and drying over magnesium sulfate, chloroform was distilled off under reduced pressure. The resultant residue was purified by silica-gel column chromatography (eluent: methylene chloride_methanol=50:1) and recrystallized from isopropyl alcohol to give 0.7 g of 5-(4-benzyl-1-piperazinylcarbonyl)oxindol. m.p.: 151-153 C.

According to the analysis of related databases, 102359-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 150544-04-0, 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. 150544-04-0, name is 6-Aminoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,4-dichloro-5-trifluoromethylpyrimidine (3.51 g; 16.2 mmol) in THF (100 mL) was added a solution of ZnCl2 (1M in ether; 16.2 mL). After 15 minutes 6-aminooxindole (2 g; 13.5 mmol) was added in small portions, followed by the dropwise addition of Et3N (1.63 g; 16.2 mmol) in 10 mL of THF. The reaction was then stirred at RT overnight. Following removal of the solvent under reduced pressure, the crude reaction was triturated from methanol and the product filtered off as a yellow solid 2.2 g (50percent yield). 1H NMR (DMSO-d6, 400 MHz) delta 3.40 (s, 2H), 7.13 (d, J=8.3 Hz, 2H), 7.20 (d, J=7.9 Hz; 1H), 7.27 (br s, 1H), 8.75 (s, 1H), 10.41 (s, 1H), 10.62 (s, 1H); HPLC ret. time: 5.933 min. LRMS (M+) 329.1, 331.0.

The chemical industry reduces the impact on the environment during synthesis 6-Aminoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US2005/256125; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3485-84-5, 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. 3485-84-5 name is N-Vinylphthalimide, 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.

b) Racemic-cis-2-(2-phenyl-cyclopropyl)-isoindole-1,3-dione 2.00 g (7.29 mmol) benzaldehyde tosyl hydrazone are placed in 40 ml of tetrahydrofuran and cooled to -70 C. 7.29 ml (7.29 mmol) LiHMDS lithium bis(trimethylsilyl)amide (1 M solution in tetrahydrofuran) are added, then the mixture is stirred for 0.25 hours at -78 C. The reaction mixture is slowly heated to ambient temperature, then concentrated by evaporation. The residue is dissolved in 50 ml dioxane, combined with 0.166 g (1 mmol) benzyltriethylammonium chloride and 0.032 g rhodium acetate-dimer, and 6.31 g (36.45 mmol) 2-vinyl-isoindole-1,3-dione added. The reaction mixture is stirred for 80 hours, then extracted with water and dichloromethane. The organic phase is dried and evaporated to dryness. The residue is purified by chromatography. Yield: 0.650 g (34% of theoretical)

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

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/116370; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 675109-45-2

To a solution of 6-amino-2,3-dihydroisoindol-1-one (1.78 g, 12 mmol) in DMF/H2O (2:1, 75 ml) was added K2CO3 (3.32 g, 24 mmol, 2 eq.) and di-tert-butyl dicarbonate (5.67 g, 26 mmol, 2.2 eq.). The reaction was stirred at room temperature overnight. The reaction was partitioned between ethyl acetate and water, and the organic layer was washed with saturated NaCl (aq), dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and the resulting solid was filtered off to afford title compound (2.04 g, 68%). 1H NMR (360 MHz, d6 DMSO) ? 8.48 (1H, s), 7.83 (1H, d, J=1.2 Hz), 7.6 (1H, dd, J=8.2, 1.9 Hz), 7.43 (1H, d, J=8.2 Hz), 4.28 (2H, s), 1.49 (9H, s).

According to the analysis of related databases, 675109-45-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boase, Amanda Louise; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; US2004/58970; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 2058-74-4,Some common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, molecular formula is C9H7NO2, 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 1 (3 mmol), 0.198 g malononitrile (3 mmol),0.420 g dimedone (3 mmol), and 0.025 g sodium acetate(0.3 mmol) were grinded with the pestle in mortar atambient temperature for 15 min. The resulting mixture wasair dried. Crude solid was then put on filter, rinsed withwater (2 9 2 cm3), and dried with water pump.

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

Reference:
Article; Elinson, Michail N.; Ryzhkov, Fedor V.; Zaimovskaya, Tatiana A.; Egorov, Mikhail P.; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 755 – 760;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 7699-18-5 as follows. Computed Properties of C9H9NO2

General procedure: In 50 mL round flask, 4-(4-(hydrazinecarbonyl)-5-amino-1H-pyrazol-1-yl)benzenesulfonamide 15 (10 mmol, 0.3 g) was dissolvedin ethanol (20 mL) followed by the addition of the appropriate isatin derivative (10 mmol). Reflux was performed after the addition of a catalytic amount of acetic acid (0.5 mL) for 1 h. The formed precipitate, in case of 16a-e, was filtered, washed with hot ethanol and recrystallized from DMF / EtOH to give the targeted compounds 16a-e. Concerning compound 16f, the precipitate formed after cooling was filtered and recrystallized from DMF /EtOH. 4.1.7.4 4-(5-Amino-4-(2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazine-1-carbonyl)-1H-pyrazol-1-yl)benzenesulfonamide (16d) Orange powder, 85% yield; mp > 300 C. IR (KBr) numax/cm-1 3414-3190 (NH2, NH), 1722-1690 (C=O), 1512 (C=N), 1322, 1156 (SO2). 1H NMR (DMSO-d6, 400 MHz) delta 3.80 (s, 3H, OCH3), 6.82 (d, 1H, J = 8.4 Hz, H-7 isatin), 6.96 (d, 2H, J = 10.2 Hz, Ar-H), 7.07 (s, 2H, NH2, D2O exchangeable), 7.49 (s, 2H, SO2NH2, D2O exchangeable), 7.83 (d, 2H, J = 8.4 Hz, Ar-H), 8.00 (d, 2H, J = 8.4 Hz, Ar-H), 8.61 (s, 1H, H-3 of pyrazole), 10.61, 11.07 (s, 1H, NH isatin, D2O exchangeable), 11.38, 13.02 (2s, 1H, NH hydrazone, D2O exchangeable). 13C NMR (DMSO-d6, 100 MHz) delta 56.41, 95.92, 111.50, 112.13, 116.20, 118.52, 121.22, 123.18, 123.97, 127.51, 137.77, 140.83, 142.96, 143.31, 152.46, 155.11, 155.83, 165.69, 166.47. MS m/z [%] 455 [M+, 9.06], 223 [100]. Anal. Calcd for C19H17N7O5S (455.45): C, 50.11; H, 3.76; N, 21.53; S, 7.04. Found: C, 50.27; H, 3.83; N, 21.75; S, 7.13.

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ibrahim, Hany S.; Abou-Seri, Sahar M.; Tanc, Muhammet; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 583 – 593;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C10H9NO2

The propyne acid 4 – nitrophenyl-unitz (57.3 mg 0.3 mmol), was used. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-like (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 0.3 mmol 45 mul -) and methylene chloride unitunitunito shown in the formula IV are placed in 3 ml a 25 ml unitunito-two-4h port bottle, reacted 30 C, and concentrated, under inert atmosphere protection, unitunitunitaceous conditions, and petroleum ether: petroleum ether: The ethyl acetate ratio 10:1 mixed solvent is eluted, eluent fractions, and the detected eluent fractions of all the products are collected, the solvent is evaporated and 25 mg the solvent is evaporated to obtain the unitz , which is a unitless 75%.

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem