Indolines-derivatives

Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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. COA of Formula: C14H13NO3

Example 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22 g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104618-32-8, its application will become more common.

Reference:
Patent; Smithkline Beecham plc; US5827871; (1998); A;,
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Synthetic Route of 22190-33-6, 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. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows.

Step 2. fert-Butyl-5-bromoindoline-l-carboxylate (BI12): To a stirred solution of 5- bromo-indoline (3.0 g , 15mmol) in acetonitrile (100 ml), was added DMAP (0.185 g , 1.522 mmol) and di-ieri-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at RT for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2X). The combined ether layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

The chemical industry reduces the impact on the environment during synthesis 5-Bromoindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Oxoindoline-5-carboxylic Acid

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

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; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
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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. 550-44-7, name is 2-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Methylisoindoline-1,3-dione

Add a nitrating agent to N-methylphthalimide at -5 C, and react at 40 C for 4h, then extract with an extraction solvent dry,N-methyl-4-nitrophthalimide is formed.The extraction solvent is ethyl acetate and dichloromethane, and the weight ratio is 1: 0.6. The weight ratio of the extraction solvent and N-methylphthalimide is 1: 1.

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 550-44-7.

Reference:
Patent; Shandong Juancheng Fangyuan Bearing Chemical Co., Ltd.; Li Zhi; Zhang Hongyuan; Zhang Heji; (13 pag.)CN110437131; (2019); A;,
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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 41910-64-9 as follows. Recommanded Product: 41910-64-9

General procedure: To the appropriate cyclic amine (20 mmol) in hexane (15 mL) amyl nitrite (60 mmol, 7 g, 8 mL) was added in one portion. The resulting mixture was stirred for 30 min at room temperature. The precipitated solid was collected by filtration, washed with hexane, dried and used for preparation of corresponding N-aminoindolines 3a-d and N-amino-1,2,3,4-tertahydroquinolines 7a,b without purification.

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; S?czewski, Franciszek; Wasilewska, Aleksandra; Hudson, Alan L.; Ferdousi, Mehnaz; Rybczy?ska, Apolonia; Boblewski, Konrad; Lehmann, Artur; Acta poloniae pharmaceutica; vol. 72; 2; (2015); p. 277 – 287;,
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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. 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H4ClNO4S

To a slurry of 2,3-dioxomdoline-5-sulfonyl chloride (Lee, D. et al. J. Med. Chem. 2001, 44, 2015) (7,07 g, 28.8 mmol) m CH2Cl2 (288 mL) at rt was added neopentyl alcohol (7.61 g, 86.3 mmol) then pyridine (11.6 mL, 143 mmol). The reaction was stirred at rt for 22 hours, becoming a clear, oiange solution. The reaction was diluted with ILO (300 mL) and extracted with EtOAc (2 chi 600 mL). The combined organic extracts were washed with 0.1 M aqueous HCl (3 * 300 mL), saturated aqueous NaHCO3 (300 mL), and saturated aqueous NaCl (300 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound as a yellow solid (6.40 g, 92%). 1H NMR (400 MHz, CDClj): consistent; MS (ES ) m’z 315.1 (,VHH2O)

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 132898-96-5.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
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These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-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. COA of Formula: C10H11NO

EXAMPLE 10 5-Bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one: 3,3-Dimethyl-1,3-dihydro-2H-indol-2-one (1.12 g, 6.95 mmol) was dissolved in chloroform and stirred at room temperature under nitrogen. Bromine (1.12 g) was added and the mixture was heated under reflux until HBr evolution ceased and the bromine colour was discharged from the solution. The solution was washed with sodium metabisulphite solution and sodium hydrogen carbonate solution, dried (MgSO4), filtered and concentrated to dry under reduced pressure to give 5-bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a yellow solid. 1 H NMR (CDCl3) d1.39 (6H s), 6.8 (1H d), 7.3 (2H m), 7.9 (1H broad)

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

Reference:
Patent; Eli Lilly and Company Limited; US5773448; (1998); A;,
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Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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. Recommanded Product: 6-Chloroisatin

D. 6-Chloro-2-oxindole Reaction of 36.2 g of 6-chloroisatin with hydrazine hydrate followed by sodium ethoxide in ethanol, substantially according to C above, afforded 14.2 g of 6-chloro-2-oxindole, m.p. 196-198 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6341-92-0, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4556672; (1985); A;; ; Patent; Pfizer Inc.; US4569942; (1986); A;; ; Patent; Pfizer Inc.; US4690943; (1987); A;,
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Adding a certain compound to certain chemical reactions, such as: 1127-59-9, name is 7-Methylindoline-2,3-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 1127-59-9, Quality Control of 7-Methylindoline-2,3-dione

General procedure: Isatin 1 (3 mmol), malononitrile (0.2 g, 3 mmol,), bicyclic CH-acid 2 (3 mmol) and sodium acetate (0.025 g, 0.3 mmol) in ‘solvent-free’ manner or with additive (‘on-solvent’ manner) were grinded with a pestle and mortar at ambient temperature for 15 minutes. After the reaction was finished, the mixture was air-dried. Then the crude solid was put on filter, rinsed with water (2 mL) and EtOH (2 mL), and then dried with a water pump to isolate the spiro-oxindole 3.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elinson, Michail N.; Vereshchagin, Anatoly N.; Ryzhkov, Fedor V.; Anisina, Yuliya E.; Arkivoc; vol. 2018; 4; (2018);,
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Related Products of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 25c (2.00 g, 6.94 mmol) and 7a (2.00 g, 10.6 mmol) in THF (70 mL) was added NH4OAc (5.40 g, 70.0 mmol) in MeOH (50 mL). The reaction mixture was stirred at room temperature for 3.5 h. A saturated aqueous solution of NaHCO3 was added to the reaction mixture and extracted with EtOAc three times. The combined organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 60-80percent EtOAc/n-Hexane, on silica gel eluting with 5percent MeOH/CHCl3, and on silica gel eluting with 65percent EtOAc/CHCl3 to afford 2-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione as a pale yellow powder (1.90 g, 60percent): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.8 Hz, 3 H), 5.08 (s, 2 H), 6.74 (br s, 1 H), 7.71 – 7.94 (m, 6 H), 8.16 (d, J = 8.5 Hz, 1 H), 9.03 (s, 1 H); MS (ESI) m/z 458 [M+H]+, 30percent, 480 [M+Na]+, 100percent, 456 [M-H]-, 100percent. To a suspension of 2-{[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methyl}-1H-isoindole-1,3(2H)-dione (1.88 g, 4.11 mmol) in EtOH (45 mL) was added hydrazine monohydrate (2.12 g, 42.3 mmol). The reaction mixture was stirred at room temperature for 1 day. MeOH, CHCl3, and NH-silica gel were added to the reaction mixture and concentrated. The residue was purified by column chromatography on NH-silica gel eluting with 5percent MeOH/CHCl3 and on silica gel eluting with 10percent MeOH/CHCl3 to 28percent aqueous ammonia/MeOH/CHCl3 (1/10/100) to afford 1-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methanamine as a pale yellow amorphous (761 mg, 57percent): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 1.1 Hz, 3 H), 4.12 (s, 2 H), 6.72 (d, J = 1.1 Hz, 1 H), 7.87 (dd, J = 8.5, 1.7 Hz, 1 H), 8.17 (dd, J = 8.5, 0.5 Hz, 1 H), 8.45 (br s, 1 H), 9.03 (s, 1 H); MS (ESI) m/z 328 [M+H]+, 100percent, 326 [M-H]-, 100percent. To a solution of 1-[5-(1,3-benzothiazol-6-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]methanamine (600 mg, 1.83 mmol) and NEt3 (370 mg, 3.66 mmol) in CHCl3 (15 mL) was added dropwise n-butyryl chloride (0.21 mL, 2.02 mmol) at 0 oC. The reaction mixture was stirred at 0 oC for 0.5 h. Water was added to the reaction mixture and extracted with CHCl3 twice. The combined organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with EtOAc to 10percent MeOH/CHCl3. The amorphous obtained was crystallized from EtOAc/n-Hexane to afford 20 as a yellow powder (441 mg, 61percent): mp 190.0-191.0 oC; 1H NMR (300 MHz, DMSO-d6, delta): 0.89 (t, J = 7.4 Hz, 3 H), 1.47 – 1.63 (m, 2 H), 2.14 (t, J = 7.5 Hz, 2 H), 2.34 (d, J = 0.9 Hz, 3 H), 4.36 (d, J = 5.6 Hz, 2 H), 7.15 (d, J = 0.9 Hz, 1 H), 8.08 (br s, 1 H), 8.14 (d, J = 8.5 Hz, 1 H), 8.34 (br t, J = 5.6 Hz, 1 H), 8.85 (br s, 1 H), 9.43 (s, 1 H), 12.72 (br s, 1 H); MS (ESI) m/z 398 [M+H]+, 100percent, 420 [M+Na]+, 20percent, 396 [M-H]-, 100percent; Anal. Calcd for C19H19N5OS20.2H2O: C, 56.89; H, 4.88; N, 17.46. Found: C, 57.04; H, 4.88; N, 17.17.

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
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