Author: Jessica.F

Reference of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of isatin (1 mmol), dicarbonyl compound 1 (1 mmol),dicarbonyl compound 2 (1 mmol) and SSLP (0.1 g, 4.8 mol%) wasadded to a 25 mL canonical flask contained water (5 mL) and was stirred at 80 C for appropriate time. After completion of the reac-tion as indicated by TLC, the reaction mixture was filtered and washed with acetone (25 mL, two times) to separate the catalyst.The obtained organic phase was evaporated and the residue was recrystallized from ethanol to obtain the pure products.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Khalafi-Nezhad, Ali; Shahidzadeh, Elham Shaikhi; Sarikhani, Samira; Panahi, Farhad; Journal of Molecular Catalysis A: Chemical; vol. 379; (2013); p. 1 – 8;,
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Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-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 6941-75-9, name: 5-Bromoisoindoline-1,3-dione

A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g, 0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bro moisoindoline-1,3-dione (5 g, 22 mmol) was added at the same temperature over the period of 30 min The reaction mixture was stirred at 0 C. for 30 min and 3 h at ambient temperature. The reaction mixture was filtered and the filtrate was neutralized with concentrated HCl. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261 C.; 1H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J=9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]-); IR (thin film) 1684, 3246, 606 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171308; (2014); 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 24566-79-8 as follows. COA of Formula: C14H16BrNO2

General procedure: A mixture of the corresponding secondary amine 3a-d [23] (5.5mmol), anhydrous K2CO3 (6mmol) and compounds 2a-d (5mmol) were added in CH3CN (20ml). The mixture was heated at 65C for 8-10h. The solvent was evaporated under reduced pressure. Then water (25mL) was added, and the mixture was extracted with dichloromethane (20mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30mL), dried over sodium sulfate, and filtered. The solvent was evaporated under vacuum. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to obtain the oil products 4-7.

According to the analysis of related databases, 24566-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sang, Zhipei; Qiang, Xiaoming; Li, Yan; Xu, Rui; Cao, Zhongcheng; Song, Qing; Wang, Ting; Zhang, Xiaoyu; Liu, Hongyan; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 135; (2017); p. 307 – 323;,
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Electric Literature of 24566-79-8,Some common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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: Amixture of the corresponding secondary amine 7a-d (5.5 mmol), anhydrous K2CO3 (6 mmol) andcompounds 2-4 (5 mmol) was added inCH3CN (20 ml). The mixture was heated at 65 C for 8-10 h. Thesolvent was evaporated under reduced pressure. Then water (25 mL) was added,and the mixture was extracted with dichloromethane (20 mL × 3). The combinedorganic phases were washed with saturated aqueous NaCl (30 mL), dried oversodium sulfate, and filtered. The solvent was evaporated under a vacuum. The residue was purified on a silicagel chromatography using mixtures of petroleum/acetone as eluent to obtain theoil products 8-10.

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

Reference:
Article; Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2539 – 2543;,
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Application of 20870-79-5, A common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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.

The derivatives 1 -5 were synthesized following the synthetic procedure reported in scheme 1 of Figure 1 . The 5-nitro-1 ,3-dihydro-2/-/-indol-2-one commercial compound was reduced to the corresponding 5-amino-1 ,3-dihydro-2H-indol-2-one by means of catalytic hydrogenation using Pd/C as a catalyst. The subsequent reaction with the chloro acetyl chloride provided 2-chloro-/V-(2-oxo-2,3-dihydro-1 /-/-indol-5-yl)acetamide which was condensed with the appropriate amine derivative to provide, respectively, 2-[(6,7-dimethoxy-3,4-dihydroisoquinol-2-(1 H)-yl)]-N-(2-oxo-2,3- dihydro-1 H-indol-5-yl)acetamide and 2-[(3,4-dimethoxybenzyl)amino]-/V-(2-oxo- 2,3-dihydro-1 /-/-indol-5-yl)acetamide. Lastly, condensation of the appropriate aromatic carbaldehyde in the presence of pyrrolidine provided the desired products 1 -5.

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; INTERNATIONAL SOCIETY FOR DRUG DEVELOPMENT S.R.L.; RAPPOSELLI, Simona; MARTINI, Claudia; CALDERONE, Vincenzo; PURICELLI, Guido; (30 pag.)WO2016/55454; (2016); A1;,
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Electric Literature of 25369-33-9,Some common heterocyclic compound, 25369-33-9, name is 7-Chloroindolin-2-one, molecular formula is C8H6ClNO, 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: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

The synthetic route of 25369-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
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Electric Literature of 3339-73-9, 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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1.0 mmol of (1,3-dioxoisoindolin-2-yl) acid, N-ethyl-N-dimethylaminopropylcarbodiimide (EDC) (1.1 mmol), hydroxybenzotriazole(HOBt) (1.2 mmol) and N,N-Diisopropylethylamine (2.0 mmol) weremixed in minimum DMF and the obtained mixture was stirred for5 min. Then, 4-aminoquinoline-diamines (1.0 mmol) was added to thereaction mixture and the stirring was continued for 5 h. The reactionend was proved by thin layer chromatography (TLC). Then, DMF wasevaporated using rotary evaporator and cold water (20 mL) was added,and solid precipitates obtained were filtered and washed with coldwater. The crude product was recrystallized in absolute ethanol.

The synthetic route of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rani, Anu; Legac, Jenny; Rosenthal, Philip J.; Kumar, Vipan; Bioorganic Chemistry; vol. 88; (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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Quality Control of 6-Bromoisoindolin-1-one

Compound WX005-3 (1.00 g, 4.72 mmol, 1.00 eq), compound WXBB-1 (1.53 g, 14.15 mmol, 3.00 eq), cuprous iodide (89.82 mg, 471.61 mumol, 0.10 eq), potassium carbonate (1.96 g, 14.15 mmol, 3.00 eq), and tetramethylethylenediamine (54.81 mg, 471.61 mumol, 71.18 muL, 0.10 eq) were dissolved in toluene (10.00 mL). The mixture was purged with nitrogen three times, and then reacted at 130 C. for 16 hours under a nitrogen atmosphere. After the reaction was completed, the reaction solution was added with methanol (15 mL), and filtered, followed by concentrating of the filtrate. The crude product was separated and purified by prep-HPLC (column: Phenomenex Gemini 150*25 mm*10 mum; mobile phase: [water (0.05% HCl)-ACN]; B %: 0-30 (10 min) %-30-55 (4 min) %, 14 min). Compound WX005-4 was obtained, 1H NMR (400 MHz, METHANOL-d4) delta ppm 8.07 (s, 1H), 7.89 (s, 1H), 7.80-7.83 (m, 1H), 7.72-7.74 (m, 1H), 7.384 (s, 1H), 4.53 (s, 2H), 1.90-1.95 (m, 1H), 0.89-0.93 (m, 2H), 0.76-0.78 (m, 2H). MS m/z: 239.9 [M+H]+.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIAN COSUNTER PHARMACEUTICAL CO., LTD.; Wu, Chengde; Yu, Tao; Li, Ning; Chen, Shuhui; US2019/375728; (2019); A1;,
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Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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: 169037-23-4

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(p-chlorophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(p-chlorophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5f): Melting point 259-261 C; white solid, 95%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.60 (d, J = 13.92 Hz, 1H), 4.18-4.23 (m, 1H), 3.86 (d, J = 10.28 Hz, 1H), 3.24-3.38 (m, 2H), 2.92-3.00 (m, 2H), 2.50-2.54 (m, 1H), 2.33-2.39 (m, 1H), 6.53-6.56 (m, 2H), 6.67-7.02 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.8, 46.9, 52.3, 53.1, 61.5, 65.9, 70.7, 100.4, 109.8, 123.9, 124.1, 126.0, 128.1, 128.2, 128.4, 128.7, 128.8, 129.0, 130.4, 131.4, 132.5, 132.6, 135.8, 135.9, 136.4, 140.6, 143.7, 136.2, 137.6, 138.5, 139.9, 144.4, 179.1, 196.9. EI-MS: m/z 780 (M+). Anal. Calcd for C44H34Cl2F3N3O3: C, 67.70; H, 4.39; N, 5.38; Found: C, 67.59; H, 4.51; N, 5.25.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 169037-23-4, its application will become more common.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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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. 74572-29-5, name is 5-Chloroisoindolin-1-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H6ClNO

[A] 2-(8-Amino-5,6,7,8-tetrahydro-isoquinolin-4-yl)-5-chloro-2,3-dihydro-isoindol-1-one In a 25 mL sealed tube, 5-chloro-2,3-dihydro-isoindol-1-one (80.1 mg, 4.8 mmol), 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-ylamine (intermediate B-12 [A], 999 mg, 4.4 mmol), CuI (200 mg, 1.1 mmol), Cs2CO3 (3.0 g, 9.2 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.4 mL, 3.2 mmol) were dissolved in dioxane (16 mL). The resulting reaction mixture was heated at 150 C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2*125 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (1.2 g, 80%) as a light yellow solid. MS: 314.2 (M+H+).

The synthetic route of 74572-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Aebi, Johannes; Amrein, Kurt; Chen, Wenming; Hornsperger, Benoit; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Wang, Zhanguo; Zhou, Mingwei; US2013/143863; (2013); A1;,
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