Category: indolines-derivatives

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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(2-Hydroxyethyl)isoindoline-1,3-dione

PREPARATION 7 Preparation of ethyl 4-[2-(phthalimido)ethoxy]acetoacetate STR52 Sodium hydride (57% [by weight] in oil, 66.1 g) was stirred in dry tetrahydrofuran (500 ml) under nitrogen at -10 while N-(2-hydroxyethyl)phthalimide (150 g) was added. To this slurry was added at -10 a solution of ethyl 4-chloroacetoacetate (129.3 g), in dry tetrahydrofuran, over 1 hour. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 18 hours. This mixture was poured into 1N hydrochloric acid (800 ml) and ethyl acetate was added (750 ml). The aqueous layer was washed with ethyl acetate (300 ml) and the organic solutions were combined. After washing with water (300 ml), the ethyl acetate was evaporated to give the title compound as a crude oil (243 g), sufficiently pure for further use.

According to the analysis of related databases, 3891-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US4572909; (1986); 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 32692-19-6 as follows. Recommanded Product: 32692-19-6

Example 33: 4-(5-Nitroindolin-1 -yl)phenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranosideTo a mixture of 4-iodophenyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside (18, 200 mg, 0.37 mmol), Cs2C03 (364 mg 1 .12 mmol) and 5-nitroindoline (91 .6 mg, 0.56 mmol) in a Schlenk tube under argon, x-Phos (9.1 mg, 0.019 mmol) and Pd2(dba)3 (3.85 mg, 0.0037 mmol), which had been pre-stirred for 15 min at 40C in dry toluene (3.5 mL), are added. The reaction mixture is degassed in an ultrasonic bath and stirred 140 h at 80C. The reaction mixture is diluted in EtOAc (50 mL) and washed with aqueous satd. NaHC03 solution (2 x 50-100 mL) and brine (50-100 mL). The aqueous layers are each extracted with EtOAc (2 x 50-100 mL) and the combined organic layers are dried over Na2S04, filtered and concentrated under reduced pressure. 20 (163 mg, 75%) is obtained as an orange solid after silica gel chromatography (5-40% gradient of EtOAc in petrol ether). [a]D20 +55 (c = 1 , CHCIs); 1H NMR (CDCI3): delta 2.02 (s, 3H, OAc), 2.04 (s, 6H, 20Ac), 2.18 (s, 3H, OAc), 2.20 (s, 3H, OAc), 3.19 (t, J = 8.6 Hz, 2H, CH2), 4.08 (m, 4H, CH2, H-6a, H- 5), 4.28 (dd, J = 5.2, 12.5 Hz, 1 H, H-6b), 5.38 (t, J = 10.1 Hz, 1 H, H-4), 5.44 (dd, J = 1.8, 3.5 Hz, 1 H, H-2), 5.50 (d, J = 1 .6 Hz, 1 H, H-1 ), 5.55 (dd, J = 3.5, 10.1 Hz, 1 H, H-3), 6.73 (d, J = 8.9 Hz, 1 H, C6H4, C6H3 ) 7.13 (m, 3H, C6H4, C6H3 ), 7.21 (m, 1 H, C6H4, C6H3), 7.95 (s, 1 H, C6H3, C6H4 ), 7.98 (dd, J = 2.3 Hz, 8.9 Hz, 1 H, C6H3, C6H4 ); 13C-NMR (CDCI3): delta 20.90, 20.92, 21 .09, 21 .65 (40Ac), 27.27 (CH2), 53.85 (CH2), 62.28 (C-6), 66.03 (C-4), 68.98 (C-3), 69.40 (C-2), 69.53 (C-5), 96.36 (C1 ), 105.52 (C6H4), 1 17.81 ,1 17.92 (C6H4, C6H3), 121 .32 (C6H3), 122.03 (C6H4), 126.27 (C6H3), 128.40 (C6H3), 137.21 (Car-N) , 169.90, 170.19, 170.23, 170.70 (C=0); ESI-MS calcd. for C28H31N20i2 [M+H]+: 587.19; found 587.29.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; HEROLD, Janno; WO2011/73112; (2011); A2;,
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Reference of 3339-73-9, 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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, This compound has unique chemical properties. The synthetic route is as follows.

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 chemical industry reduces the impact on the environment during synthesis 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Rani, Anu; Legac, Jenny; Rosenthal, Philip J.; Kumar, Vipan; Bioorganic Chemistry; vol. 88; (2019);,
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Related Products of 6326-79-0, A common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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 solution of 6-bromoisatin (10 g, 22 mmol) in IN aqueous NaOH solution (48 mNo.) was stirred at 50 0C for 1 h. The mixture was cooled to 0 0C Sodium nitrite (3 g, 22 mmol) solution in water (11 m-6) was added drop wise for 15 min at 0 0C The mixture was added to the solution of water (90 mNo.) and sulfuric acid (4.6 mNo.) at 0 0C for 15 min. The mixture was added to the solution of cone, hydrochloric acid (40 m-6) and SnCl2.2H 2O (24 g, 53 mmol). After 1 h, the mixture was filtered and washed with water. The solid was dried through air flow to give the titled compound (8.98 g).[185] [186] 1H NMR (300 MHz, DMSOd6) delta 13.76 (bs, IH), 7.87 (s, IH), 7.55 (d, J = 8 Hz, IH), 7.27 (d, J = 8 Hz, IH), 2.44 (s, 3H).

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; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; SIM, Tae Bo; SON, Jung Beom; KIM, Hwan; PARK, Dong Sik; CHOI, Hwan Geun; HAM, Young Jin; HAH, Jung Mi; YOO, Kyung Ho; OH, Chang Hyun; LEE, So Ha; HA, Jae Du; CHO, Sung Yun; KWON, Byoung-Mog; HAN, Dong Cho; WO2010/64875; (2010); A2;,
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Related Products of 2058-74-4, 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 2058-74-4 as follows.

General procedure: Amultimodereactor (Synthos 3000 Anton Paar, GmbH, 1400Wmaximum magnetron) was used. The initial step was conductedwith 4-Teflon vessels rotor (MF 100) that allowsthe reactions to process under the same conditions. Isatinderivatives 1a-1f and hydrazine hydrate 2a, thiosemicarbazide2b, or 4-aminobenzamide 2c were mixed together ina small portion of ethanol and then subjected to microwaveirradiation (400 watt). The vessels were heated for 5 min at100?C and held at the same temperature for another 5min.cooling was accomplished by a fan (5 min).The final productwas washed with cold ethanol and then dried under vacuumto afford the products 3a-3n in high yield and purity.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; El-Faham, Ayman; Hozzein, Wael N.; Wadaan, Mohammad A. M.; Khattab, Sherine N.; Ghabbour, Hazem A.; Fun, Hoong-Kun; Siddiqui, Mohammed Rafiq; Journal of Chemistry; vol. 2015; (2015);,
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Reference of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 × 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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Some common heterocyclic compound, 21544-81-0, name is 4,6-Dimethoxyindoline-2,3-dione, molecular formula is C10H9NO4, 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: 21544-81-0

A solution of 4,6-dimethoxyindoline-2,3-dione(0.6g, 2.89 mmol) in NaOH (33% in water, 38 mL) was headedto 70 C. H2O2(30% in water, 9.4 mL) was added to the solutiondropwise. Themixture was maintained at 70 C for 40 min. Saturated Na2S2O3solution (30 mL) was added to the abovemixture at 10 C. The reactionmixture was adjusted to pH 8with HCl and then to pH 5 with AcOH. Theprecipitate thatformed was collected, washed with water, and dried to give compound11 (188 mg, 33%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21544-81-0, its application will become more common.

Reference:
Article; Shao, Mingfeng; He, Linhong; Zheng, Li; Huang, Lingxiao; Zhou, Yuanyuan; Wang, Taijing; Chen, Yong; Shen, Mingsheng; Wang, Fang; Yang, Zhuang; Chen, Lijuan; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4051 – 4055;,
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Related Products of 20780-72-7, A common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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 3 Suzuki Coupling of 4-bromoindoline-2,3-dione Derivatives with Trifluoroborate Potassium Salts [0344] 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3PO4 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2Cl2 or Pd(dppf)2Cl2 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130° C. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL/mmol substrate) and filtered through Celite®. The organic solution was washed with brine (10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product which was purified as specified below. 4-(o-Tolyl)indoline-2,3-dione Following General Procedure 3,4-bromoisatin (100 mg, 0.44 mmol), potassium 2-methyphenyltrifluoroborate (123 mg, 0.62 mmol), K3PO4 (338 mg, 1.59 mmol) and Pd(PPh3)2Cl2 (31 mg, 0.04 mmol) in THF/H2O (3:1, 3 mL) gave the crude reaction mixture, which was purified via flash column chromatography (eluent 30-40° C. petrol/acetone, 4:1) to afford the product as an orange solid (65 mg, 59percent). deltaH (500 MHz, DMSO-d6) 2.15 (3H, s), 6.93 (2H, m), 7.14 (1H, d, J=7.6 Hz), 7.20-7.26 (1H, m), 7.30 (1H, d, J=7.3 Hz), 7.32-7.37 (1H, m), 7.56 (1H, app t, J=7.9 Hz), 8.84 (1H, br s) deltaC (125 MHz, DMSO-d6) 19.7, 111.2, 115.7, 125.6, 126.3, 128.6, 128.8, 130.1, 135.7, 136.4, 137.9, 142.8, 149.3, 159.2, 182.0 mp 161-162° C.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); A1;,
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Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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 solution of isatins 1 (0.6 mmol), isatylidenyl-chromanones 2 (0.4 mmol), and sarcosine (0.8 mmol) in the 12.0 mL of MeOH at reflux for the specified reaction time and monitored by TLC. Then they were concentrated in vacuo to yield the crude products, which were further purified by column chromatography on silica gel (hexane/EtOAc 8:1 3:1) to give the desired products 3.

Statistics shows that 5-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 2058-72-2.

Reference:
Article; Gong, Yi; Wang, Guan-Lian; Wei, Qi-Di; Chen, Lin; Liu, Xiong-Li; Tian, Min-Yi; Yang, Jun; Feng, Ting-Ting; Zhou, Ying; Synthetic Communications; vol. 48; 9; (2018); p. 1016 – 1024;,
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These common heterocyclic compound, 59-48-3, name is Indolin-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. HPLC of Formula: C8H7NO

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and 3.2 mL acetyl chloride were slowly added. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration, washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of the title compound as a brown solid.

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

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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