Month: May 2021

Electric Literature of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compound 3 was prepared by the condensation of commercially available aminoacetaldehyde diethyl acetal with the phthalic anhydride (1:1 mol ratio), using toluene under reflux, in the presence of a catalytic amount of DMAP (yield 52percent) for 2 h. In the next step, 2-(2,2-diethoxyethyl)isoindoline-1,3-dione (3) underwent acid hydrolysis (sulphuric acid at 70percent) in reflux for 2 h. After the reaction was completed, it was allowed to reach at room temperature and was then cooled to induce precipitation. The formed precipitate was filtered on a sintered funnel with distilled water, yielding 55percent of the pure product. For the synthesis of 5a and 5b, 2-(1,3-dioxoisoindol-2-yl) acetaldehyde (4) reacted with thiosemicarbazide (in the ratio 1:1) (for 5a) or 4-phenyl-3-thiosemicarbazide (for 5b), in ethanol, under reflux with catalytic amount of HCl (4 drops) for 4 h. The reactions were followed by thin layer chromatographic plate analysis. The formed precipitate was filtered on a sintered funnel with ethanol to yield the pure product (yield 76percent for 5a and 70percent for 5b). 4.1.3.1 (E)-2-[2-(1,3-dioxoisoindolin-2-yl)ethylidene]hydrazinecarbothioamide (5a) White crystals; Yield: 76percent; m.p. (¡ãC) 223-224; Rf 0.45 (hexane/ethyl acetate 3:2); IR (KBr, cm-1): 3423 and 3308 (N-H), 1769 and 1713 (C=O), 1602 (C=N); 1H NMR (300 MHz, DMSO-d6), delta ppm: 4.36 (d, J = 3.6 Hz, 2H, CH2), 7.36 (s, 1H, NH), 7.42 (t, J = 3.6 Hz, 1H, CH=N), 7.83-7.90 (m, 4H, Ar), 8.03 and 11.27 (s, 1H, NH2); 13C NMR (75.5 MHz, DMSO-d6), delta ppm: 40.1 (CH2), 123.1 (Ar), 131.7 (Ar), 134.4 (Ar), 140.4 (C=N), 167.5 (C=O), 177.9 (C=S). Anal. Calcd for C11H10N4O2S: C, 50.37; H, 3.84; N, 21.36; S, 12.22. found: C, 50.03; H, 3.45; N, 20.98; S, 12.30. HRMS: 262.3388 [M+H] +.

The chemical industry reduces the impact on the environment during synthesis N-(2-Oxoethyl)phthalimide. I believe this compound will play a more active role in future production and life.

Reference:
Article; De Moraes Gomes, Paulo Andre Teixeira; Oliveira, Arsenio Rodrigues; De Oliveira Cardoso, Marcos Verissimo; De Farias Santiago, Edna; De Oliveira Barbosa, Miria; De Siqueira, Lucianna Rabelo Pessoa; Moreira, Diogo Rodrigo Magalhaes; Bastos, Tanira Matutino; Brayner, Fabio Andre; Soares, Milena Botelho Pereira; De Oliveira Mendes, Andresa Pereira; De Castro, Maria Carolina Accioly Brelaz; Pereira, Valeria Rego Alves; Leite, Ana Cristina Lima; European Journal of Medicinal Chemistry; vol. 111; (2016); p. 46 – 57;,
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Electric Literature of 3891-07-4, These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-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.

Preparation of Ethyl 4-[2-(PHTHALIMIDO) ETHOXY] ACEFOACETATE (X1 A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 75 mL of tetrahydrofuran under nitrogen atmosphere. 7.53 g Sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 20 g of N- (2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 16.35 g ethyl 4-chloroacetoacetate in 30 ML of TETRAHYDRAFURAN was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 10 mL ethanol. The mixture was then poured into 150 mL of IN hydrochloric acid solution in crushed ice and 200 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of 5 wt. % OF NAHC03 solution, then with 150 ML of water, dried over 5 G of MgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 15 mL of hexane to remove the mineral oil to give 17.2 g of ethyl 4- [2- (phthalimido) ethoxy] acetoacetate light brown product. (yield 51%, rel. compound purity > 80%). IR (KBR, CM~L) : 2995 and 1716. 1H-NMR (CDC13) 6 7.76 (dd, 2H), 7.65 (dd, 2H), 4.11 (S, 2H), 4.02 (q, 2H), 3.80 (t, 2H), 3.70 (t, 2H), 3.37 (s, 2H), 1. 16 (t, 3H). 13C-NMR (CDC13) 8 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 61.6, 46.0, 37.4, 14.3.

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
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Electric Literature of 3676-85-5, 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 3676-85-5 as follows.

Inthe above reaction scheme, the compound6and 7 was synthesized by literature procedure[2]. To a boiling ethanol solution (10 mL) of 7 (0.2 mmol, 30 mg) was added hydrazinehydrate 50% (0.2 mmol, 1 mL). Thereaction mixture was refluxed at 80 oC for 45 min. After completionof the reaction the reaction mixture was cooled in ice water bath, theprecipitate was collected and dried in room temperature. (Color: yellow solid;Yield: 25 mg (74%)). 1H-NMR spectrum of 8(DMSO-d6, 300MHz, ppm): delta 5.73 (s, 2H), 6.53 (s, 1H), 6.56 (s,1H), 7.30 (d, J = 8.4 Hz, 2H), 7.80 (s, 1H); 13C-NMRspectrum of 8 (DMSO-d6, 75MHz, ppm): delta 157.6, 154.3, 152.9, 128.8, 117.2, 119.3, 116.5, 106.0. 1 H-NMR spectrum of 7 (DMSO-d6,300 MHz, ppm): delta 5.54, (s 2H), 6.83 (dd, J = 6.1 Hz, 1H), 6.9 (d, J = 2.1 Hz, 1H), 7.48 (d, J = 8.4Hz, 1H), 7.58 (s, 1H), 10.24 (s, 1H).FTIR spectrum of 6, 7and8, FTIR (ATR)(nu,cm-1): 3317 (N-H), 1695 (C=O), 1543,1340 (N-O), 1070, 1301 (C-O), 715 (C-H); 3440 (N-H), 1710 (C=O), 1381, 1072 (C-O),746 (C-H) and 3740 (N-H), 1640 (C=O), 1407, 1072 (C-O), 719 (C-H),respectively. UV-Visible absorption of8(c 0.564¡Á10-4 mol/ L, C2H5OH); UV (C2H5OH)lambdamax(log epsilon) 273 (1.949).

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Daniel Thangadurai; Nithya; Rakkiyanasamy; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 211; (2019); p. 132 – 140;,
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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. 480-91-1, name is Isoindolin-1-one, A new synthetic method of this compound is introduced below., Quality Control of Isoindolin-1-one

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

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; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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Reference of 3891-07-4, The chemical industry reduces the impact on the environment during synthesis 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Team, in a 50 mL round bottom flask,The thiacalix [4] arene (721 mg, 1. OO mmol) was added,N-Light ethyl phthalimide(1.75 g, 8.57 mmol),Triphenylphosphine (800 mg, 3.05 mmol),Dry tetrahydrofuran 20 mL,Ice bath,Then diethylazodicarboxylate (531 mg, 3.05 mmol) was slowly added dropwise,After the addition, the reaction was stirred at room temperature for 48h,Hot methanol 20mL by adding, cooling,Precipitation of a large number of white solid crude products,The crude product was purified by column chromatography (eluent: ethyl acetate / n-hexane, nu / nu = 1/4) to give a white product, 748 mg, in 70% yield.

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

Reference:
Patent; Guizhou university; ZENG, XI; SUN, QIANG; ZHAO, YUANHUI; MOU, LAN; (27 pag.)CN104177351; (2016); B;,
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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. 7699-18-5, name is 5-Methoxyindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 7699-18-5

General procedure: 4.4.10 (Z)-5-methoxy-3-((2-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-6-yl)methylene) indolin-2-one (5j) Compound 5j was prepared according to the method described for compound 5a, employing aldehyde 11c (145 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81, 0.5 mmol) to obtain the pure product 5j as a yellow solid (132 mg, 61%); mp: 293-295 C; IR (KBr): 3420, 3160, 2355, 1672, 1618, 1470, 1328, 1113, 1015, 915, 845, 741 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.48 (bs, 1H), 9.22 (s, 1H), 8.44 (d, J = 8.1 Hz, 2H), 8.17 (s, 1H), 7.99 (s, 1H), 7.96 (d, J = 8.1 Hz, 2H), 7.72 (d, J = 8.3 Hz, 1H), 7.45 (s, 1H), 6.87-6.68 (m, 2H), 3.79 (s, 3H); 13C NMR (75 MHz, CDCl3 + DMSO-d6): delta 168.8, 154.6, 153.8, 138.4, 137.3, 136.4, 134.0, 133.4, 127.2, 126.6, 125.9, (q, J = 2.7 Hz), 125.2, 125.0, 122.9, 121.9, 114.9, 110.2, 109.6, 108.6, 105.5, 55.2; MS (ESI): m/z 436 [M + H]+; HRMS (ESI): calcd for C24H17ON3F3 m/z 436.12073 [M + H]+; found 436.12437.

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; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
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Electric Literature of 5181-35-1, 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 5181-35-1 as follows.

To a solution of 2-(2- bromoethoxy)isoindoline-l,3-dione (20 g, 74 mmol) in dimethylformamide (100 ml) added 5-(2- tertiary-butyl-dimethyl-silanyloxy ethyl)- lH-tetrazole (14.81 g, 74 mmol) at 25-30 C under stirring followed by cesium carbonate ((29 g, 88 mmol) in portion wise under stirring. The reaction was continued further at same temperature for 16 hrs and filtered. The filtrate was slowly poured onto chilled water (700 ml) under stirring and continued stirring for 30 minutes. The formed precipitates were filtered and washed with water (70 ml). The solid compound was dried at 40 C for 2 hour under high vacuum to yield crude compound 17.2 g. The crude compound was column purified (silica gel 60-120 mesh size) using hexane and acetone as an eluent. The non-polar spot isolated at 8-12% concentration of acetone in hexane, yielded 8 g of 2-{2-[5-(2-tertiary-butyl- dimethyl-silanyloxy ethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione. The polar spot was isolated at 16-20% concentration of acetone in hexane and yielded 4.2 g of 2-{2-[5-(2-tertiary- butyl-dimethyl-silanyloxy ethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)-dione as white solid. Analysis: Mass: 418.3 (M+H); for Molecular weight: 417 and Molecular formula: Ci9H27N504Si. 1HNMR (CDCI3): delta.83-7.74 (m, 4H), 5.00 (t, 2H, J=6 Hz), 4.73 (t, 2H, J=6 Hz), 3.98 (t, 2H, J=6.8 Hz), 3.08 (t, 2H, J=7.2 Hz), 0.837 (s, 9H), 0.002 (s, 6H).

According to the analysis of related databases, 5181-35-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 5394-18-3

To a cooled solution of 1 /-/-imidazole (200 mg, 3.085 mmol, 1.05 eq) in DMF (7 ml_), NaH 60% in mineral oil (136 mg, 3.393 mmol, 1.1 eq.) was added portionwise and the mixture was stirred for 10 min. Afterwards, a solution of 2-(4-bromobutyl)-2,3-dihydro-1 7Aisoindole-1,3-dione (870 mg, 3.085 mmol, 1 eq.) in DMF (3 ml.) was added dropwise. The reaction was continued at 60C for further 16 h. The reaction was quenched with water and diluted in AcOEt. The layers were separated. Organic layer was dried, filtered off and concentrated in vacuo. The residue was purified by FCC (SiHP, DCM: MeOH 95:5) to afford the title compound (323 mg, 1.2 mmol, yield 40%) as a white solid. ESI-MS: 270 [M+H]+ 1H NMR (300 MHz, Chloroform-o) d 7.89 – 7.85 (m, 2H), 7.77 – 7.73 (m, 2H), 7.50 (t, J= 1.1Hz, 1H), 7.07 (t, J= 1.1Hz, 1H), 6.93 (t, J= 1.3 Hz, 1H), 4.02 (t, J= 7.0 Hz, 2H), 3.74 (t, J= 6.8 Hz, 2H), 1.91 – 1.79 (m, 2H), 1.78 – 1.64 (m, 2H).

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; RYVU THERAPEUTICS S.A.; DOBRZANSKA, Monika Patrycja; ZAWADZKA, Magdalena Izabela; RADZIMIERSKI, Adam; TOPOLNICKI, Grzegorz Witold; CWIERTNIA, Grzegorz Wojciech; MAHAJAN, Tushar Ravindra; FABRITIUS, Charles-Henry; CHMIELEWSKI, Stefan; GLUZA, Karolina Maria; ALVAREZ, Jose; ROGACKI, Maciej Krzysztof; MROCZKOWSKA, Magdalena; (215 pag.)WO2019/238786; (2019); A1;,
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317-20-4, name is 7-Fluoroisatin, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C8H4FNO2

Weigh rapamycin (0.05mmol), isatin 3j (0.10mmol) and rhodium octanoate dimer(0.0005mmo),They were placed in a reaction flask, 2.0 mL of dry dichloromethane was added, and after stirring at room temperature for 5 minutes,Phenyldiazo 2a (0.10 mmol) was weighed and dissolved in dry dichloromethane (1.0 mL), and slowly added dropwise to the reaction system (about 1 hour), and stirring was continued for half an hour.The solvent was removed by rotary evaporation to give a crude product. The rapamycin analog I-j was obtained by column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 to 1:4).The yield was 85%.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ha Yao Cihang Pharmaceutical Co., Ltd.; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Duan Yanwen; Huang Yong; Qiu Lin; Wen Zhongqing; Su Meng; (38 pag.)CN109776571; (2019); A;,
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20780-72-7, name is 4-Bromoisatin, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 4-Bromoisatin

To 4-bromoindoline-2,3-dione (200 mg, 0.89 mmol) in 5 ml DMF was added 4- Fluorobenzylbromide (0.120 ml, 0.98 mmol) then add NaH (35 mg, 0.89 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 270 mg (90percent) of product.

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

Reference:
Patent; SCHERING CORPORATION; WO2009/73777; (2009); A1;,
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