Category: 3891-07-4

Reference 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.

EXAMPLE 1 Preparation of Ethyl 4-(2-(Phthalimido)Ethoxy)Acetoacetate (Formula V) 300 liters of toluene was taken into a clean and dry reactor and 50 Kg of sodium hydride was added under a nitrogen atmosphere. 50 Kg of [N-{2-hydroxyethyl}] phthalimide was added to the reactor and the resultant reaction mass was subjected to agitation and heating to 57 C. The reaction mass was maintained at 56-57 C. for 30 minutes. Another 50 Kg of [N-{2-hydroxyethyl}] phthalimide was added to the above reaction mass in 18 lots of 2.7 kg each and a further lot of 1.4 kg, at 60 C. Liberation of hydrogen was observed. The reaction mass was maintained at 57 C. until hydrogen gas liberation ceased. A solution of 94 Kg of ethyl 4-chloroacetoacetate in 287 liters of toluene was added to the above reaction mass at 57 C. and maintained at the same temperature for 20 minutes. The reaction mass was then cooled to 30 C. and then further cooled to 17 C. 200 liters of glacial acetic acid was added to the above obtained reaction mass in three equal lots at 17 C. and stirred for 30 minutes. 1000 liters of water was added to the reaction mass and stirred for 20 minutes. The organic layer was separated and the aqueous layer was extracted into 220 liters of toluene. The combined toluene layer was progressed to the next stage.

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

Reference:
Patent; Bolugoddu, Vijayabhaskar; Dahyabhai, Jaydeepkumar Lilakar; Pingili, Ramachandra Reddy; Veeraboina, Madhu Raju; Gade, Srinivas Reddy; Mallepalli, Srinivas Reddy; Amirisetty, Ravindranath Tagore; US2007/260065; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 3891-07-4

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 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; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, 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. Recommanded Product: 3891-07-4

Into the reaction tank, put 350 kg of toluene, stirring temperature, distillation of toluene, after the liquid in the water separator is filled, keep the reflux water for 60 minutes, and take a sample to measure the water, when the water content of the reflux liquid is ?0.2%, the reflux is changed to distillation, distilled 45kg of toluene (worked ethyl 4-chloroacetoacetate as a dilution solvent), stirring and lowering the temperature, when the temperature in the tank drops to 45 C, the reaction tank is filled with nitrogen, continue to cool down at-5 C, under stirring add 40 kg of N-(2-hydroxyethyl)-phthalimide, and the add 20 kg of sodium hydride, after the addition, cover the can lid, stirring at -5 C, into the metering tank draw 38.4 kg of ethyl 4-chloroacetoacetate, 45 kg of toluene and mix well, at -5 C condition added the drops of ethyl 4-chloroacetoacetate toluene solution, the dropping time is controlled at 4 hours, after the addition, the reaction is stirred and the temperature is slowly increased, the temperature of the reaction solution is slowly raised at 32 C within 5 hours, the reaction time is more than 12 hours, and the temperature is raised at 45 C to continue the heat preservation, until the reaction is complete, cool down, control the internal temperature of 25 C, add 61 kg of glacial acetic acid, after the addition, continue stirring to make the material in the reaction solution stir evenly, and the internal temperature is controlled at 25 C, add 180kg of water, add, continue to stir for 30 minutes, stop nitrogen filling, stop stirring, let stand, divide the water layer into the barrel and transfer the toluene layer to the washing tank, transfer the water layer into the reaction tank, into the reaction tank add 75kg of toluene, stir and let stand, the water layer is separated into barrels, and the toluene layer is transferred to a washing tank, the water layer is transferred into the reaction tank, 75 kg of toluene is added into the reaction tank, stirred, and allowed to stand, and the water layer was separated, combine the toluene layer into a water wash tank, add 100kg of 25% salt water to the washing tank, stir for 15 minutes, let stand for 30 minutes, and separate the water layer, obtained 4-[(2-phthalimido) ethyoxyl] ethyl acetoacetate toluene solution

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

Reference:
Patent; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Gao Huanhuan; Liu Lijuan; Yu Yaoying; (12 pag.)CN108358833; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 3891-07-4

(i) Preparation of Ethyl-4-(2-phthalimidoethoxy)acetoacetate STR141 To a slurry of sodium hydride (57% dispersion in oil, 66.1 g; 1.57M), in tetrahydrofuran (500 ml) cooled to 0 under nitrogen was added B 2-phthalimidoethanol (150 g; 0.785M) followed by ethyl 4-chloroacetoacetate (129 g; 0.785M) in tetrahydrofuran (250 ml) over 1 hour. The mixture was stirred at room temperature overnight then poured into a mixture of 1M hydrochloric acid (800 ml) and ethyl acetate (750 ml). The organic phase was separated and the solvent was evaporated at reduced pressure. The residue separated into two layers and the upper layer of mineral oil was removed to leave the title compound (243 g) as a crude product which was used without further purification.

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; Pfizer Inc.; US4572908; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Compound 1 (2.0 g, 1.05 mmol)And compound 2 (2.3g, 1.7mmol)Add to DMA (20ml) solution,Heat the solution to 40 C,Then slowly add sodium tert-butoxide (1.6 g, 1.6 mmol),The reaction was stirred at 40 C for 3 hours.After the reaction is completed, cool to room temperature.Then slowly add acetic acid to adjust the pH to about 7,Add 10ml of water,Extracted with dichloromethane (50ml × 3),Combined organic phases,Dried over anhydrous sodium sulfate,The concentrated solution was subjected to column separation (eluent: petroleum ether / ethyl acetate (v / v) = 10: 1),To give 2.1 g of a white solid,The yield was 72%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Hydroxyethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Liu Zhiqiang; Li Huanyin; (38 pag.)CN110317211; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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 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.

Statistics shows that 2-(2-Hydroxyethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 3891-07-4.

Reference:
Patent; Pfizer Inc.; US4572909; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3891-07-4, 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 3891-07-4 as follows.

General procedure: To the stirred solution of hydroxyderivatives (0.1 mol) in anhydrous DMF (50 mL) sodiumhydride (60% in mineral oil) (4.4 g, 0.11 mol) was added with mechanistic stirring between -5 and0 C. After addition, stirring was continued for 2 h at room temperature. Carbon disulfide (9 mL,0.15 mol) was added dropwise at 0 C. The reaction mixture was warmed to room temperature andstirred for 5 h. The color of the one was gradually changed to dark red. The reaction mixture wascooled to 0 C and methyl iodide (7.8 mL, 0.12 mol) was added dropwise. The mixture was warmed toroom temperature, stirred for 3 h until the color changed from dark red to yellow and poured into ice(100 g), extracted with CH2Cl2 (3 50 mL). The extract was washed with water (3 50 mL) and driedwith MgSO4. After removal of the solvent the product was washed with hexane and dried in vacuum.3.2.1. O-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl] S-Methyl Dithiocarbonate 1dYield 27.8 g (99%). Yellow powder: mp 105-106 C. 1H-NMR (400 MHz, CDCl3): delta 2.49 (s, 3H, SCH3),4.10 (t, 3J = 5.6 Hz, 2H, CH2), 4.82 (t, 3J = 5.6 Hz, 2H, CH2), 7.71-7.73 (m, 2H, arom H), 7.83-7.86 (m, 2H,arom H). 13C-NMR (125 MHz, DMSO-d6): delta 18.4 (s, SCH3), 36.3 (s, CH2), 70.6 (s, CH2), 123.2 (s, arom.C), 131.6 (s, arom. C), 134.6 (s, arom. C), 167.7 (s, C=O), 215.2 (s, C=S). LC-MS, m/z: 282 [M + H]+.Anal. calcd for C12H11NO3S2: C, 51.23; H, 3.94; N, 4.98; S, 22.79; found: C, 51.30; H, 4.00; N, 4.98; S,22.70.

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:
Article; Sokolenko, Taras M.; Dronkina, Maya I.; Magnier, Emmanuel; Yagupolskii, Lev M.; Yagupolskii, Yurii L.; Molecules; vol. 22; 5; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Under nitrogen, to a cooled (0 C) solution of Ph3P (9.44 g, 36 mmol) in dry THF (60 mL), diisopropylazodicarboxylate (DIAD) (7.08 mL, 36 mmol) was added dropwise at stirring. The suspension obtained was stirred for 30 min and then a suspension of calixarene 9 (1:1 p-xylene complex, 6.40 g, 6 mmol) and 2-hydroxyethylpthalimide (6.88 g, 36 mmol) in THF (200 mL) was added dropwise. The stirring was continued for 1 h at low temperature and then for 24 h at room temperature. The reaction mixture (clear solution) was concentrated in vacuo to an oil, which was triturated with methanol. The solid formed was separated, washed with methanol and dried. Yield 89% (6.98 g, white powder). Mp 234-236 C (decomp.). 1H NMR (400 MHz, CDCl3) delta 7.93 (4H, m, ArHPht), 7.70 (4H, m, ArHPht), 6.96 (4H, s, ArH), 6.67 (4H, s, ArH), 6.65 (2H, s, OH), 4.44 (4H, t, J=6.6 Hz, NCH2), 4.24 (4H, t, J=6.6 Hz, OCH2), 4.18 (4H, d, J=2.9 Hz, ArCH2Ar), 3.25 (4H, d, J=12.9 Hz, ArCH2Ar), 2.10-1.35 (60H, m, HAd). 13C NMR (100 MHz, CDCl3) delta 168.10 (CO), 150.47, 149.01, 146.87, 141.49 (CAr), 133.83 (CHAr,Pht), 132.13, 132.09 (CAr), 127.72 (CAr,Pht), 124.96, 124.26 (CHAr), 123.22 (CHAr,Pht), 71.79 (OCH2), 43.70, 42.74 (CAd), 37.47 (NCH2), 36.91, 36.61 (CAd), 35.29, 35.26 (CAd), 31.11 (ArCH2Ar), 29.08, 28.76 (CHAd). FD-MS: m/z 1308.5 [M+H]+; C88H94N2O8·H (1308.7).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Hydroxyethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Article; Vatsouro, Ivan; Serebryannikova, Alina; Wang, Leyong; Hubscher-Bruder, Veronique; Shokova, Elvira; Bolte, Michael; Arnaud-Neu, Franoise; Boehmer, Volker; Kovalev, Vladimir; Tetrahedron; vol. 67; 42; (2011); p. 8092 – 8101;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. HPLC of Formula: C10H9NO3

(i) Preparation of Ethyl-4-(2-phthalimidoethoxy)acetoacetate STR141 To a slurry of sodium hydride (57% dispersion in oil, 66.1 g; 1.57M), in tetrahydrofuran (500 ml) cooled to 0 under nitrogen was added B 2-phthalimidoethanol (150 g; 0.785M) followed by ethyl 4-chloroacetoacetate (129 g; 0.785M) in tetrahydrofuran (250 ml) over 1 hour. The mixture was stirred at room temperature overnight then poured into a mixture of 1M hydrochloric acid (800 ml) and ethyl acetate (750 ml). The organic phase was separated and the solvent was evaporated at reduced pressure. The residue separated into two layers and the upper layer of mineral oil was removed to leave the title compound (243 g) as a crude product which was used without further purification.

The synthetic route of 2-(2-Hydroxyethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4572908; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-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 3891-07-4, category: indolines-derivatives

To a solution of N-(2-hydroxyethyl)phthalimide (2g, 10.5mmol) in anhydrous tetrahydrofuran (30mL) was added 60% NaH (0.84 g, 21 mmol) at -5C. The mixture was stirred at the same temperature for 20 min. Commercially available 4b (1.5 mL, 12.6 mmol) was added to the mixture and was stirred at the same temperature for 30 min and then stirred at room temperature for 4 h and filtered. The filtrate was concentrated under reduced pressure to give 5b (2.65 g, 90%) as a off-white solid.

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:
Article; Wang, Minghua; Ye, Cheng; Liu, Mingliang; Wu, Zhaoyang; Li, Linhu; Wang, Chunlan; Liu, Xiujun; Guo, Huiyuan; Bioorganic and Medicinal Chemistry Letters; vol. 25; 14; (2015); p. 2782 – 2787;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem