Category: 118-29-6

Redox catalysis has been broadly utilized in electrochemical synthesis. The appropriate choice of redox mediator can avoid electrode passivation and overpotential, which strongly inhibit the efficient activation of substrates in electrolysis., Application of 118-29-6

To a mixture of compound 2,3,3-Trimethylindolenine (1) (2.0 g, 12.5 mmol, 1.1 eq.) and A (Hydroxymethyl)phthalimide (3) (2.02 g 11.4 mmol, 1 eq.) were added 14.7 mL of concentrated sulfuric acid and the system stirred at room temperature for 6 days. The reaction was then poured over ice and made basic with concentrated aqueous ammonium hydroxide. After crystallizing at -20 C overnight, the resulting precipitate was filtered, rinsed with ice cold water, and dried under vacuum to give indolenine 4 as a light yellow shiny crystalline solid. Yield 88.3%. XH NMR (400 MHz, CDCl3); d 7.82-7.87 (m, 2H, Ar- H); 7.67-7.72 (m, 2H, Ar-H); 7.44-7.48 (m, 1H, Ar-H); 7.35-7.42 (m, 2H, Ar-H); 4.87 (s, 2H,CH2); 2.25 (s, 3H, CH3) 1.28 (s, 6H, CH3).

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; SIMBERG, Dmitri; SMITH, Weston J.; (107 pag.)WO2019/126565; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)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. Quality Control of 2-(Hydroxymethyl)isoindoline-1,3-dione

6.1 5-Phthalimidomethyl-2,3,3-trimethylindolenine To a stirred solution of 2,3,3,-trimethylindolenine (20 g, 126 mmol) in concentrated sulphuric acid (100 ml) at ambient temperature was added portionwise N-hydroxymethylphthalimide (20 g, 114 mmol). After 70 hours the reaction mixture was poured onto ice and made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered and dried. The product was obtained as a yellow solid (34.84 g, 87%).

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

Reference:
Patent; Carnegie Mellon University; US6686145; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 118-29-6,Some common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, molecular formula is C9H7NO3, 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.

Powdered N-hydroxymethylphthalimide (70 g, 0.4 mol) was added in small portion over a period of 45 min. to a stirred solution of 2,3,3-trimethyl-(3H)-indolenine (I), (70 g, 0.44 mol) in concentrated sulfuric acid (360 mL) at room temperature. The solution was stirred for 70 h at room temperature before being poured onto ice-water. Basification of the solution with conc. ammonium hydroxide gave a yellow powder which was filtered and dried. (111 g, yield 80%, m.p. 180-182 C.). 1 H NMR (DMSO d6), delta, 7.8-7.95 (m, 4H, phthalimido), 7.4 (s, 1 H, 4-H), 7.38 (d, 1 H, J=9.0 Hz, 6-H), 7.2 (d, 1 H, J=9 Hz, 7-H), 4.7 (s, 2 H, –CH2), 2.2 (s, 3 H, CH3), 1.2 (s, 6 H –(CH3)2).

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

Reference:
Patent; Carnegie Mellon University; US6008373; (1999); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-(Hydroxymethyl)isoindoline-1,3-dione

6.1 5-Phthalimidomethyl-2,3,3-trimethylindolenine To a stirred solution of 2,3,3,-trimethylindolenine (20g, 126mmol) in concentrated sulphuric acid (100ml) at ambient temperature was added portionwise N-hydroxymethylphthalimide (20g, 114mmol). After 70 hours the reaction mixture was poured onto ice and made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered and dried. The product was obtained as a yellow solid (34.84g, 87%).

According to the analysis of related databases, 118-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CARNEGIE MELLON UNIVERSITY; EP1042407; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 118-29-6, 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. 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 2,3,3-Trimethylindolenine (1) (2.0 g, 12.5 mmol, 1.1 eq.) and A (Hydroxymethyl)phthalimide (3) (2.02 g 11.4 mmol, 1 eq.) were added 14.7 mL of concentrated sulfuric acid and the system stirred at room temperature for 6 days. The reaction was then poured over ice and made basic with concentrated aqueous ammonium hydroxide. After crystallizing at -20 C overnight, the resulting precipitate was filtered, rinsed with ice cold water, and dried under vacuum to give indolenine 4 as a light yellow shiny crystalline solid. Yield 88.3%. XH NMR (400 MHz, CDCl3); d 7.82-7.87 (m, 2H, Ar- H); 7.67-7.72 (m, 2H, Ar-H); 7.44-7.48 (m, 1H, Ar-H); 7.35-7.42 (m, 2H, Ar-H); 4.87 (s, 2H,CH2); 2.25 (s, 3H, CH3) 1.28 (s, 6H, CH3).

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; SIMBERG, Dmitri; SMITH, Weston J.; (107 pag.)WO2019/126565; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 118-29-6 as follows. 118-29-6

200 mL of sulfuric acid were cooled to 0 0C. 48 g of 2,3,3 – trimethylindolenine were added to the sulfuric acid followed by the addition of 54 g of N-hydroxymethyl-phthalimide. The reaction mixture was stirred at room temperature for 7 days. The reaction mixture then was added to 500 g of crushed ice in a 2000-mL conical flask immersed in ice-salt bath. A solution of about 225 g of sodium hydroxide in 500 mL of water was cooled to 10 0C and then added dropwise to the magnetically stirred mixture in the conical flask. A white precipitate starts to form after addition of about half of the solution of sodium hydroxide. Addition of the sodium hydroxide is continued until the pH of the reaction mixture is strongly basic (pH > 12). The white solid is then filtered, washed with water (3×100 mL) and air- dried on a Buchner funnel for about 1 hour. The solid is then transferred to a 1000- mL one -neck round bottom flask, 300 mL of acetone is added and the mixture is stirred under reflux for 30 min. The flask is then cooled to 10 0C and the white product is filtered with suction on a Buchner funnel, washed with acetone (1 x50 mL), and air dried.The yield of the pure product is 70-75% (67-7O g). NMR: (DMSO-d6, 300 MHz) delta 1.33 (s, 6H, 2xCH3), 2.31 (s, 3H, CH3), 4.91 (s, 2H, CH2), 7.32 (dd, 3JH-H =8.7 Hz, 5Jn-H – 1.2 Hz, IH), 7.48 (dd, 5JH-H = 8.7 Hz, IH), 7.51 (dd, 5JH-H = 1.2 Hz, IH, 7.9-8.1 (m, 4H).; 6.1 2-(2, 3, 3-Trimethyl-3H-indol-5-ylmethyl)-isoindole-l, 3-dione, 1Sulfuric acid (420.0 mL, 7.879 mol; Sigma-Aldrich) was placed to the 1 L one -neck, round-bottom flask equipped with magnetic stirrer. The flask was cooled in ice-water bath and 2,3,3-trimethyl-3H-Indole, (100.0 g, 0.6280 mol; Sigma-Aldrich) was added to the sulfuric acid by drops during 45 min with stirring. The reaction mixture becomes a very viscous upon addition of 2,3,3-trimethyl-3H-indole, so stirring plate with adequate power and large magnetic stir bar is required. When addition of 2,3,3-trimethyl-3H-Indole was completed the ice bath was removed and 2- (hydroxymethyl)-lH-Isoindole-l,3(2H)-dione, (112 g, 0.632 mol; Aldrich) was added to the reaction mixture at once. The flask was closed with a glass stopper and the stirring was continued for 168 hours at room temperature. In about 12 hours all solid, 2-(hydroxymethyl)-lH-Isoindole-l,3(2H)-dione dissolved and clear brown solution formed.After 168 hours the content of the flask was poured into 4-L conical flask containing 1 kg of ice. The 4-L flask was immersed in ice-salt bath, equipped with mechanical stirrer. A cooled to 10 0C solution of 550g of NaOH in 1.5 L of water was slowly added to the reaction mixture at such rate that temperature inside of flask didn’t increase higher than 20 0C. The addition takes about 1 hour. The white precipitate formed was filtered on Buchner funnel with suction and dried on air for 12 hours.The crude 2-(2,3,3-Trimethyl-3H-indol-5-ylmethyl)-isoindole-l,3-dione was placed in conical 2 L flask, 1 L of acetone was added and the mixture was magnetically stirred with heating until acetone start to boil. The heating was reduced to maintain a very gentle boiling and the content of the flask was stirred for additional 10 min. Flask was cooled using ice-water bath and the separated crystals were filtered, washed with acetone and dried. The yield of the first crop with m.p. = 186-187 0C was 82 g. The mother liquor was reduced in volume to about 300 mL and cooled at -10 0C overnight. The separated crystals were filtered, washed with acetone and dried. The yield of the second crop with m.p. = 184-185 0C was 45 g. The total yield was 126 g (63% of theoretical).Analytical Results for 1:M.p. = 186-187 0C1H NMR (CDCl3, 300 MHz) delta 1.28 (s, 6H), 2.25 (s, 3H), 4.87 (s, 2H), 7.38- 7.45 (m, 3H), 7.68-7.71 (m, 2H), 7.83-7.86 (m, 2H). 13C NMR (CDCl3, 75 MHz) delta 15.4, 23.0, 41.7, 53.7, 119.8, 122.0, 123.3, 128.4,132.2, 133.3, 133.9, 146.1, 153.5, 168.0, 188.5.

According to the analysis of related databases, 118-29-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; WO2008/157762; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, molecular formula is C9H7NO3, 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. 118-29-6.

A mixture of phthalimide (41.14 g, 0.30 mol) and distilled water (100 mL) was stirred for 10 min at room temperature. After addition of formaldehyde solution (40%, 27 mL, 0.36 mol), the resulting solution was refluxed for 1.5 h. After cooling to 0-5 C, the resulting precipitate was collected by filtration, washed with cold water (0-5 C, 200 mL) and dried in air to give the corresponding N-hydroxymethylphthalimide (51.01 g, 96% yield).(0010)A solution of thionyl chloride (23.0 mL, 37.7 g, 0.32 mol) in dichloromethane (50 mL) was slowly added to a mixture of the resulting N-hydroxymethylphthalimide and dichloromethane (550 mL) and N,N-dimethylformamide (350 mL) during 30 min at room temperature with stirring. The resulting mixture was further stirred for 2 h at room temperature. After cooling to 0 C, water (200 mL) was added slowly. And the solution was neutralized to pH 6.7-7.0 by using saturated aqueous NaHCO3 solution. The organic layer was separated and then was dried over anhydrous magnesium sulfate. After evaporation of the solvent under the reduced pressure, the residue was washed with n-hexane (100 mL) to give N-chloromethylphthalimide (51.4 g, 93% yield).(0011) N-Chloromethylphthalimide (51.0 g, 0.26 mol) was dissolved in acetone (500 mL) and potassium O-ethyl xanthate (43.9 g, 274 mmol) was added portionwise in an ice water bath under stirring. The resulting solution was further stirred for 10 h at room temperature. After removal of the solvent, the residue was dissolved in dichloromethane. The resulting solution was washed with water and dried over sodium sulfate. After removal of the solvent under the reduced pressure, pale yellow solid was obtained and recrystallized from ethyl acetate to afford the xanthate 1 as colorless crystals 67.2 g, 92% yield, mp: 99-100 C. Lit.20 mp: 94-95 C. 1H NMR (CDCl3, 400 MHz) (delta, ppm) 1.47 (t, J=7.1 Hz, 3H, CH3), 4.68 (q, J=7.1 Hz, 2H, CH2), 5.34 (s, 2H, CH2), 7.75 (dd, J=5.5, 3.1 Hz, 2H, ArH), 7.88 (dd, J=5.5, 3.1 Hz, 2H, ArH). 13C NMR (CDCl3, 100 MHz) (delta, ppm) 13.7, 41.2, 70.5, 123.6, 131.8, 134.4, 166.6, 210.2.

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

Reference:
Article; Huang, Zhongyan; Xu, Jiaxi; Tetrahedron; vol. 69; 3; (2013); p. 1050 – 1056;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118-29-6, 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 118-29-6 as follows.

To a stirred solution of 2,3,3,-trimethylindolenine (20 g, 126 mmol) in concentrated sulphuric acid (100 ml) at ambient temperature was added portionwise N-hydroxymethylphthalimide (20 g, 114 mmol). After 70 hours the reaction mixture was poured onto ice and made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered and dried. The product was obtained as a yellow solid (34.84 g, 87%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 118-29-6, and friends who are interested can also refer to it.

Reference:
Patent; Carnegie Mellon University; US2003/224391; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem