Category: 7147-90-2

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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 7147-90-2

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added methylmagnesium chloride (3 M in THF, 20 mL) dropwise at 0 C. After the addition, the mixture was stirred at 0 C for 3 hours before it was quenched with satd. aq. NH4CI solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regioisomers (3.95 g, 100%). MS: 198.1 (M+H+).; Under N2 protection, triethylsilane (23 g, 200 mmol) and trifluoroboron etherate (8.51 g, 60 mmol) were added successively at -15 C to a mixture of 5-chloro-3-hydroxy-3-methyl- 2,3-dihydro-isoindol- 1 -one and 6-chloro-3-hydroxy-3-methyl-2,3-dihydro-isoindol- 1 -one (3.95 g, 20 mmol) in dry DCM (100 mL). Afterwards, the reaction mixture was stirred at room temperature for 2 hours and a saturated aqueous solution of NaHC03 (30 mL) was added. The mixture was then extracted with DCM and the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude mixture of products. The two regioisomers were separated by prep-HPLC to give the title compounds, 5-chloro-3-methyl-2,3-dihydro-isoindol-l-one (0.4 g, 11%) and 6-chloro-3- methyl-2,3-dihydro-isoindol-l-one (0.35 g, 9.6%) as white solids. MS: 182.0 (M+H+).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; 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; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-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. COA of Formula: C8H4ClNO2

General procedure: (0.107) Intermediate 4 (0.001 mol) was dissolved in 15 ml of N ‘N-dimethylformamide solution, anhydrous potassium carbonate (0.00 mol) was added, methyl iodide (0.0015 mol) or benzyl chloride (0.0015 mol)The mixture was stirred at room temperature for 5 hours. The filtrate was distilled off and the solvent was distilled off, and the residue was recrystallized from methanol to give the intermediate compound 17. 17a: pale yellow solid, yield 72.4%

The synthetic route of 5-Chloroisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Synthetic Route of 7147-90-2, 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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added benzylmagnesium chloride (2 M in THF, 30 mL) dropwise at 0 C. After the addition, the reaction mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regio isomers (5.47 g, 100%). MS: 274.1 (M+H+).

The chemical industry reduces the impact on the environment during synthesis 5-Chloroisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; 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; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5-Chloroisoindoline-1,3-dione

7a: A mixture of concentrated sulfuric acid (24 mL) and fuming nitric acid (1.5 mL) was added dropwise to 4-chloro-phthalimide 6 (4.90 g, 27.0 mmol). The reaction mixture was heated at 80 C for 0.5 h. After cooling to r.t. the dark red solution was poured into ice. The resulted yellow precipitate was collected by filtration, washed with water, dried in vacuum affording a pale yellow solid 7a (3.52 g, 58% yield). 1H NMR (DMSO-d6): delta (ppm) 11.87 (s, 1H, CONHCO), 8.51 (s, 1H, Ar-H), 8.27 (s, 1H, Ar-H). 13C NMR (DMSO-d6): delta (ppm) 166.66, 166.62, 151.28, 135.96, 132.43, 130.30, 126.03, 119.62.

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Xiaoyu; Zhao, Jing; Zhang, Wandong; Chen, Long; Chinese Chemical Letters; (2018); p. 331 – 335;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-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 7147-90-2, SDS of cas: 7147-90-2

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added benzylmagnesium chloride (2 M in THF, 30 mL) dropwise at 0 C. After the addition, the reaction mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regio isomers (5.47 g, 100%). MS: 274.1 (M+H+).; Under N2 protection, triethylsilane (23 g, 200 mmol) and TFA (10 mL) were added successively to a mixture of 3-benzyl-5-chloro-3-hydroxy-2,3-dihydro-isoindol-l-one and 3-benzyl-6-chloro-3-hydroxy-2,3-dihydro-isoindol-l-one (5.47 g, 20 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. NaHC03 solution (30 mL) and extracted with DCM (2 x 30 mL). The combined organic layers were washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude mixture of products. The desired regioisomer, 3-benzyl-5-chloro-2,3-dihydro-isoindol- 1 -one was obtained by prep- HPLC separation as a white solid (1.03 g, 20%). MS: 258.1 (M+H+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; 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; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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. Safety of 5-Chloroisoindoline-1,3-dione

General procedure: (0.107) Intermediate 4 (0.001 mol) was dissolved in 15 ml of N ‘N-dimethylformamide solution, anhydrous potassium carbonate (0.00 mol) was added, methyl iodide (0.0015 mol) or benzyl chloride (0.0015 mol)The mixture was stirred at room temperature for 5 hours. The filtrate was distilled off and the solvent was distilled off, and the residue was recrystallized from methanol to give the intermediate compound 17. 17a: near white solid, yield 53.1%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7147-90-2, its application will become more common.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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.

30 g (165.2 mmol) of 5-chloroisoindolin-1,3-dione, sodium tertbutoxide 198.2 mmol, methyl iodide 198.2 mmolAnd 200 mL of toluene were mixed, refluxed, heated for 30 minutes, and 1.6 mmol of tetrakistriphenylphosphinepalladium was added thereto, followed by stirring for 3 hours in a reflux state. After the reaction, the reaction solution was returned to room temperature, extracted with water, and the organic layer was recrystallized twice from chloroform and hexane to give 23.9 g of Compound 1-G (yield 74%).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; SUNGKYUNKWAN University Research & Business Foundation; Yoon Hong-sik; Hong Wan-pyo; Kang Yu-jin; Kim Jin-ju; Han Si-hyeon; (93 pag.)KR2019/101894; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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.

4-Chlorophthalimide (273 mg) is dissolved in a minimum of boiling ethanol (ca. 2.5 ml). 37% formaldehyde solution (0.15 ml) is added to the still hot solution followed by N-(4-chlorophenyl)glycine (279 mg). Reflux is continued for 3 h. The yellow solution is kept in the refrigerator overnight. The yellow precipitate is collected by suction filtration, washed with ethanol, and dried in vacuo. The crude is recrystallised from ethanol to provide N-[(5-chloro-1,3-dioxo-2-isondolinyl)methyl]-N-(4-chlorophenyl)glycine (135 mg) as light yellow crystals. 1H-NMR (500 MHz, DMSO-d6): delta (ppm)=4.26 (s, 2H), 5.24 (s, 2H), 6.97 (d, J=9.1 Hz, 2H), 7.22 (d, J=9.1 Hz, 2H), 7.90 (d, J=1.2 Hz, 2H), 7.97 (t, J=1.2 Hz, 1H), 12.71 (br s, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=51.77 (CH2), 54.72 (CH2), 114.39 (2CH), 121.70 (C), 123.35 (CH), 124.99 (CH), 128.39 (2CH), 129.97 (C), 133.41 (C), 134.38 (CH), 139.41 (C), 145.34 (C), 167.01 (CO), 167.35 (CO), 171.48 (CO).MS (+ESI): m/z=379 (M+H).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2, A common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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 intermediate compound 4 (0.05 mol) was slowly added to 30 ml of 0 C concentrated H2SO4,Control the temperature does not exceed 12 C; added, ice bath conditions slowly add mixed acid (fuming nitric acid / concentrated sulfuric acid = 1/1) 15ml, remove the ice bath, 55 C heating and stirring for 12 hours. The reaction solution was poured into 3 times of ice water, and the mixture was stirred while stirring, and the solid was filtered. The filter cake was washed three times with 100 ml of water and recrystallized from 95% ethanol to give intermediate 11 as a pale yellow solid in 16%

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem