Category: 147149-84-6

Electric Literature of 147149-84-6, A common heterocyclic compound, 147149-84-6, name is 4-Bromo-5-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.

Hydrogen peroxide (40 ml, 391.60 mmol) was added to a solution of 4-bromo-5-methyl-1H-indole-2,3-dione (20 g, 83.31 mmol) in 2M NaOH (400 ml) at rt. The resulting solution was stirred at rt for 2 h. Sodium sulfite (48 g) was then added and the mixture was stirred for another 0.5 h at rt. The reaction mixture was extracted with EtOAc (200 mL) and the aqueous layer pH adjusted to pH 4 with concentrated HCl. A precipitate was collected by filtration, washed with water (300 ml) and dried under vacuum to afford 6-amino-2-bromo-3-methylbenzoic acid (12.4 g, 65%) as a pale yellow solid; 1H NMR (400 MHz, MeOD, 30 C.) 2.29 (3H, s), 6.70 (1H, d), 7.07 (1H, d); m/z: ES+ [M+H]+=230.

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; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 147149-84-6, name is 4-Bromo-5-methylindoline-2,3-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 147149-84-6, Product Details of 147149-84-6

A mixture of 3N NaOH (80 ml, 79.15 mmol) and 4-bromo-5-methyl-lH-indole-2,3-dione (19 g, 79.15 mmol) was heated at 80C. To the solution was added hydrogen peroxide (18 ml, 176.22 mmol) slowly and the mixture was stirred for 1 hour and the mixture cooled to 5C then acidified to pH5 with concentrated HCI. The solution was evaporated to dryness and methanol (100 ml) then added. The mixture was filtered and the filtrate was evaporated to yield 6-amino-2-bromo-3-methylbenzoic acid (18 g, 99%) as brown solid. 1H NMR (400 MHz, DMSO, 30C) 2.21 (3H, s), 6.71 (1H, d), 7.07 (1H, d). Three exchangeable protons not observed m/z: ES+ [M+H]+ = 230.

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, 4-Bromo-5-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; KETTLE, Jason, Grant; BAGAL, Sharanjeet, Kaur; EATHERTON, Andrew, John; FILLERY, Shaun, Michael; ROBB, Graeme, Richard; LAMONT, Scott, Gibson; KEMMITT, Paul, David; GOLDBERG, Frederick, Woolf; (158 pag.)WO2019/215203; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 147149-84-6,Some common heterocyclic compound, 147149-84-6, name is 4-Bromo-5-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 microwave reaction tube were added indoles (2 mmol), isatins (1 mmol) and HFIP (2 mL). After sealing the tube, the mixture was heated to 75C in an oil bath and stirred for 1 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, and the resulting precipitate was then filtered, washed with ether, and dried to give compound 3a-3q and 4a-4j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-5-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Cheng, Jialing; Liu, Hong-Min; Wang, Shuai; Yu, Bin; Yuan, Xiaohan; Chinese Chemical Letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem