Category: 15362-40-0

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15362-40-0 name is 1-(2,6-Dichlorophenyl)-2-indolinone, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 15362-40-0

Pyrrole-2-carboxaldehyde (1 mmol) and 4-fluorobenzyl bromide (1.5 mmol) were reacted in the presence of NaH (1.5 mmol) in DMF (solvent) at 0 – 25 C for 30 min. The progress of the reaction was monitored with TLC. After completion, the reaction was quenched by the addition of water and the crude product was isolated by extraction with ethyl acetate (2 x 50 ml). The organic layers were combined, dried over Na2SO4 and distilled in vacuum to give N-(4-flurobenzyl)pyrrole-2-carboxaldehyde (A) which was purified by column chromatography using ethyl acetate: hexane (1:50). A (1 mmol) was reacted with 1-(2,6-dichlorophenyl)-2-indolinone (1.2 mmol) in the presence of piperidine (0.2 mmol) in CHCl3/ DMF under microwave irradiations at 100 C for 1h. The progress of the reaction was monitored with TLC, after completion reaction was worked up by adding water and extraction with chloroform (2 x 50 ml). Combined organic layers were dried over Na2SO4 and distilled in vacuum to give crude product 3b which was purified by column chromatography using ethyl acetate: hexane (3:50) as eluent. Yellow Solid, yield 75 %, mp 130-132 C; IR (KBr): 3077, 2929, 1702, 1600, 1509, 1396; 1H NMR (500 MHz, CDCl3) delta: 1H NMR (500 MHz, CDCl3, 25 C, TMS) delta: 5.38 (s, 2H, CH2), 6.41-6.43 (m, 2H, ArH), 7.05-7.10 (m, 4H, ArH), 7.13-7.16 (m, 3H, ArH), 7.31 (d, 1H, J = 7.55 Hz, ArH), 7.38 (t, 1H, J = 7.95 Hz, ArH), 7.42 (s, 1H, =CH), 7.53 (d, 2H, J = 8.08 Hz, ArH), 8.48 (dd, 1H, J = 3.45 Hz, 1.29 Hz, ArH); 13C NMR (125 MHz, CDCl3, normal/DEPT-135) delta: 50.6 (-ve, CH2), 108.7 (+ve, CH), 110.9, (+ve, CH), 116.0 (+ve, CH), 116.1 (+ve, CH), 117.3 (+ve, CH), 117.7 (+ve, CH), 122.0 (+ve, CH), 122.2 (+ve, CH), 122.6 (+ve, CH), 125.1 (ArC), 127.3 (+ve, CH), 127.9 (+ve, CH), 128.0 (+ve, CH), 128.5 (ArC), 128.8 (+ve, CH), 129.0 (+ve, CH), 130.4 (+ve, CH), 131.1 (ArC), 133.1 (ArC), 135.9 (ArC), 139.3 (ArC), 161.3-161.4 (J = 247 Hz, CF), 164.8 (C=O); HRMS (ESI) m/z for C26H17Cl2FN2O [M+H]+ calcd. 463.0774, found 463.0734.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2,6-Dichlorophenyl)-2-indolinone, and friends who are interested can also refer to it.

Reference:
Article; Kaur, Jagroop; Kaur, Baljit; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 28; 2; (2018); p. 129 – 133;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 15362-40-0.

Reference:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

15362-40-0, 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 15362-40-0 as follows.

To the four-necked flask was added 668 ml of water and then compound IV (233 g, 0.84 mol), potassium hydroxide (94.3 g,1.68 mol) and the temperature was raised to 100 C for 5 hours. Cool to 60 ~ 65 C, vacuum filter, add a small amount of water, filter cake at 85 CAfter dissolving in water,Join eta SO4 (27 0 g, 1.6 8mo 1) aqueous solution at 8 5 C for 1 hour, cooled and filtered to give a white solid494.0 g (Compound I: diclofenac zinc) in a yield of 90%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 15362-40-0, and friends who are interested can also refer to it.

Reference:
Patent; Jilin University; Liaoyuan Yinying Pharmaceutical Co., Ltd.; Li Guiying; Wang Zhaokun; Li Shumei; Peng Xiaojuan; Jin Xingtong; (8 pag.)CN106905178; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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. 15362-40-0

A finely ground mixture of chromone-3-carboxaldehyde(1 mmol) and oxindole/indolinone (1-(2,6-dichlorophenyl)-2-indolinone)/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1.2 mmol) was irradiated in microwave oven for 1 min and completion of the reaction was monitored with TLC. Reaction mixture was washed with diethyl ether to get pure compounds 5-10.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15362-40-0, its application will become more common.

Reference:
Article; Shaveta; Singh, Amrinder; Kaur, Matinder; Sharma, Surbhi; Bhatti, Rajbir; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 185 – 192;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

General procedure: A finely ground mixture of 5-substituted indole-3-carboxaldehyde (1 mmol) and active methylene compound (indolinone/oxindole/barbituric acid/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one)/2-trifluoromethylbenzaldehyde (1.2 mmol) was irradiated in microwave oven for 1-5 min. The solid product was washed with diethyl ether and purified by column chromatography to get pure products 2-5 and 11-28 except compound 3. Compound 3 was prepared by treatment of 5-substituted indole-3-carboxaldehyde with indolinone in ethanol-water in presence of NaOH (1.5 mmol).

Statistics shows that 15362-40-0 is playing an increasingly important role. we look forward to future research findings about 1-(2,6-Dichlorophenyl)-2-indolinone.

Reference:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. 15362-40-0

To the four-necked flask was added 668 ml of water and then compound IV (233 g, 0.84 mol), potassium hydroxide (94.3 g,1.68 mol), heated to 100 C for 5 hours, cooled to 60 C to 65 C,Vacuum filter, add a small amount of water, filter cake at 85 CAfter dissolution in water, zinc chloride (229 g, 1.68 mol 1) in water was added, reacted at 85 C for 1 hour,Cooling, filtration was white solid 488.5g (compound I: diclofenac zinc), the yield of 89%

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 15362-40-0.

Reference:
Patent; Jilin University; Liaoyuan Yinying Pharmaceutical Co., Ltd.; Li Guiying; Wang Zhaokun; Li Shumei; Peng Xiaojuan; Jin Xingtong; (8 pag.)CN106905178; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem