Author: Jessica.F

Reference of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.

General procedure: An equivalent mixture of aldehyde (1 mmol) and active methylene compound- barbituric acid/1, 3-dimethyl barbituric acid/ 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1 mmol) in dimethyl formamide (2 mL) was subjected to microwave irradiations at 150 C for 1 h. The reaction was monitored by TLC. After the completion, the reaction was quenched by adding water to the reaction mixture. The crude product was separated out as solid, which was further purified by washing with ethanol, hot water and recrystallization from chloroform:methanol (9:1).

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Singh, Harpreet; Kaur, Manpreet; Kaur, Harpreet; Sharma, Indu; Bhandari, Anmol; Kaur, Gurcharan; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
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Application of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

The chemical industry reduces the impact on the environment during synthesis 7-Chloroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
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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;,
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Adding a certain compound to certain chemical reactions, such as: 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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 15362-40-0, Recommanded Product: 1-(2,6-Dichlorophenyl)-2-indolinone

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).

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:
Article; Shaveta; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 440 – 450;,
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56341-37-8, name is 6-Chlorooxindole, 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. Product Details of 56341-37-8

General procedure: Synthesis of 6-chlorooxindole derivatives was carried out by refluxing 6-chlorooxindole with different aromatic aldehydes in ethanol in the presence of a catalytic amount of piperidine. The reaction mixture was refluxed for 3 h. After completion of reactionas determined by TLC analysis, the contents were cooled and concentrated at reduced pressure to afford solid 3-oxindole derivatives. The product was washed with equal volumes of a mixture of hexane-ethyl acetate (25 mL) and dried to afford compounds 1-25.20 1H NMR, EI spectroscopy and CHN analysis were used for the determination of their structures. 4.1.18 (E)-3-(3-Methoxybenzylidene)-6-chloroindolin-2-one (18) Yield: 0.24 g (84%); 1H NMR (500 MHz, DMSO-d6): delta 10.75 (s, 1H, -NH), 7.63 (s, 1H, =CH), 7.52 (d, 1H, J4,5 = 8.0 Hz, H-4), 7.43 (t, 1H, J5′(4′,6′) = 8.0, H-5′), 7.24(t, 1H, J4′(3′,5′) = 8.0, H-4′), 7.23 (d, 1H, J6′,5′ = 8.0 Hz, H-6′), 7.04 (d, 1H, J3′,4′ = 8.0 Hz, H-3′), 6.93 (dd, 1H, J5,7 = 1.5, J5,4 = 8.0 Hz, H-5), 6.88 (d, 1H, J7,5 = 1.5 Hz, H-7), 3.79 (s, 3H, -OMe); MS: m/z (rel. abund.%) 285 (M+, 100), 178 (59), 152 (32), 63 (56); Anal. Calcd for C16H12ClNO2 (285.72): C, 67.26; H, 4.23; Cl, 12.41; N, 4.90; O, 11.20; Found: C, 67.28; H, 4.22; N, 4.88.

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khan, Momin; Yousaf, Muhammad; Wadood, Abdul; Junaid, Muhammad; Ashraf, Muhammad; Alam, Umber; Ali, Muhammad; Arshad, Muhammad; Hussain, Zahid; Khan, Khalid Mohammed; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3441 – 3448;,
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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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Nitroindoline

Step A-Preparation of 1-(1-methyl(4-piperidyl))-6-nitroindoline 6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane, N-methyl-4-piperidone (5 g) was added to the mixture, followed by 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) was added to the reaction mixture and stirred for 1 h.The resulting mixture was separated by separation funnel, the organic layer was extracted once with saturated NaHCO3 solution and once with brine.The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford an orange oil. MS: 262 (M+1). Calc’d. for C14H19N3O2-261.32.

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-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 6941-75-9, Recommanded Product: 6941-75-9

Sodium borohydride (12.6 g, 330 mmol) was added to a mixed solvent of ethanol (300 mL) and water (50 mL)Add 5-bromophthalimide in 4 batches with stirring at 20-30 C(30.0 g, 132 mmol, stirred for 30 min after each addition).After the addition was complete, the reaction was incubated for 2h, hydrochloric acid solution (mass percent concentration 18%, 180g, 883.5mmol) was added dropwise at 20-30 C, heated to 75-85 C after dropping,The reaction was incubated 3h, evaporated to ethanol under reduced pressure to give an aqueous white solid.Solid plus toluene (225ml), water (300ml), 45-55 C for 30min, to clarify the upper and lower.The layers were separated and the aqueous layer was extracted with toluene (150 mL * 1).The combined toluene layers were washed with saturated brine (150 ml * 1).Divided toluene layer, add water 225ml, sodium hydroxide (6g), stirred at 80 for 3h. The hot toluene is removed by hot section and extracted with toluene (50 ml * 1).Sub-water layer was cooled to 30 C dropwise hydrochloric acid (21.0g), heated to 75-85 C, incubated for 2-3h.Drop to 50 C and extract with toluene (225 ml * 1, 150 ml * 1).Toluene was combined and washed with water (50 ml * 1).Atmospheric pressure concentrated toluene layer to 5.5X, slowly cooled to 50 precipitated white crystals, 50 stirring 1h, then slowly cooled to 0-5 incubated 1h.Filtration and crystallization from ice-toluene (60 ml) gave a white 5-bromophthalide (13.7 g, 48.5% yield) after drying in vacuo. HPLC: 98.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Shanghai He Quan Pharmaceutical Research And Development Co., Ltd.; Shanghai He Quan Pharmaceutical Co., Ltd.; Changzhou Hequan Pharmaceutical Co., Ltd.; Changzhou Hequan Drug Discovery Co., Ltd.; Guo Wei; Zhang Qing; Li Yongkai; Luo Qiyu; Xie Chengfu; Shi Feng; Fu Xiaoyong; Chen Minzhang; (7 pag.)CN107082769; (2017); A;,
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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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H9NO3

To the solution of compound A19 (500 mg, 2.46 mmol) in DMF (5 mL) was added NaN3 (319 mg, 4.92 mmol) and NH4Cl (158 mg, 2.95 mmol). The mixture was stirred at 80 C for 3 hours to give a yellow mixture. LCMS showed the reaction was completed. The mixture was partitioned between EtOAc (30 mL) and H20 (20 mL). The aqueous phase was extracted with EtOAc (30 mL x 2). The combined organic extract was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give compound A20 (820 mg, crude) as a yellow oil.

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QURIENT CO., LTD.; LEAD DISCOVERY CENTER GMBH; NAM, Kiyean; KIM, Jaeseung; JEON, Yeejin; YU, Donghoon; SEO, Mooyoung; PARK, Dongsik; EICKHOFF, Jan; ZISCHINSKY, Gunther; (217 pag.)WO2019/197549; (2019); A1;,
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Reference of 32372-82-0, These common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, 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.

To a solution of 2-chloropyridin-4-amine (0.5 g, 3.90 mmol) in toluene (12 ml) were added isoindoline hydrochloride (0.91 g, 5.85 mmol), BINAP (0.24 g, 0.39 mmol) and potassium tertbutoxide (2.07 g, 9.76 mmol) at rt. The mixture was degassed for 10 mm before addition of Pd2(dba)3 (0.178 g, 0.19 mmol). The reaction mixture was at 110C for 4 hrs. The resulting mixture was poured into cold water (200 ml) and combined with two other batches prepared by an identical method on the same scale. The resulting mixture was extracted with DCM (3 x 100 ml). The organic phase was collected, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (3% MeOH in DCM) yielding 2-(isoindolin-2-yl)pyridin-4- amine (1.2 g, 5.67 mmol). LCMS: Method C, 1.57 mi MS: ES+ 212.29.

The synthetic route of 32372-82-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; KEMP, Mark Ian; STOCKLEY, Martin Lee; MADIN, Andrew; (95 pag.)WO2017/103614; (2017); A1;,
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Electric Literature of 446292-08-6,Some common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, molecular formula is C22H19N3O6, 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.

(1) 40 g of the compound of Formula 4 and 200 mL of ethanol are mixed at room temperature.Stir at room temperature. The temperature was raised to 40 C., a 200 mL aqueous solution of 12.0 potassium sulfide was dropped at 60 C. or lower, and the reaction was carried out at 40 to 40 C. for 4 to 5 hours. After 50 C, vacuum concentration to 150 ~ 200mL, 0 ~ 10 C stirring for 2 hours,Filtration and drying gave 26.3 g of a dry product of the compound of formula 3 in a yield of 95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Zhejiang Mei Nuohua Pharmaceutical Chemical Co., Ltd.; Liu Xiong; Huang Xiangliang; Cao Qian; Chen Weiren; Yao Chengzhi; Zeng Wei; (9 pag.)CN107936006; (2018); A;,
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