Author: tianli

Some common heterocyclic compound, 496-15-1, name is Indoline, molecular formula is C8H9N, 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. 496-15-1

COMPARATIVE EXAMPLE 1 1,3-Dihydro-1,3,3-trimethyl-6′-(2,3-dihydroindol-1-yl) spiro[2H-indole-2,3′-3H-naphtho[2,1-b][1,4]oxazine] A mixture of 1-nitroso-2-naphthol (17.3 g; 0.10 mol) and indoline (23.8 g; 0.20 mol) in trichloroethylene (150 ml) was heated under reflux for 10 min. A solution of 1,3-dihydro-1,3,3-trimethyl-2-methyleneindoline (17.3 g; 0.1 mol) in trichloroethylene (100 ml) was added in one batch and the resulting mixture heated under reflux for 1 h. The solution was evaporatedand the oily residue treated with acetone to yield 1,3-Dihydro-1,3,3-trimethyl-6′-(2,3-dihydroindol-1-yl)spiro [2H-indole-2,3′-3H-naphtho[2,1-b][1,4]oxazine] as a yellow solid (4.44 g; 10%). m.p 255-7 C. STR10

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 496-15-1, its application will become more common.

Reference:
Patent; Pilkington plc; US5446151; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

71294-03-6, A common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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 stirred slurry of potassium tert-butoxide (185 g, 1.65 mol) in tthetatrahydrofuran (1350 mL) was added 7-fluoro-oxindole (50 g, 0.33 mol) and copper (I) bromide-dimethyl sulfide complex (7 g, 0.033 mol). Methyl iodide (150 g, 1.06 mol.) was added to the mixture at 5-100C. The reaction mixture was stirred at 20- 25C for 1 hour. 10% NH4CI (1000 mL) was added to the reaction mixture. The two layers were separated. The organic layer was concentrated via vacuum distillation at 25-400C to reach a volume of 250 mL. The aqueous layer is extracted with tert- butyl methyl ether (2 x 500 mL). The concentrated organic layer and tert-butyl methyl ether extraction layers were combined and washed with 15% NaCI (250 mL). The organic solution was filtered through silica gel (100 g). Heptane (1250 mL) was added to the filtrate. The mixture was concentrated under atmosphere at 60-950C to reach a volume of 700 mL. The concentrate was cooled to 0-50C from 85-95C over 2 hours to crystallize. Solid was filtered, washed with heptane (100 mL), and oven- dried to give 41 g (69.4%) of a beige solid 7-fluoro-3, 3-dimethyl-oxindole, 92% w/w purity by HPLC.

The synthetic route of 71294-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2008/24492; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, Adding some certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, 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 2058-72-2.

General procedure: A solution of carbonyl compounds 1 (0.30 mmol), isatins 2 (0.40 mmol) and 50 mol% Cat. Et2NH (0.15 mmol) in EtOH (2.0 mL) was stirred at 40 oC for 15 h. After completion of the reaction, as indicated by TLC, the removal of solvent and purification by flash column chromatography (hexane/EtOAc= 5:1~3:1) were carried out to furnish the corresponding products 3.

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 2058-72-2.

Reference:
Article; Lin, Bing; Lu, Yi; Huang, Jun-Fei; Gong, Yi; Liu, Huan-Huan; Liu, Xiong-Li; Tian, Min-Yi; Zhou, Ying; Yuan, Wei-Cheng; Synthetic Communications; vol. 47; 6; (2017); p. 609 – 617;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

99365-40-9, The chemical industry reduces the impact on the environment during synthesis 99365-40-9, name is 6-Bromoindolin-2-one, I believe this compound will play a more active role in future production and life.

6-bromoindolin-2-one (0.424 g; 2 mmol), potassium acetate (0.687 g; 7.0 mmol) and bis[pinacolato]diborane (0.762 g; 3.0 mmol) were placed in a 20 mL microwave vial, dissolved in dry DMF (13 mL) and the flask was purged with nitrogen. The catalyst [1 ,1 ‘- Bis(diphenylphosphino)ferrocene]palladium(ll) chloride, complex with dichloromethane (0.169 g; 0.20 mmol) was added, the flask was again purged with argon, sealed and the reaction was heated at 950C for 18 h. The reaction mixture was diluted with water and the suspension was extracted twice with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (10 – 80 %) in heptane furnished 0.390 g (40 %) of the title compound.ESI/APCI(+): 260 (M+H);1H NMR (DMSO-d6) delta 10.40 (s, 1 H), 7.27 (dd, J= 7,3, 0,8 Hz, 1 H), 7.21 (m, 1 H), 7.07 (s, 1 H), 3.50 (s, 2 H), 1.28 (s, 12 H).

The chemical industry reduces the impact on the environment during synthesis 6-Bromoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; CHALTIN, Patrick; DEBYSER, Zeger; DE MAEYER, Marc; MARCHAND, Arnaud; MARCHAND, Damien; SMETS, Wim; VOET, Arnout; CHRIST, Frauke; WO2011/15641; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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.

General procedure: Acetone (150mL) and dibromoalkyl (30mol) were added to a 250mL three-necked round-bottom flask fitted with a mechanical stirrer and reflux condenser. Potassium phthalimide (11.85g, 10 mol) was added slowly over a 15-min period, and then the reaction mixture was heated under reflux for 10h. The reaction mixture was filtered via suction, and the acetone was removed via rotary evaporation. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:14) to afford 2-5 as white solid.

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 1074-82-4.

Reference:
Article; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

Example 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104618-32-8, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding some certain compound to certain chemical reactions, such as: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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 14192-26-8. 14192-26-8

A mixture of methyl oxindole-6-carboxylate (11.47 g) and acetanhydride (32 ml) was stirredat the bath temperature of 138C; a clear red solution was produced within 10 mm. Thereaction mixture was stirred at 138C for 6 h, then left to stand at 20C for 4 h and the crystallization of the product was completed in 2 h at 10C. The product was filtered off, washed with petroleum ether and finally with glacial methanol. The yield was 12.15 g (87%) of reddish crystals

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 Methyl 2-oxoindoline-6-carboxylate.

Reference:
Patent; ZENTIVA, K.S.; MECA, Ludek; (16 pag.)WO2017/16530; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life. 2058-72-2

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

The chemical industry reduces the impact on the environment during synthesis 2058-72-2. I believe this compound will play a more active role in future production and life.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

324-03-8, Name is 6-Fluoroindoline-2,3-dione, 324-03-8, 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.

General procedure: Isatin derivatives (S1) were synthesized by treating isatins with NaH and then reacting with methyl iodide or benzyl bromide or allyl bromide, respectively, in dry DMF at room temperature.

Statistics shows that 6-Fluoroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 324-03-8.

Reference:
Article; Zhang, Lin-Lin; Da, Bing-Chao; Xiang, Shao-Hua; Zhu, Shuai; Yuan, Zi-Yun; Guo, Zhen; Tan, Bin; Tetrahedron; vol. 75; 12; (2019); p. 1689 – 1696;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

4403-36-5, 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. 4403-36-5 name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, 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.

A solution of p-bromophenethyl bromide (86.87 g, 0.33 mol),Thiourea (30.14 g, 0.396 mol),Anhydrous ethanol (120 ml) was placed in a round bottom flask,Mixed heating reflux,Until there is white precipitation,After filtration,Placed in a single mouth bottle by adding NaOH (135ml, 5M) aqueous solution,Reflow heating for five hours,After dilute hydrochloric acid is acidified,Separating the thiol layer,Dried over anhydrous sodium sulfate,20cm flavor fraction distillation column distillation (distillation range 146-148 ).Bromophenethyl bromide can be obtained by passing 2- (4′-bromophenyl) ethanol to hydrogen bromide.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Institute of Printing; Wang, Wenguang; Yang, Mingcong; Pu, Jialing; (29 pag.)CN104961665; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem