Tag: M.W=100-200

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

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

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

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

222036-66-0, 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. 222036-66-0, name is 5-Aminoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

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Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 2058-74-4, name is 1-Methylisatin, This compound has unique chemical properties. The synthetic route is as follows., 2058-74-4

General procedure: To a mixture of indole-2,3-dione 1a (1.0 mmol) and o-aminothiophenol 2 (1.0 mmol) in distilled water (5.0 mL), was added TBAB (0.0483 g, 15 mol %). This reaction mixture was allowed to stir magnetically at 60 C. Progress of the reaction was monitored by TLC (Pet. ether-ethyl acetate = 4:1) and visualization was accomplished in an iodine chamber. After completion of the reaction, the solid obtained was collected by filtration and washed with warm water. The crude product, so obtained was purified by crystallization with ethanol to afford pure product.

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; Jain, Renuka; Sharma, Kanti; Kumar, Deepak; Tetrahedron Letters; vol. 53; 46; (2012); p. 6236 – 6240,5;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8.

To a solution of 6-bromo-4-chlorobenzo[c][l ,2,5]oxadiazole (372 mg, 1.6 mmol) in NMP (3 mL) in a 4 dram vial was added isoindoline (238 mg, 2 mmol) and triethylamine (400 muL¡¤, 2.9 mmol). A cap was tightly fitted and the reaction was heated at 85 C O/N. The reaction was worked up by diluting with EtOAc (60 mL) and washing with 1M HCl (3 x 20 mL) and brine (1 x 20 mL). The organic phase was dried with MgS04 filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (9 : 1 Hex / EtOAc) to give 208 mg (41 % yield) of 6-bromo-4-(isoindolin-2-yl)benzo[c][l ,2,5]oxadiazole. lU NMR (300 MHz, CDC13) delta = 7.38 (m, 4H), 7.26 (s, 1H), 6.14 (s, 1H), 5.14 (s, 4H). To a solution of the afore mentioned material, (200 mg, 0.6 mmol) in DME (4 mL) / Na2C03 (0.9 mL) was added 3- formyl-phenylboronic acid (134 mg, 0.9 mmol) and Pd(P(Ph)3)4 (35 mg). The flask was then fitted with a reflux condenser, purged with argon and heated to 115 C O/N. The reaction was worked up by diluting with 1 M NaOH (40 mL) and extracting with EtOAc (3 x 20 mL). The organic phase was washed with brine, dried with MgS04 and concentrated in vacuo. The crude material was fused to Si02 (2 g) and purified by flash column chromatography (2:1 DCM / Hex) to give 190 mg (92 % yield). 1H NMR (500 MHz, CDC13) delta = 10.18 (s, 1H), 8.24 (m, 1H), 7.99 (dm, J = 8 Hz, 2H), 7.70 (t, J = 7 Hz, 1H), 7.44 (m, 4H), 7.26 (s, 1H), 6.30 (s, 1H), 5.25 (s, 4 H). To a stirring solution of the afore mentioned material, (190 mg, 0.55 mmol) and Rupert’s reagent (150 mg, 1.1 mmol) in DCM (5 mL) at 0 C was added TBAF (0.1 mL, 1 M THF, 0.1 mmol). After 30 min at low temperature the cold bath was removed and the reaction was allowed to come to RT. After 3 hours an excess of TBAF was added and the reaction was diluted with DCM. The organic phases were washed with saturated NFLCl, brine, and then dried with MgS04 and concentrated in vacuo. The crude material was passed through a plug of Si02 (DCM)and then purified by flash column chromatography (2: 1 DCM / Hex). 1H NMR (500 MHz, CDCI3) delta = 7.84 (s, 1H), 7.77 (dt, J = 7 Hz, 2 Hz, 1H), 7.60 (m, 2H), 7.43 (m, 4H), 7.23 (s, 1H), 6.25 (s, 1H), 5.31 (s, 4H), 5.2 (m, 1H), 2.68 (s, 1H).

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 496-12-8.

Reference:
Patent; TREVENTIS CORPORATION; REED, Mark, A.; WOOD, Thomas, K.; BANFIELD, Scott, C.; BARDEN, Christopher, J.; WO2014/31873; (2014); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-74-4, These common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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.

Under an inert gas atmosphere, add a stir bar, 0.75 mmol of 1-methylisatin, 0.05 mmol of DBU, and 2 mL of acetonitrile to the autoclave, and then fill the autoclave with carbonyl sulfide gas of about 0.8MPa. After stirring for 24 hours at , the autoclave was opened, the reaction solution in the autoclave was dissolved in 2 ml of dichloromethane and transferred to a 50 ml round-bottomed single-neck flask, with (3¡Á2 ml) dichloromethane The autoclave was rinsed, and then the solvent was removed in vacuo to obtain a crude product.The crude product was separated and purified by column chromatography (eluent: dichloromethane).The yield was 91%.

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 2058-74-4.

Reference:
Patent; Dalian University of Technology; Zhou Hui; Chen Wei; Lv Xiaobing; (10 pag.)CN111233741; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2913-97-5,Some common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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.

A mixture of intermediate B2 (i .46 g, i equiv), hydroxylamine hydrochloride (0.64 g, i .2 equiv), anhydrous K2C03 (i.6 g, i.5 equiv) in absolute methanol (iO ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water, extracted with dichloromethane three times. The organic phase was combined and washed with brine, dried and solvent evaporated to give the title compound as a white solid (0.75 g). ?H-NMR (d5-DMSO, 400 MHz, ca i:i cis-trans isomer) 64.30/4.37 (2xd, 2H, J=4.0), 6.8i/7.35 (2xt, iH, J=4.0), 7.8i-7.88 (m, 4H), iO.86/ii.34 (2xs, iH); MS (El) mlz: 204 (Mj.

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

Reference:
Patent; Shen, Jianhua; Wang, Yiping; Wang, Kai; US2014/171431; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem