Category: 496-12-8

Electric Literature of 496-12-8, The chemical industry reduces the impact on the environment during synthesis 496-12-8, name is Isoindoline, I believe this compound will play a more active role in future production and life.

(Intermediate Example 89) 3-Amino-1-(1,3-dihydroisoindol-2-yl)-3-methylbutan-1-one 2,3-Dihydro-1H-isoindole (543 mg) and 3-amino-3-methylbutanoic acid (700 mg) were dissolved in N,N-dimethylformamide (30 ml). N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (876 mg) and hydroxybenzotriazole (698 mg) were added thereto at 0C, and then the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and water and ethyl acetate were added to the residue. The organic phase was separated, and the aqueous phase was adjusted to pH 9 by adding a saturated sodium bicarbonate solution, and then extracted with ethyl acetate. The extract was dried over sodium sulfate and concentrated under reduced pressure to give the title compound (0.60 g, Y.: 60%) as a brown oily matter. 1H NMR; (CDCl3) delta (ppm): 1.2 (6H, s), 2.4 (2H, s), 4.7-4.8 (4H, m), 7.2-7.3 (4H, m). ESI/MS (m/z): 219 (M+H)+.

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; EP1595866; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of amine (0.2 mmol) and MnCl2¡¤4H2O (5.9 mg, 15 mol%) in DMF (1.0 mL) was stirred in a sealed microwave reaction tube under an atmosphere of argon at 150 C for 10 h. The mixture was cooled to r.t., and water (10 mL) was added; the mixture was extracted with EtOAc (3 ¡Á 15 mL). The combined organic layers were dried (anhyd Na2SO4), the solvent was evaporated under vacuum, and the crude product was purified by preparative TLC (silica gel, petroleum ether/EtOAc) to obtain the pure product.

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

Reference:
Article; Ma, Juan; Zhang, Jingyu; Gong, Hang; Synthesis; vol. 51; 3; (2019); p. 693 – 703;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, name is Isoindoline, 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. category: indolines-derivatives

General procedure: A mixture of the amine (2.0 mmol), EDC (2.6 mmol), and HOBt (3.3 mmol) were purged with nitrogen before the addition of the acid (2.6 mmol) and THF (10 ml). DIPEA (11.0 mmol) was then added and the reaction was stirred at room temperature for 16 h. The reaction mixture was poured into a separatory funnel containing saturated NH4Cl (10 ml) and extracted with ethyl acetate (3 ¡Á 30 ml). The combined organic layers were dried over Na2SO4, concentrated under vacuum. Purification on silica gel yielded the desired product.

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Awuah, Emelia; Ma, Eric; Hoegl, Annabelle; Vong, Kenward; Habib, Eric; Auclair, Karine; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3083 – 3090;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

3-lodo-4-methylbenzoic acid (262 mg, 1.0 mmol), isoindoline (284 uL, 1.5 mmol), and triethylamine (420 uL, 3.0 mmol) were dissolved in 10 ml. Of CH2CI2 and treated with HOBt (203 mg, 1.5 mmol) and EDC (288 mg, 1.5 mmol). The reaction were stirred at room temperature overnight. The reaction mixture was concentrated, diluted with EtOAc, and washed with water, 1 N HCI, and brine. The organic layer was dried (MgSO4), filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (CH2CI2/Et0Ac) to yield 301 mg (83%) of the product as a tan solid. MS (+ESI): m/z 363.9 [M+H]+.

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

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
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.

N-Nitrosoisoindoline 18: To a solution of isoindoline 45 in a mixture of 10 mL of acetic acid and 20 mL of water, an aqueous solution of NaNO2 (1.53 g, 22.2 mmol) in 10 mL of water was added at 0 C. The whole was stirred for 2 h, then extracted with CH2Cl2, and the organic layer was washed with 2 N aqueous NaOH, 0.5 N aqueous HCl, brine, and dried over sodium sulfate. The solvent was evaporated to give a residue, which was chromatographed (hexane: AcOEt = 1: 4 to 1: 3) to give 18 as an oil (1.32 g, 8.91 mmol, 45% from alpha,alpha-dibromo-o-xylene). Mp: 85-89 C (recrystallized from MeOH, grayish needles). MS ([M+H]+): 149. 1H NMR (400 MHz, CDCl3): delta 7.40-7.31 (4H, m), 5.63 (2H, s), 4.90 (2H, s).

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:
Article; Ohwada, Tomohiko; Ishikawa, Satoko; Mine, Yusuke; Inami, Keiko; Yanagimoto, Takahiro; Karaki, Fumika; Kabasawa, Yoji; Otani, Yuko; Mochizuki, Masataka; Bioorganic and Medicinal Chemistry; vol. 19; 8; (2011); p. 2726 – 2741;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

Triethylamine (0.33 ml, 2.37 mmol) and isoindoline (0.27 ml, 2.38 mmol) were added in turn to a solution of methyl ester of 5-chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid (820 mg, 2.25 mmol) in dimethyl sulfoxide (5 ml) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was cooled with ice and ice water (50 ml) was added thereto. The mixture was stirred and the precipitates were filtered, washed with water and dried. The resultant yellow crystals were purified by column chromatography on silica gel (n-hexane/ethyl acetate = 15) to give methyl ester of 5-chloro-2-(1,2,3,4-tetrahydroisoquinolinio)-3-nitrobenzoic acid (608 mg, 81 %) as yellow crystals. m.p.: 114 – 115 C; IR (Nujol): 1743, 1705, 1603, 1589, 1529, 1503 cm-1; APCI-MS m/z: 333[M+H]+.

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; Endo, Hitoshi; EP1481965; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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 6-bromo-4-chlorobenzo[c][1,2,5]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*20 mL) and brine (1*20 mL). The organic phase was dried with MgSO4 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][1,2,5]oxadiazole. 1H NMR (300 MHz, CDCl3) delta=7.38 (m, 4H), 7.26 (s, 1H), 6.14 (s, 1H), 5.14 (s, 4H).

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.; Yadav, Arun; Lu, Erhu; Wu, Fan; (204 pag.)US2017/174641; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 496-12-8, name is Isoindoline, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 496-12-8

General procedure: To a solution of compound 5 (1.0eq.) and Ia-f (1.0eq.) was added K2CO3 (2.2eq.) in anhydrous DMF at RT. After stirring for 5-7h, the reaction was diluted with water and the precipitation was filtered to afford the crude targets. Then the crude target was purified by flash column chromatography (EtOAc : PE=1 : 5) to afford the compounds 6a-f. Targets 7a-e, 8a-d and 9a-c were obtained as the procedure for 6a-f by the reaction of compound 5 witha-e, IIIa-d and IVa-c.

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, 496-12-8, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Apeng; Yang, Yang; Jun, Yangsheng; Wang, Bin; Lv, Kai; Liu, Mingliang; Guo, Huiyuan; Lu, Yu; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 2073 – 2084;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, name is Isoindoline, 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. 496-12-8

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1 H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1H, s), 10.32 (1 H, s), 7.36 (1H, br.s), 7.35 (1 H, s), 7.28 (3H, br.s), 6.59 (1 H, s), 4.77 (2H, br.s), 4.71 (2H, br.s). MS: [M+H]+ 332/334.

Statistics shows that 496-12-8 is playing an increasingly important role. we look forward to future research findings about Isoindoline.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
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