Category: 496-12-8

Related Products of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

General procedure: To a stirred solution of compound 11 (100 mg, 0.245 mmol) in DMF (4 mL) was added diisopropylethylamine (DiPEA) (95 mg, 0.735 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (112 mg, 0.294 mmol) followed by addition of aryl or aliphatic amines (12a-m) (0.279 mmol) and stirred at room temperature for 18 h. After completion reaction mixture was poured into ice cold water extracted with ethyl acetate (2 ¡Á 15 mL), combined extracts were washed with brine solution, dried over anhy. Na2SO4 and concentrated under reduced pressure to afford crude product. This crude compound was purified by column chromatography (elutent:2 % methaol: CH2Cl2) to affords pure compounds 13a-m as yields of the products varied between 80-94 %. By adapting this procedure the compounds 13a-13m were synthesized (Scheme-II).

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

Reference:
Article; Tharikoppula, Giri; Eppakayala, Laxminarayana; Maringanti, Thirumala Chary; Kamalapuram, Chiranjeevi; Kudle, Karunakar Rao; Asian Journal of Chemistry; vol. 29; 7; (2017); p. 1515 – 1521;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Application In Synthesis of Isoindoline

Part B. To a solution of the isoindoline (5.40 g, 21.3 mmol) made above in EtOH (266 mL) under N2 was added 20% Pd(OH)2/C (3.00 g, 4.25 mmol). The reaction mixture was hydrogenated at 45 psi for 1 h. TLC analysis indicated that the nitro functionality was reduced and the Bn group was still intact. Therefore, concentrated HCl (1.6 mL, 19.1 mmol) was added to the reaction mixture and hydrogenation (50 psi) was continued overnight. The mixture was filtered through Celite, washed with MeOH, and the filtrate was concentrated to one fourth of the volume. The precipitate was filtered off to provide the 5-aminoisoindoline.HCl (1.32 g, 36% yield): 1H NMR (500 MHz, CDCl3) delta9.88 (s, br, 2H), 7.00 (d, 1H), 6.54 (m, 2H), 5.44 (s, br, 2H), 4.32 (s, 2H), 4.28 (s, 2H); ESI MS m/z 135 (M-HCl+H)+.

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

Reference:
Patent; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; US2003/191115; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 496-12-8, name is Isoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H9N

3 – ((2S, 3R, 4R, 5S, 6R) -3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran- 2- yl] benzylaldehyde 925 milligrams (2.12 millimoles) were dissolved in 20 milliliters of dichloroethane, To the reaction mixture was added 292 mg of isoindoline (2.45 mmol), 254 mg of acetic acid (4.24 mmol) and sodium triacetoxyborohydride 674 milligrams (3.18 millimoles) was added and the drug And stirred at 20 [deg.] C for about 3 hours. The reaction mixture solution was heated to 0 o After cooling to C, saturated sodium bicarbonate And then extracted with ethyl acetate. The organic solution was dried over anhydrous magnesium sulfate and filtered The reaction mixture was concentrated and then purified by column chromatography to obtain the compound 850 mg (yield: 74.6%) was obtained Method B)

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

Reference:
Patent; Samjin Pharmaceutical Co., Ltd.; Cho, Eui-Hwan; Shin, Hui-Jong; Kwon, Ho-Seok; Lee, Jae-Woong; Joo, Jeong-Ho; Lee, Keun-Kuk; Kim, Jong-Min; Kim, Hyun-Tae; Kim, Jae-Eon; Lee, Jung-Rok; Jang, Beom-Hyeon; (37 pag.)KR2016/97861; (2016); A;,
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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., name: Isoindoline

General procedure: A mixture of tert-butyl (2-amino-1-(thiophen-3-yl)ethyl)(methyl)carbamate (33) (310 mg, 1.21 mmol) and N,N-diisopropylethylamine (300 muL, 1.73 mmol) in CH2Cl2 (15 mL) was purged with argon and cooled to 0 C. A solution of 4-nitrophenylchloroformate (244 mg, 1.21 mmol) in CH2Cl2 (5 mL) was added, and resulting reaction mixture was stirred at – 70 C for 30 min. After this time, 5-fluoroisoindoline hydrochloride (150 mg, 0.86 mmol) was added, followed by N,N-diisopropylethylamine (450 muL, 2.60 mmol). The resulting mixture was stirred for 20 h at room temperature. A saturated NaHCO3 solution (10 mL) was added, and the resulting suspension was extracted with CH2Cl2 (3 x15 mL). The combined organic extracts were washed with water (30 mL), then with a brine solution (20 mL) and dried over solid anhydrous Na2SO4. After filtration, the volatiles were removed in vacuo, and the residue was purified by flash chromatography using eluent from CH2Cl2 to CH2Cl2/MeOH (1:1), then reverse phase chromatography using eluent from H2O/MeCN (9:1) MeCN, to give tert-butyl (2-(5-fluoroisoindoline-2-carboxamido)-1-(thiophen-3- yl)ethyl)(methyl)carbamate (34) (150 mg, 41% yield). 300 MHz 1H-NMR (CDCl3, ppm): 7.32 (dd, J=5.0, 2.9 Hz, 1H) 7.24-7.14 (m, 2H) 7.05-6.91 (m, 3H) 5.63-5.41 (m, 1H) 5.09- 4.91 (m, 1H) 4.68 (s, 2H) 4.64 (s, 2H) 4.15-3.88 (m, 1H) 3.77-3.57 (m, 1H) 2.56 (s, 3H) 1.45 (s, 9H); ESI-MS (m/z): 420 [M+H]+; melting point: 182-184 C. Isoindoline (500 mg, 4.20 mmol) and tert-butyl (2-amino-1-phenylethyl)(methyl) carbamate (36) were reacted in CH2Cl2 using procedure described for compound (34) to obtain tert-butyl (2-(isoindoline-2-carboxamido)-1-phenylethyl)(methyl)carbamate (37) (1.49 g, 90% yield). 400 MHz 1H-NMR (CDCl3, ppm): 7.41-7.33 (m, 2H) 7.33-7.29 (m, 2H) 7.29- 7.23 (m, 5H) 5.62-5.41 (m, 1H) 5.19-5.00 (m, 1H) 4.71 (s, 4H) 4.19-3.93 (m, 1H) 3.84-3.62 (m, 1H) 2.55 (s, 3H) 1.46 (s, 9H); ESI-MS (m/z): 396 [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; MEBIAS DISCOVERY LLC; TOUNGE, Brett A.; BAYOUMY, Shariff; KUO, Lawrence C.; DAX, Scott; (93 pag.)WO2018/45229; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, 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 496-12-8 as follows.

(1) Triethylamine (3.48 mL, 25.0 mmol) was added to a solution of isoindoline (4.98 g, 25.0 mmol) in chloroform (100 mL) at room temperature and the mixture was cooled in ice. Trichloroacetic acid chloride (2.79 mL, 25.0 mmol) was added dropwise thereto and the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1) to afford 2,2,2-trichloro-1-(1,3-dihydro-2H-isoindol-2-yl)ethanone as a purple powder (6.59 g).

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; BUSUJIMA, Tsuyoshi; OI, Takahiro; TANAKA, Hiroaki; SHIRASAKI, Yoshihisa; IWAKIRI, Kanako; SATO, Nagaaki; TOKITA, Shigeru; EP2687507; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Recommanded Product: Isoindoline

To a stirred suspension of methyl 4-(bromomethyl)-3-methoxybenzoate (0.53 g, 2.04 mmol, 1 eq.) and potassium carbonate (0.56 g, 4 mmol, 2 eq.) in N,N-dimethylformamide (5 mL) was added isoindoline (280 mu^, 2.45 mmol, 1.2 eq.). The resulting mixture was then stirred at room temperature for 17 hours. The solvent was removed in vacuo and the crude product was partitioned between water and dichloromethane, the layers were separated and the aqueous phase extracted with dichloromethane. The combined extracts were dried with magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography using a 10 – 100 % ethyl acetate in wo-hexane gradient to afford methyl 4- (isoindolin-2-ylmethyl)-3-methoxybenzoate as a red liquid (0.417 g, 70 % yield). NMR (400 MHz, CDC13) 7.66 (1H, d, J=7.8 Hz), 7.55-7.53 (2H, m), 7.18 (4H, s), 4.0-3.98 (6H, m), 3.92-3.91 (6H, m).

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; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 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.

A solution of 4-formylbenzene sulfonyl chloride (1) (0.50 g, 2.44 mmol) in dichloromethane (5 mL) was treated with isoindoline (0.32 g, 2.68 mmol) and triethylamine (0.41 mL, 2.93 mmol). The resultant mixture was stirred at room temperature for 1 h. A saturated aqueous solution of sodium bicarbonate (10 mL) was added. The product was extracted three times with 10 mL of dichloromethane. The combined organic layers were dried over potassium carbonate, filtered and concentrated in vacuo. The crude material (0.67 g, 96% yield) was used in the next reaction without purification: Crude 1H NMR (400 MHz, CDCl3) delta 10.06 (s, IH), 8.05-8.00 (m, 4H), 7.25-7.20 (m, 2H), 7.20-7.14 (m, 2H), 4.66 (s, 4H); ESI+ MS: m/z (rel intensity) 288.0 (100, [M+H]+).

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

Reference:
Patent; METASTATIX, INC.; WO2008/109154; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

To a stirred solution of isoindoline (2 g, 16.8 mmol) at 0 0C5 was added slowly concentrated H2SO4 (10 mL). Then a mixture of 70% HNO3 (2.1 mL, 33.6 mmol) and concentrated H2SO4 (2 mL) was added. After addition the mixture was stirred at 00C for 30 min. The reaction mixture was poured into ice water. The mixture was carefully neutralized with 50% aq. NaOH to pH 10 and extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 5-nitroisoindoline as a brown solid. LCMS calc. = 165.1; found = 164.9 (M+H)+. 1H NMR (500 MHz5 CDCl3): delta 8.11 (d, J= 8.0 Hz, 2 H); 7.39 (d, J= 7.8 Hz, 1 H); 4.33 (s, 4 H); 2.31 (br s, 1 H).

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

Reference:
Patent; MERCK & CO., INC.; WO2007/81569; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

Intermediate 7 2-(4-bromophenyl)-1-(isoindolin-2-yl)ethanone [0500] [0501] To a mixture of 2-(4-bromophenyl)acetic acid (300 mg, 1.395 mmol), isoindoline (183 mg, 1.535 mmol), and HATU (796 mg, 2.093 mmol) in DMF (5 mL), was add DIEA (0.487 mL, 2.79 mmol). The mixture was stirred at rt overnight. The reaction mixture was quenched with water, then extracted with EtOAc. The organic phase was washed with 10% LiCl, brine, and concentrated. The residue was purified via flash chromatography (EtOAc/hexane) to afford 390 mg (88%) of Intermediate 7. [0502] MS (ESI) m/z: 316.0 (M+H)+.

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

Reference:
Patent; Glunz, Peter W.; Zou, Yan; Quan, Mimi L.; US2014/206686; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 496-12-8, 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 496-12-8 as follows.

Example 17Synthesis of 5-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)sulfonyl)-2-(phenylsulfonyl)isoindolineReagents MW Reagent/raw material (g/mole) Quantity moles Isoindoline 119.16 0.5 g 4.2 benzenesulfonyl chloride 176.62 1.1 g 6.3 2-(phenylsulfonyl)isoindoline 259.32 0.54 g 2 sulfurochloridic acid 116.52 5 mL excess 2-(phenylsulfonyl)isoindoline-5- 357.83 0.05 g 0.139 sulfonyl chloride 2,3- 136.15 0.024 g 0.18 dihydrobenzo[b][1,4]dioxineAlCl3 133 0.037 0.27 Step 1: Isoindoline was dissolved in 5 mL dry pyridine, and benzenesulfonyl chloride was dropped in. The reaction was stirred overnight at room temperature and an intense red color developed. When complete as determined by HPLC using the protocol of Example 1, as well as by LCMS, the crude reaction mixture was poured into 100 mL cold 1M KHSO4, and extracted twice with 50 mL CH2Cl2. The organic phase was evaporated and the evaporation residue was purified by CombiFlash (PE/EtOAC) providing 1.1 g pure product (100% yield).

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Becker, Oren M.; Shitrit, Alina; Schutz, Nili; Ben-Zeev, Efrat; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Aizikovich, Alex; Sherman, Daniel; Behar, Vered; Kashtan, Osnat; US2012/108631; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem