Category: 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. 496-12-8

A literature procedure1 was modified by replacing triethylamine with N,N-diisopropylethylamine. To a stirred mixture of tetrahydroisoindoline (0.11 mL, 1.0 mmol), N-Boc-(R)-phenylalanine (265 mg, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (182 mg, 1.0 mmol) and anhydrous 1-hydroxybenzotriazole (203 mg, 1.5 mmol) in N,N-dimethylformamide (3.0 mL) was added N,N-diisopropylethylamine (1.3 mL, 7.5 mmol). The mixture was stirred at 20 for 16 h. The solvent was evaporated and the residue was dissolved in ethyl acetate (20 mL) and the solution was washed with water (2 x 20 mL). The combined aqueous fractions were re-extracted with ethyl acetate (2 x 20 mL) and all the combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2 x 20 mL) then with brine (20 mL) filtered and dried (MgSO4). Column chromatography (25:75 ethyl acetate: dichloromethane) of the residue gave 7c (175 mg, 48%) as a cream solid, m.p. 156-160 (decomp.); 1H NMR (500 MHz, CDCl3) delta 7.30-7.20 (7H, m), 7.16-7.14 (1H, m), 7.22-7.00 (1H, m), 5.36 (1H, d, J=9.0 Hz), 4.88 (1H, d, J=13.8 Hz), 4.82 (1H, d, J=15.9 Hz), 4.68-4.77 (1H, m), 4.63 (1H, d, J=15.9 Hz), 4.06 (1H, d, J=13.8 Hz), 3.10-2.98 (2H, m), 1.40 (9H, s); 13C NMR (125 MHz, CDCl3) delta 170.2, 155.1, 150.8, 136.5, 130.0, 129.3, 128.7, 127.1, 120.6, 116.7, 79.9, 51.0, 49.3, 49.1, 45.5, 41.9, 40.6, 28.4.

Hope you enjoy the show about 496-12-8.

Reference:
Article; Chan, A. W. Edith; Greenwood, Simon O. R.; Hansen, D. Flemming; Marson, Charles M.; Bioorganic and medicinal chemistry letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

While the job of a research scientist varies, most chemistry careers in research are based in laboratories, where research is conducted by teams following scientific methods and standards. , Quality Control of Isoindoline

Will Isoindoline (58 muL, 0.5 mmol),And a stirrer is placed in the reaction tube,After replacing the inert gas,DMF (193 muL, 2.5 mmol) was added, and the reaction tube was sealed.The reaction tube was placed in a 150 C oil bath reactor and the reaction was stirred for 96 hours.After cooling to room temperature, it was diluted with 15 mL of water and extracted with ethyl acetate three times, 15 mL each time.The combined extracts were dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate: petroleum ether = 1:3 (1% triethylamine) as eluent. Get pure.Black oily liquid with a yield of 80%.

As always, wish you can browse a selection of our May HOT articles below about Isoindoline.

Reference:
Patent; Xiangtan University; Gong Xing; Yin Jiawen; Cai Changqun; (15 pag.)CN109293569; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 496-12-8,The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research.

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).

Hope you enjoy the show about 496-12-8.

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

Related Products of 496-12-8, New month, new HOT articles! We are pleased to share a selection of our referee-recommended HOT articles for 2021. We hope you enjoy reading these articles.

Preparation of the title compound was initiated by subjecting the product from step 2 A (0.02 g, 0.03 mmol) to isoindoline (0.01 g, 0.06 mmol) andDBU (0.01 g, 0.06 mmol) in 1 mL DCM at 45 0C for 3 h. Once complete byMS analysis, the reaction was diluted with 10 mL EtOAc and extracted withNaHCtheta3 (2 x 10 mL) and brine (2 x 20 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and then concentrated in vacuo. The residue was purified by silica gel flash chromatography using 70%EtOAc/hexanes affording pyridazinone 4a. (0.01 g, 64 %).MS (ESI) m/z = 755.3 (M+H)+.

As always, wish you can browse a selection of our May HOT articles below about Isoindoline.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WO2008/19266; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In chemical reaction engineering, simulations are useful for investigating and optimizing a particular reaction process or system., Related Products of 496-12-8

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 × 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).

The design and synthesis of related molecules that are more effective, more selective, and less toxic than aspirin are important objectives of biomedical research.Keep reading other articles of Isoindoline.

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

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. 496-12-8

To a stirred solution of [(3S,5S)-5-{[(2S)-2-cyanopyrrolidin-1-yl]carbonyl}-2-oxopyrrolidin-3-yl]acetic acid (265 mg, 0.50 mmol) and HOBt (42 mg, 0.55 mmol) in 1,4-dioxane (3 mL) was added a solution of EDC (105 mg, 0.55 mmol) in CH2Cl2 (3 mL). The mixture was stirred for 10 min at room temperature. Isoindoline (65 mg, 0.55 mmol) in CH2Cl2 (2 mL) was added with stirring. After 16 h, the reaction mixture was washed with saturated aqueous NaHCO3 (10 mL), 1 N aqueous citric acid (10 mL), and brine (10 mL). The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified over silica gel using CH2Cl2/MeOH (98:2) as an eluent to yield compound 1 (128 mg, 0.35 mmol, 70%). 1H NMR (300 MHz, CDCl3): (6/1 mixture of trans/cis amide rotomers) delta 7.30-7.26 (m, 4H), 6.56 (s, 0.86H), 6.06 (s, 0.14H), 4.82-4.77 (m, 4.86H, overlapped two singlet at 4.82, 4.77), 4.60 (d, J=6.6 Hz, 0.14H), 4.55 (d, J=9.0 Hz, 0.14H), 4.40 (dd, J=3.0, 9.0 Hz, 0.86H), 3.61-3.04 (m, 2H), 3.02-2.88 (m, 2H), 2.68-2.36 (m, 3H), 2.29-2.12 (m, 4H). MS (ES+) m/z calcd. for C20H22N4O3: 366.17. found: 367.1 (M+H).

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:
Patent; National Health Research Institutes; US2010/234431; (2010); A1;,
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., 496-12-8

Example 66 Preparation of 2-(4-(2-(Isoindolin-2-yl)ethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one To a suspension of 2-[4-(2-bromoethoxy)-3,5-dimethylphenyl]-5,7-dimethoxy-3H-quinazolin-4-one (0.50 g, 1.15 mmol) in anhydrous DMF (9 mL) was added isoindoline (0.41 mL, 3.46 mmol) and the reaction mixture was stirred at room temperature for 16 hours under nitrogen. The solvent was removed under reduced pressure and the residue was triturated with water (50 mL). The separated solid was filtered, washed with water and ether, and dried under vacuum to give the title compound as a white solid. Yield: 0.45 g (83%). MP 202-202.5 C. 1H NMR (400 MHz, CDCl3): delta 10.09 (br s, 1H), 7.77 (s, 2H), 7.22 (br s, 4H), 6.83 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 4.11 (s, 4H), 4.03 (t, J=6.0 Hz, 2H), 3.96 (s, 3H), 3.93 (s, 3H), 3.22 (t, J=6.0 Hz, 2H), 2.42 (s, 6H).

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 Isoindoline.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8,When developing chemical systems it’s of course important to gain a deep understanding of the chemical reaction process.

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

HPLC of Formula: C8H9N,The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research.

The above compound was prepared as follows using General Procedure G9. lsoindoline (130 mg, 1 mmol) was added to a solution of 3-chloro-4,6-dimethoxy-2- methylbenzoic acid (compound A in general procedure G9, and prepared via the method reported by Clevenger et al. Organic Letters (2004), 6(24), p4459)) (200 mg, 0.87 mmole), diisopropylethyl amine (0.8 mL, 4.5 mmol), and O-(7-azabenzotriazol-1 -yl)-N,N,N’,N’- tetramethyluronium phosphorus pentafloride (HATU) (380 mg, 1 mmol) in 4 mL of DMF under a nitrogen atmosphere. The reaction was allowed to stir at room temperature for 12 hours. Saturated NaHCO3 (30 mL) was added to the reaction mixture to quench the reaction. EtOAc EPO (2 x 50 ml.) was then added to extract the aqueous solution. Dry EtOAc layer over Na2SO4. The Na2SO4 was filtered off and the filtrate was evaporated to give a brown oil residue. The residue was purified by silica gel chromatography (gradient elution 45 ?50% EtOAc in hexanes) to give the desired intermediate product (3-chloro-4,6-dimethoxy-2- methylphenyl)(isoindolin-2-yl)methanone (265 mg, 92% yield). 1H NMR (400 MHz, DMS0-D6) delta ppm 2.18 (s, 3 H) 3.81 (s, 3 H) 3.92 (s, 3 H) 4.39 (d, J=7.07 Hz, 2 H) 4.80 (s, 2 H) 6.76 (s, 1 H) 7.17 – 7.35 (m, 3 H) 7.38 (d, J=7.07 Hz, 1 H): Anal. Calcd for C18H18CINO3: C, 65.16; H, 5.47; N, 4.22. Found: C, 65.05; H, 5.48; N, 4.22.

We very much hope you enjoy reading the articles and that you will join us to present your own research about Isoindoline.

Reference:
Patent; PFIZER INC.; WO2006/117669; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 496-12-8, Having gained chemical understanding at molecular level, chemistry graduates may choose to apply this knowledge in almost unlimited ways, as it can be used to analyze all matter and therefore our entire environment.

(5-bromo-2,4-dihydroxyphenyl)(isoindolin-2-yl)methanone, 7 (PA1): In a 50 mL, three-necked, round-bottomed flask, 5-bromo-2,4-dihydroxybenzoic acid (1.42 g, 5.65 mmol, 1.13 equivalent), l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 1.02 g, 5.25 mmol, 1.05 equivalent) and 1-Hydroxybenzotriazole (HOBT, 776 mg, 5.75 mmol, 1.15 equivalent) were dissolved in dimethylformamide (10 mL) at room temperature. The mixture was stirred at the same temperature for 30 min before isoindoline (596 mg, 5 mmol, 1 equivalent) was added. After 18 h, the reaction mixture was diluted with ethyl acetate (50 mL) and washed sequentially with IN HC1 aqueous solution, saturated aqueous aHC03, and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel; ethyl acetate: hexanes 1 :20 to 1 : 1) to yield PAl (1.17 g, 70% yield). XH NMR (500 MHz, DMSO-d6) delta 10.50 (s, 1H), 10.34 (s, 1H), 7.38-7.36 (m, 2H), 7.34 (s, 1H), 7.29-7.27 (m, 2H), 6.59 (s, 1H), 4.77 (s, 2H), 4.70 (s, 2H); 13C NMR (125 MHz, DMSO-d6) delta 166.6, 155.8, 154.7, 136.9, 131.7, 127.4, 122.9, 117.2, 103.7, 98.6, 52.7 (Rotamers were observed). LRMS (ESI) calculated for [M+H]+ 334.0, found 333.9.

The design and synthesis of related molecules that are more effective, more selective, and less toxic than aspirin are important objectives of biomedical research.Keep reading other articles of Isoindoline.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; CHUANG, David, T.; TSO, Shih-Chia; QI, Xiangbing; GUI, Wen-Jun; WU, Cheng-Yang; CHUANG, Jacinta, L.; TAMBAR, Uttam, K.; WYNN, R., Max; WO2015/89360; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem