Month: May 2021

Electric Literature of 3416-57-7, 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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

2-((4-Methyl-2.5-dioxoimidazolidin-4-yl)methylcarbamoyl)benzoic acid [0180] Phthalimido acetone (27-1) (14.2 g, 70 mmol, 1 eq.), ammonium carbonate (23.5 g, 245 mmol, 3.5 eq), potassium cyanide (6.8 g, 105 mmol, 1.5 eq.) in EtOH (70 mL) and H2O (70 niL) were heated at 75 0C for 18 h in a sealed tube. The reaction mixture was cooled to room temperature and the volatiles were evaporated in vacuo. The reaction mixture was partitioned between ethyl acetate (150 mL) and H2O (100 mL). The aqueous phase was adjusted to pH 4 and extracted with more ethyl acetate (2 x 150 mL). Organic layers were combined, dried (MgStheta4) and concentrated in vacuo to yield the crude product (27-2), which was directly used in the next step. Yield: 12.33 g (61%). 1H-NMR (400 MHz, CD3OD^) delta 7.60-7.41 (m, 4H), 3.70 (d, IH), 3.56 (d, IH), 1.44 (s, 3H). LCMS – [M+H] m/z 292.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Oxopropyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVABAY PHARMACEUTICALS, INC.; JAIN, Rakesh, K.; LOW, Eddy; FRANCAVILLA, Charles; SHIAU, Timothy P.; KIM, Bum; NAIR, Satheesh, K.; WO2010/54009; (2010); A1;,
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Synthetic Route of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 mixture of isatin (1 equiv.) and phenyl acetylene (1.2 equiv.) in water (3 mL), CuWO4 (10 mol%) and DABCO (40 mol%) were added at room temperature and the mixture was heated at 60 C for 2 to 5 h. After completion of reaction (monitoring by TLC) mixture was cooled to room temperature and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography to give 3-hydroxy-3-(phenylethynyl)indolin-2-ones (3a-3u).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 104618-31-7

To a solution of 1.534 g (6.26 mmol) of 2-(4-Hydroxy-cyclohexyl)-isoindole-1,3-dione in 60 mL THF was added 0.553 g (13.8) NaH (60% in oil) and reaction mixture stirred under N2 until gas formation ceased. The mixture was cooled to 0 C. and 3.56 g (25.1 mmol) MeI was added and the reaction was stirred at 25 C. for 24 hours. The mixture was then poured into 180 mL sat. NH4Cl(aq) and extracted 3 times with DCM. The organic layers were dried over Na2SO4, concentrated and then purified via chromatography (50% EtOAc/Hex) to give 908 mg of 2-(4-Methoxy-cyclohexyl)-isoindole-1,3-dione (48.3% yield, LCMS (m/z): M+H=301.1). That was dissolved in 40 mL EtOH and 324 mg (8.76 mmol) Hydrazine was added. The reaction mixture was stirred at 65 C. for 3 hours. By the end of the 3 hours the solution was mostly white solid and a little liquid. The reaction was filtered and washed 3 times with 30 mL MeOH and concentrated to give 450 mg of crude product of 4-Methoxy-cyclohexylamine (ca. 100% yield). LCMS (m/z): M+H=130.2.

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 104618-31-7.

Reference:
Patent; Huang, Kenneth He; Ommen, Andy J.; Barta, Thomas E.; Hughes, Philip F.; Veal, James; Ma, Wei; Smith, Emilie D.; Woodward, Angela R.; McCall, W. Stephen; US2008/269193; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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 2913-97-5, SDS of cas: 2913-97-5

Example 12d (0.4 g, 0902 mmol) and 2-(l,3-dioxo onidQlm-2- i)acetaldehyde (0.683 g, 3 J61 mmol) were combined in tetral^drof ran (9 J02 mL) under nitrogen , cooled to 0 * C and treated drop-wise with 1M ntaniuin(I V) chloride in die hloro me thane (3 J61 mL, 3.61 mmol) to give an opaque red solution. The sotitionwas stirred for 72 hours at ambient temperature and partitioned b etween ethyl acetate and water. The organic layer was was hed with s aturated aqueous s odium chloride, dried over arLhydrous sodium sulfate, filtered and concentrated. -ificationby chromatography (siEca gel, 0.5-5percent methanol in dichloiomethane) afforded the title confound as a yellow powder (0.45 g, 81percent). NMR (500 MHz, DMS 0-^) 6 1 1.78 ^, ; = 1 S3 Hz, 1 7.93 (d, J = 1 .53 Hz, 1H), 7B1 – 7.85 (m, 4 7.76 (s, l H), 7.24 – 7.30 (m, 1 H), 721 (dd, J = 824, 1.83 Hz, 1H), 7.09 – 7.15 (m, 1H) 699 – 7.05 (m, 1 6.96 (d, J = 2.44 Hz, 1 HI 6.92 (d, J = 824 Hz, 1 HI 5.44 (dd, J = 9.92, 5 4 Hz, 1 HI 4.51 – 4.56 (m, 1H), 4.44 – 4.48 (m, 1 3.87 (dd, J = 13.28, 5.34 Hz, 1 HI 3 J66 (S, 3H), 3 2 (dd, J = 13.28, 10.22 Hz, 1H), 2.98 (s, 3H) . Xi (EpsilonXi 1+) m/z 615 (M+H) 1.

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; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
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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. 603-62-3, name is 3-Nitrophthalimide, A new synthetic method of this compound is introduced below., COA of Formula: C8H4N2O4

Step 1: To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C. for 3 hrs, and then heated to 30 C. for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C. for 1 hr. The suspension was filtered and washed with cold water (2*10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 7.69 (brs, 1H, NHH), 7.74 (t, J=8 Hz, 1H, Ar), 7.92 (dd, J=1, 8 Hz, 1H, Ar), 8.13 (dd, J=1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Muller, George; Man, Hon-Wah; Cohen, Benjamin M.; Li, Ying; Xu, Jean; Leong, William W.; US2012/232100; (2012); A1;,
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Synthetic Route of 7477-63-6, The chemical industry reduces the impact on the environment during synthesis 7477-63-6, name is 7-Chloroisatin, I believe this compound will play a more active role in future production and life.

General procedure: For compound 3, arenesulfenyl chloride (5 mmol) was added dropwise to a solution of isatin or isatin derivatives (5 mmol) and triethylamine (5 mmol) in N,N-dimethylformamide (DMF, 5 mL) at room temperature. Stirring was continued for an additional 30 min and then the mixture was poured into ice water (20 mL). The yellow precipitates were collected by filtration and recrystallized from ethanol to give pure 3a-3m.

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shang, Jian-Li; Guo, Hui; Li, Zai-Shun; Ren, Biao; Li, Zheng-Ming; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 724 – 727;,
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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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., name: N-Vinylphthalimide

b) Ethyl 2-[3-(2-amino-ethyl)-phenoxy]-2-methyl-propionate (13b); 10d (14 g, 49 mmol) is placed in the presence of N-vinylphthalimide (11 g, 63 mmol) and 27 ml (194 mmol) of triethylamine in 160 ml of DMF. Pd(OAc)2 (0.3 g) and P(oTol)3 (0.4 g) are added and the reaction medium is stirred for 10 h at 110 C. The reaction medium is dry concentrated and the residue obtained is taken up in water and extracted with AcOEt. After drying on MgSO4, the organic phases are dry concentrated and the oil isolated is purified by flash chromatography on silica (heptane:AcOEt 90:10). 11.5 g of oil is obtained (62% yield) then placed in a solution of 70 ml of THF and 70 ml of EtOH in the presence of Pd/C under hydrogen at 6 bar. This mixture is stirred for 72 h at ambient temperature. After filtration on celite, the reaction medium is dry concentrated and the residue obtained is purified by flash chromatography on silica (petroleum ether:AcOEt 80:20). 10.9 g of clear oil are obtained (yield=94%). This oil is then placed in 140 ml of EtOH in the presence of 3.5 ml of hydrazine hydrate then this solution is heated at reflux for 4 h. After filtration of the insolubles, the reaction medium is dry concentrated and then the residue obtained is purified by flash chromatography on silica (CH2Cl2:MeOH:NH4OH 90:9:1). 5.7 g of intermediate 13b are thus isolated in the form of an oil (yield=80%). TLC silica gel 60 F 254 Merck, CH2Cl2:MeOH:NH4OH 90:9:1, Rf=0.28.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Pierre Fabre Medicament; US2008/167313; (2008); A1;,
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Indoline | C8H9N – PubChem

Related Products of 20780-72-7, 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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Isatin 1 (147.1 mg, 1 mmol), (E)-1-phenylpent-2-ene-1,4-dione (2a, 348.4 mg, 2 mmol), and thiourea I (57 mg, 0.1 mmol) were cooled to -20 °C, dissolved in toluene (3 mL), and the mixture was stirred at -20 °C for 24 h. The progress of the reaction was monitored by TLC and NMR spectroscopy. The product was isolated by direct column chromatography on silica gel (CH2Cl2/EtOAc 95:5 to 85:15)

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Trubitson, Dmitri; ?ari, Sergei; Kaabel, Sandra; Kudrjashova, Marina; Kriis, Kadri; Jaerving, Ivar; Pehk, Tonis; Kanger, Tonis; Synthesis; vol. 50; 2; (2018); p. 314 – 322;,
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Adding a certain compound to certain chemical reactions, such as: 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, 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 35197-64-9, Safety of 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid

Step b: Preparation of tert-but 2-bromo-4-(l,3-dioxo-l,3-dihydro-2H-isoindol-2-yl) butanoate To a solution of compound obtained from Step a (180 mg, 0.576 mmoles) in tetrahydrofuran (5 mL) was added Boc anhydride (1 mL, 0.461 mmoles) and N,N- dimethylaminopyridine (7 mg, 0.057 mmoles). The reaction mixture was allowed to stir at room temperature for about 18 hours. After completion of reaction, solvent was azeotropically distilled using toluene and ethyl acetate to obtain a crude product. The crude product was purified on silica gel column using 20% ethyl acetate: hexane as eluent to get the desired product. Yield: 180 mg

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; RANBAXY LABORATORIES LIMITED; KHERA, Manoj Kumar; PALLE, Venkata P.; SATTIGERI, Viswajanani; SATTIGERI, Jitendra; SONI, Ajay; RAUF, Abdul Rehman Abdul; SIVAKUMAR, R.; REDDY, Ranadheer R.; MUSIB, Arpita; CLIFFE, Ian A.; BHATNAGAR, Pradip Kumar; RAY, Abhijit; SRIVASTAVA, Punit; DASTIDAR, Sunanda Ghosh; WO2012/38944; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. COA of Formula: C8H4BrNO2

5-bromo-2-ethylisoindoline-1,3-dioneTo a solution of 5-bromoisoindoline-1 ,3-dione (1 130 mg, 5 mmol) in THF (25 mL) was added iodoethane (0.606 mL, 7.50 mmol) and then slowly was added NaH (144 mg, 6.00 mmol). The resulting reaction was stirred at RT for 22 h. To the reaction mixture was added DMF (2 mL) then stirred at RT for 23 h. To the reaction mixture was added more DMF (3 mL) then was stirred at RT for 120 h. The reaction mixture was diluted with H20 (20 mL), acidified with HCI (1 mL, 1.0 N), extracted with EtOAc (3 x 20 mL), washed with brine (20 mL), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product 5-bromo-2-ethylisoindoline-1 ,3-dione (899.7 mg, 3.54 mmol, 70.8 % yield). LC-MS mlz 254.1 (M+H)+, 0.90 min (ret. time).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
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