Tag: M.W=100-200

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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H9NO2

General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

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 39603-24-2.

Reference:
Article; Dandia, Anshu; Singh, Ruby; Khan, Shahnawaz; Kumari, Sukhbeer; Soni, Pragya; Tetrahedron Letters; vol. 56; 30; (2015); p. 4438 – 4444;,
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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9NO3

Indolinone 1 (1000 mg, 52.3 mmol) was suspended in acetic anhydride (10 mL) and refluxed at 130 C for 8 h. The reaction mixture was allowed to cool to 50 C and (triethoxymethyl)benzene(2930 mg, 131 mmol) was added. The resulting reaction mixture was stirred at 120 C for 6 h. Then, volatiles were removed in vacuo and petroleum ether was added to the obtained residue. After triturating for 15 min, the separated solids were filtered and washed with petroleum ether and then dried under vacuum to afford 974 mg (51%) of title compound.

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:
Article; Edupuganti, Ramakrishna; Taliaferro, Juliana M.; Wang, Qiantao; Xie, Xuemei; Cho, Eun Jeong; Vidhu, Fnu; Ren, Pengyu; Anslyn, Eric V.; Bartholomeusz, Chandra; Dalby, Kevin N.; Bioorganic and Medicinal Chemistry; vol. 25; 9; (2017); p. 2609 – 2616;,
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. 2058-74-4, name is 1-Methylisatin, A new synthetic method of this compound is introduced below., Product Details of 2058-74-4

General procedure: To a magnetically stirred mixture of isatins (1 mmol) and IL I (12.6 mg, 0.05 mmol) were added alkyl-malonates (1 mmol) or 1,3-dicarbonyl compounds (1 mmol) and then the reaction mixture was stirred at room temperature . After completion of the reaction (monitored by TLC), EtOAc was added to the reaction mixture, and [TBD][TFA] was removed by filtration and washed with EtOAc (2 5 ml).The filtrate was evaporated under reduced pressure to give the solid product as a residue in almost pure form. If necessary, the product could further be purified byrecrystallization from ethanol.

The synthetic route of 2058-74-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baghbanian, Seyed Meysam; Tajbakhsh, Mahmood; Farhang, Maryam; Comptes Rendus Chimie; vol. 17; 12; (2014); p. 1160 – 1164;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 16800-68-3, These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, 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: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 59-48-3, 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 59-48-3 as follows.

3-Methyl-1,3-dihydro-indol-2-one A solution of oxindole (665 mg, 5.0 mmol) in THF (10 ml) was treated dropwise with n-BuLi (4.4 ml, 11.0 mmol) at -78 C., stirred for 30 min. at -78 C. To the reaction methyliodine (2 ml) was added dropwise at -78 C. The resulting solution was warmed up to room temperature. The mixture was quenched with water. The reaction solution was partitioned between ethylacetate and water. The organic layer was washed (brine), dried (Na2SO4), filtered and concentrated under vacumm. Purification on silica gel with 30% ethyl acetate/hexane to provide the title compound (630 mg, 86%). MS (DCI/NH3) m/e 148 (M+1)+.

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Safety of 1-Methylisatin

A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%). Other compounds were prepared similarly, and compounds 1a-1i are all known compounds.1

The synthetic route of 1-Methylisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roh, Hwa Jung; Kim, Gieun; Cho, Sung; Ryu, Ji Yeon; Lee, Junseong; Kim, Jae Nyoung; Tetrahedron Letters; vol. 59; 15; (2018); p. 1484 – 1488;,
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 7477-63-6 as follows. Product Details of 7477-63-6

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 ¡ãC (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 2 (200mg, 1.04mmol), neopentyl glycol (108mg,1.04mmol) and p-toluenesulfonic acid (25mg, 145mumol) were suc-cessively added and dissolved in cyclohexane (10mL). The resulting reaction mixture was refluxed for 16 h at 85 C. After completion of the reaction, the mixture was cooled to room temperature. Then, the pre-cipitate was filtered ,washed with water and dried .Purification by chromatography on silica gel (petroleum ether/ethyl acetate=5/1)afforde dintermediate3.White solid; yield 84%; mp: 201-203C; 1 H NMR (400MHz,DMSO-d 6 ) delta 11.20 (s, 1H), 8.28 (dd, J=8.7, 2.4Hz, 1H), 8.08 (d,J=2.4Hz, 1H), 7.04 (d, J=8.7Hz, 1H), 4.49 (d, J=11.0Hz, 2H),3.55 (d, J=11.2Hz, 2H), 1.34 (s, 3H), 0.84 (s, 3H).

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Shengping; Liu, Yang; Zhang, Zhen; Zhang, Jingya; Zhao, Guisen; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3319 – 3327;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 150544-04-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 150544-04-0 name is 6-Aminoindolin-2-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[00108] To a solution of 6-amino-l ,3-dihydro-indol-2-one (0.15 g, 1.0 mmol) in2:1 CH2Cl2- 1,4-dioxane mixture (30 ml) is added triethylamine (0.30 g, 3.0 mmol) and benzoyl chloride (0.14 g, 1.0 mmol). The reaction is stirred for 2 hours at room temperature, and then a saturated aqueous solution OfNH4Cl is added. The precipitate is collected and washed with water to give crude N-(2-oxo-2,3-dihydro-lH-indol-6-yl)- benzamide. To a solution of this benzamide (20 mg, 0.079 mmol) and lH-rhoyrrole-2- carbaldehyde (7.6 mg, 0.079 mmol) in ethanol (2 ml) is added 2 drops of piperidine. It is EPO stirred at 8O0C for 4 hours and then cooled to room, temperature. The precipitate is collected by vacuum filtration, washed with a small amount of cold ethanol and purified by HPLC (Ci8 column, eluted with CH3CN-H2O containing 0.05percent TFA) to give the desired compound as an orange solid: 1H NMR (DMSOd6) delta 6.34(s, IH)5 6.80 (s, IH), 7.33 (s, IH), 7.39 (d, IH, J = 8.4 Hz), 7.53 (t, 2H, J = 7.8 Hz), 7.57 (s, IH), 7.59 (s, IH), 7.61 (s, IH), 7.64 (s, IH), 7.96 (d, 2H, J = 7.8 Hz), 10.29 (s, IH), 10.94 (s, IH), 13.23 (s, IH); LC-MS: 330.1 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Aminoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; IRM LLC; WO2006/52936; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-79-5, The chemical industry reduces the impact on the environment during synthesis 20870-79-5, name is 5-Nitroindolin-2-one, I believe this compound will play a more active role in future production and life.

Example 67 5-Nitro-indoline (2) A suspension of compound 1 (5 g, 28.1 mmol) in THF (10 mL) was treated with a BH3-THF complex (84 mL, 84 mmol, 1.0 M in THF) and the resulting brown red suspension was refluxed overnight. The reaction was cooled in an ice-bath and methanol (125 mL) was added resulting in orange/red solution which was stirred for half an hour and then concentrated. Methanol (200 mL) was added again and the solution was refluxed for 2 hrs and then concentrated. The residue was subjected to a large silica gel filter with methanol as eluent resulting in a brown solid (2.5 g, 54% yield). 1H-NMR (DMSO-d6) delta 7.90 (dd, J=8.7, 2.4 Hz, 1H), 7.83 (s, 1H), 7.26 (s, 1H), 6.44 (d, J=8.7 Hz, 1H), 3.66 (t, J=9.0 Hz, 2H), 3.04 (t, J=9.0 Hz, 2H).

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, 5-Nitroindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem