Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, 317-20-4

In a 25 ml round bottom flask were added N, N’-dibutyl-2-nitroethylene-1,1-diamine (1 mmol) and 7-Indoline-2,3-dione (1.1 mmol), toluene (15 ml) and acetic acid (1 mmol) were added under heating with magnetic stirringTo 110 C for 14 hours. The reaction was monitored by TLC, until the point of complete disappearance of raw materials, the reaction was added 50 ml of acetic acidEster and 50 ml of a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous Na 2 SO 4. The dried organicThe phase was concentrated to dryness decompression pressure, after adding 3 ml of concentrated dry distillate acetone and 4 grams of 100 ~ 200 mesh silica gel Stirred byDrying under pressure, loading the sample, separating and drying on a silica gel column using a petroleum ether / ethyl acetate = 7: 1 eluent to obtain a red solid product N-butyl-2- (Butylamino) -7-fluoro-3-nitroquinoline-4-carboxamide (Compound 32) in 90% yield.

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

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); 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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., 3484-35-3

General procedure: To a mixture of oxindole (3a-f, 0.3mmol), 1-alkyl-1H benzo[d]imidazole-2-carbaldehydes (7a-e, 0.33mmol) in ethanol (2mL), was added catalytic amount of piperidine. The reaction mixture was stirred at reflux until complete consumption of the oxindole observed by TLC. After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-ones 8a-z orange/yellow solids in moderate to good yields. Compounds 8c, 8f, 8i, 8l and 8o did not precipitated out from ethanol, were purified by column chromatography with silica gel (60-120) by using ethyl acetate:hexane (2:8 to 3:7). 4.1.1.14 (E)-3-((1-Ethyl-1H-benzo[d]imidazol-2-yl)methylene)-5-methylindolin-2-one (8n) Orange solid, Yield 84%; mp: 274-276 C; FT-IR: (cm-1): 3166, 3067, 2980, 1704, 1615, 1323, 813, 742;1H NMR (300 MHz, DMSO-d6): delta 10.20 (brs, 1H, NH), 9.22 (s, 1H, Ar-H), 7.87 (d, J = 7.2 Hz, 1H, Ar-H), 7.65-7.58 (m, 1H, Ar-H), 7.56 (s, 1H, C=CH), 7.51-7.28 (m, 2H, Ar-H), 7.09 (d, J = 7.9 Hz, 1H, Ar-H), 6.78 (d, J = 7.9 Hz, 1H, Ar-H), 4.54-4.41 (m, 2H, CH2), 2.38 (s, 3H, CH3), 1.50 (t, J = 7.3 Hz, 3H, CH3); 13C NMR (125 MHz, DMSO-d6): delta 168.9, 146.8, 142.9, 141.3, 134.6, 131.7, 131.2, 129.9, 128.6, 124.1, 122.9, 121.1, 119.8, 117.1, 110.6, 109.3, 38.4, 21.0, 15.7; HRMS (ESI): m/z calcd for C19H18N3O 304.1450, found 304.1438 [M+H]+; Purity: 98.7%.

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:
Article; Sharma, Pankaj; Thummuri, Dinesh; Reddy, T. Srinivasa; Senwar, Kishna Ram; Naidu; Srinivasulu, Gannoju; Bharghava, Suresh K.; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 584 – 600;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

52351-75-4, The chemical industry reduces the impact on the environment during synthesis 52351-75-4, name is 6-Methoxyindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

5.0 g (1 equivalent) of 6-methoxyisatin was dissolved in 25 ml of ethanol.Add 4 ml (1.1 equivalents) of acetophenone and 5.2 g (3 equivalents) of potassium hydroxide solid, heat at 80 C under reflux, and stir for 48 hours.The heating and stirring were stopped, the ethanol was concentrated to dryness, and extracted with ethyl acetate and water three times. The organic phase was combined, and the organic phase was concentrated by spin-drying, and then neutralized by adding 2N diluted hydrochloric acid in an ice bath to precipitate a solid. After the test paper was detected to be weakly acidic, the acid was stopped to be added dropwise, and the mixture was allowed to stand for filtration, and the filter cake was washed with water to obtain 6.20 g of a pale red solid. The yield was 74%.

The chemical industry reduces the impact on the environment during synthesis 6-Methoxyindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sun Yat-sen University; Wang Yuanxiang; Zhang Xiaolei; Huang Qiuyao; Zhong Yan; Hu Wenhao; (26 pag.)CN110105279; (2019); A;,
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 71294-03-6 as follows. 71294-03-6

Example 9 Preparation of 3-(4,6-diethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one 7-Fluoro-1,3-dihydro-2H-indol-2-one (1.0 g) is introduced as initial charge in 10 ml of N,N-dimethylacetamide. A solution of potassium carbonate (1.8 g) and potassium hydroxide (0.3 g) in 10 ml of water is added and the mixture is briefly after-stirred. Then, a solution of 2-chloro-4,6-diethoxy-1,3,5-triazine (3.0 g, ca. 50% purity) in 10 ml of N,N-dimethylacetamide, and 10 ml of water are added. A solid separates out from the clear yellow solution. The mixture is stirred at room temperature and further 2-chloro-4,6-diethoxy-1,3,5-triazine (1 g, ca. 50% purity) is added in two portions after 2 and 18 hours. The mixture is stirred for a further 3 hours at 30 C., admixed with 10 ml of toluene, adjusted to pH 1-2 with hydrochloric acid (10%) and after-stirred for 30 min. The solid is filtered off with suction, washed twice alternately with water and heptane and dried. This gives the title compound as solid in an HPLC purity of 99% area (1.53 g, 72% of theory). LC-MS: M+H=319 (86%). 1H NMR (400 MHz, DMSO-D6): delta (ppm)=11.3 (s, 1H), 7.59 (d, 1H), 6.96 (dd, 1H), 6.93-7.00 (m, 1H), 4.50 (q, 4H), 1.37 (t, 6H).

According to the analysis of related databases, 71294-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Karig, Gunter; Ford, Mark James; Siegel, Konrad; US2013/345422; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-74-4,Some common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, molecular formula is C9H7NO2, 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 N-methylisatin (322 mg, 2.0 mmol), phenylacethylene (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 soild, 347 mg (66%).

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

Reference:
Article; Roh, Hwa Jung; Kim, Su Yeon; Min, Beom Kyu; Kim, Jae Nyoung; Tetrahedron Letters; vol. 58; 1; (2017); p. 21 – 24;,
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

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

3484-35-3, Name is 5-Methylindolin-2-one, 3484-35-3, 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.

General procedure: To a solution of appropriate oxindole (8a-e, 0.3 mmol) in ethanol (3 mL) was addedcorresponding aldehyde (12a-h, 0.32 mmol) and a catalytic amount of piperidine. The reactionmixture was stirred at reflux for 6-12 h (monitored by TLC). After cooling, the precipitate wasfiltered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(4′-(aminoalkoxy)-3′-methoxybenzylidene)indolin-2-one title compounds of formula (5a-t) as yellow/brown/orangesolids in moderate to excellent yields.

Statistics shows that 5-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 3484-35-3.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C ? H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60¡ãC for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.

The synthetic route of 7-Methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Wei-Hong; Chen, Meng-Nan; Hao, Yi; Jiang, Xin; Zhou, Xiao-Lin; Zhang, Zhan-Hui; Journal of Molecular Liquids; vol. 278; (2019); p. 124 – 129;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

61-70-1, Adding some certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-2-one, 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 61-70-1.

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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 61-70-1.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

71294-03-6, A common compound: 71294-03-6, name is 7-Fluoroindolin-2-one, 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.

a) 7-fluoro-1,3,3-trimethylindolin-2-one To a suspension of NaH (8.79 g, 220 mmol) in tetrahydrofuran (100 ml) was added 7- fluoroindolin-2-one (8.30 g, 54.9 mmol) portionwise within 20 minutes. The reaction mixture was stirred for 30 minutes. Mel (31.2 g, 13.7 ml, 220 mmol) was added dropwise at 24-27 Cwithin 1.5 hours. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was very carefully quenched with 20 ml saturated aqueous ammonium chloride solution at 10-15 C, then diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gelchromatography using ethyl acetate heptane as eluent. The title compound was obtained as orange crystals (9.91 g).MS ESI (mz): 194.3 [(M+H)j.1H NMR (CDC13, 400 MHz): 8(ppm) = 6.99-6.97 (m, 3H), 3.43 (d, J = 2.62 Hz, 3H), 1.37 (s, 6H).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem