Month: March 2021

Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, 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 7147-90-2, SDS of cas: 7147-90-2

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added benzylmagnesium chloride (2 M in THF, 30 mL) dropwise at 0 C. After the addition, the reaction mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regio isomers (5.47 g, 100%). MS: 274.1 (M+H+).; Under N2 protection, triethylsilane (23 g, 200 mmol) and TFA (10 mL) were added successively to a mixture of 3-benzyl-5-chloro-3-hydroxy-2,3-dihydro-isoindol-l-one and 3-benzyl-6-chloro-3-hydroxy-2,3-dihydro-isoindol-l-one (5.47 g, 20 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. NaHC03 solution (30 mL) and extracted with DCM (2 x 30 mL). The combined organic layers were washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude mixture of products. The desired regioisomer, 3-benzyl-5-chloro-2,3-dihydro-isoindol- 1 -one was obtained by prep- HPLC separation as a white solid (1.03 g, 20%). MS: 258.1 (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; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
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Application of 6872-06-6, 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. 6872-06-6 name is 2-Methylindoline, 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.

Under the protection of anhydrous oxygen-free and inert gas, 0.01161 g (1.14¡Á10-5 mol) {L1La[N(SiMe3)2]}2 was added to the reaction flask, and then 148 muL (1.14¡Á10-3 mol) 2- Methyl porphyrin was added to 1.41 mL of tetrahydrofuran and stirred at room temperature for 0.5 hour. Further, 0.34 mL (3.40 x 10-3 mol) of benzaldehyde was added, and after the reaction was stirred for 3 hours, the reaction was completed.Pour the reaction solution into an eggplant-shaped bottle, add a small amount of ethyl acetate to the reaction flask and wash it three times, still pour into the eggplant-shaped bottle.Add appropriate amount of silica gel, spin dry, and then load on the packed column of silica gel.The column was passed through a suitable eluent (ethyl acetate: petroleum ether = 1: 6) to afford product, yield 75%.

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

Reference:
Patent; Soochow University (Suzhou); Zhao Bei; Xiao Yang; Lu Chengrong; (18 pag.)CN104817583; (2019); B;,
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.

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dirnethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1 H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1 H, s), 10.32 (1H, s), 7.36 (1H, br.s), 7.35 (1 H1 s), 7.28 (3H, br.s), 6.59 (1H1 s), 4.77 (2H1 br.s), 4.71 (2H1 br.s). MS: [M+H]+ 332/334.

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; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); A1;,
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Application of 7699-18-5, The chemical industry reduces the impact on the environment during synthesis 7699-18-5, name is 5-Methoxyindolin-2-one, I believe this compound will play a more active role in future production and life.

PREPARATION A N-methyl-5-methoxyoxindole 5-methoxy oxindole (450 mg, 2.76 mmol) and potassium carbonate (585 mg, 4.23 mmol) were combined in 45 ml of acetone under an inert atmosphere. To this white, heterogenous mixture was added 0.33 ml of methyl iodide (5.30 mmol) via syringe. The reaction mixture was stirred at room temperature for 10 hours and then at 75 C. for 3 hours. Additional potassium carbonate and methyl iodide were added (290 mg and 0.11 ml, respectively), and the reaction mixture was stirred at 75 C. for 6 more hours. The reaction mixture was then poured into 300 ml of saturated brine solution and extracted with 3*200 ml ether. The combined organic layers were dried over MgSO4, filtered, and stripped to a yellow oil. This was purified via flash chromatography (3:1 ethyl ether/hexane) to provide the title compound (307 mg, 63% yield) as white crystals: m.p. 93-94 C. M/z calculated for C10 H11 NO2: 177.0790, Found: 177.08066.

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

Reference:
Patent; Pfizer Inc.; US5502072; (1996); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 603-62-3, 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. 603-62-3, name is 3-Nitrophthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1; Preparation of (2-methyl-l,3-dioxo-2,3-dihydro-lH-isoindol-4-yl)acetic acid; Step 1 : 4-Amino-l,3-isoindolinedione; A solution of 3-nitrophthalimide in ethylacetate was treated with 10% palladium on charcoal (10 wt. %) and hydrogenated at 20 psi for 2h. The catalyst was filtered through celite and the filterate was evaporated to give the crude product (97%) which was used without purification in the next step. 1H-NMR (delta ppm, DMSO-J6, 300 MHz): 10.85 (br. s, IH); 7.39 (t, J = 7.8, IH); 6.93 (d, J = 8.4, IH); 6.88 (d, J = 6.9); 6.38 (br. s, 2H).

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

Reference:
Patent; GLENMARK PHARMACEUTICALS, S. A.; WO2009/118596; (2009); A2;,
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. 611-09-6, name is 5-Nitroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Safety of 5-Nitroindoline-2,3-dione

General procedure: A mixture of an isatin (1mmol), molononitrile (1mmol), CH activatedacid (1mmol), and [C4(DABCO)2]¡¤2OH(2mol%) inwater (3mL)was stirred at 80 C. The reaction progress was monitored by TLC [eluent:n-hexane:EtOAc (9:2)] (It is important to that by beginning of thereaction the products were precipitated in the reaction medium).After completion of the reaction, the mixture was cooled to room temperature and the solid product was filtered, washed with cold distilledwater (2 mL) to obtain essentially pure products. The solid productswere recrystallized from ethanol if necessary.

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

Reference:
Article; Goli-Jolodar, Omid; Shirini, Farhad; Seddighi, Mohadeseh; Journal of Molecular Liquids; vol. 224; (2016); p. 1092 – 1101;,
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 7223-50-9 as follows. Recommanded Product: N-Propargylphthalimide

AgNO3 (36.1 mg, 0.21 mmol) and N-bromosuccinimide (576 mg, 3.24mmol) were added to a solution of 2-(prop-2-yn-1-yl)isoindoline-1,3-dione (2a; 371 mg, 2.00 mmol) in acetone (2.0 mL). The reactionmixture was stirred at r.t. for 16 h. Afterwards, the mixture waspoured on ice and extracted with EtOAc. The combined organic layerswere dried (anhyd Na2SO4), concentrated, and the crude product waspurified by flash chromatography (silica gel, PE/EtOAc 8:2). Bromoalkyne3a was isolated as a white solid; yield: 495 mg (1.87 mmol,94%); mp 119-120 C; Rf = 0.35 (PE/EtOAc 7:3).

According to the analysis of related databases, 7223-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kohr, Michael; Kazmaier, Uli; Synthesis; vol. 50; 23; (2018); p. 4690 – 4694;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7477-63-6,Some common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, molecular formula is C8H4ClNO2, 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: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, 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 868066-91-5, Recommanded Product: 5-Bromo-2-methylisoindolin-1-one

General procedure: Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solution of 2 M Na2CO3 (3 mL) and Pd(dppf)C12 (94 mg, 0.12 mmol) were added and the entire mixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30 mmol) was added and reflux continued under N2 overnight. Upon cooling, themixture was diluted with water (100 mL) and extracted with CH2C12 (6×50 mL). The combined organic fractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure to give a crude solid which was purified by flash column chromatography on silica gel (EtOAc as eluant). The title compound was isolated as a light-brown solid (510 mg, 97percent). ?H NMR [400 MHz, (CD3)2S0] 8 7.87 (s, 1 H), 7.77 (dd, J? 7.9, 1.6 Hz,1 H), 7.67 (dd, J 7.9, 0.3 Hz, 1 H), 7.61-7.66 (m, 2 H), 7.18 (dd, J 5.0, 1.4 Hz, 1 H),4.49 (s, 2 H), 3.08 (s, 3 H). LRMS (APCI) calcd for C13H,2NOS 230 (MH), found 230.

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; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7699-18-5, name is 5-Methoxyindolin-2-one, 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 7699-18-5, SDS of cas: 7699-18-5

General procedure: 4.4.2 (Z)-5-methoxy-3-((2-(4-methoxyphenyl)-1H-benzo[d]imidazol-6-yl)methylene)indolin-2-one (5b) Compound 5b was prepared according to the method described for compound 5a, employing aldehyde 11a (126 mg, 0.5 mmol) and 5-methoxyindolin-2-one (12b, 81 mg, 0.5 mmol) to obtain the pure product 5c as a yellow solid (114 mg, 58%); mp: 177-179 C; IR (KBr): 3422, 3153, 2931, 2352, 1681, 1642, 1576, 1474, 1435, 1254, 1179, 1029, 961, 864 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 10.41 (bs, 1H), 8.25-8.16 (m, 3H), 7.82 (s, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.58 (d, J = 8.3 Hz, 1H), 7.40 (s, 1H), 7.12 (d, J = 8.6 Hz, 2H), 6.82-6.70 (m, 2H), 3.90 (s, 3H), 3.68 (s, 3H); 13C NMR (75 MHz, DMSO-d6): delta 168.9, 160.6, 154.3, 153.7, 153.1, 137.4, 136.2, 128.0, 127.9, 127.6, 126.1, 124.5, 123.7, 122.0, 121.9, 113.9, 109.9, 108.5, 55.0; MS (ESI): m/z 398 [M + H]+; HRMS (ESI): calcd for C24H20O3N3 m/z 398.14923 [M + H]+; found 398.14992.

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; Kamal, Ahmed; Nagaseshadri; Nayak, V. Lakshma; Srinivasulu, Vunnam; Sathish, Manda; Kapure, Jeevak Sopanrao; Suresh Reddy; Bioorganic Chemistry; vol. 63; (2015); p. 72 – 84;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem