Month: November 2020

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.

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 hours, and then heated to 30 C for 3 hours. To the solution, was added HCI (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hour. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSOd5) delta 7.69 (brs, IH, NHH), 7.74 (t, J= 8 Hz, IH, Ar), 7.92 (dd, J = 1, 8 Hz, IH, Ar), 8.13 (dd, /= 1, 8 Hz, IH, Ar), 8.15 (brs, IH, NHH), 13.59 (s, 1eta, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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

Reference:
Patent; CELGENE CORPORATION; WO2008/39489; (2008); A2;,
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Indoline | C8H9N – PubChem

32372-82-0, 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. 32372-82-0, name is Isoindoline hydrochloride, A new synthetic method of this compound is introduced below.

Manganese dioxide (2.80 g, 24.0 mol, 10 eq.) was added to a solution of 93 (550 mg, 2.40 mmol, 1 eq.) in dichloromethane (120 mL) at room temperature. The resulting mixture was stirred at room temperature for 16 h, filtered through a small pad of celite, eluted with ethyl acetate, and concentrated. Solvent was removed to give the corresponding aldehyde, which was used further as obtained. Lithium hydroxide monohydrate (1.02 g, 24.0 mmol) was added to a solution of the aldehyde in methanol (8 mL), tetrahydrofuran (8 mL), and water (8 mL). The resulting mixture was stirred for 14 h at room temperature. The residue was treated with 1 M hydrochloric acid and the pH was adjusted to 2. The resulting suspension was extracted with ethyl acetate (3chi50 mL), and the combined organic layers were washed with saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford the corresponding acid as an off-white solid which was used further as obtained. 1-Ethyl- 3-(3- dimethylaminopropyl)carbodiimide (1.53 g, 4.80 mmol) was added to a stirred solution of the acid, isoindoline hydrochloride (485 mg, 3.12 mmol), 1-hydroxybenzotriazole (735 mg, 4.8 mmol), N,N-diisopropylethylamine (1.25 mL, 7.20 mmol) in dichloromethane (24 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with a saturated sodium bicarbonate solution (20 mL). The organic layer was washed with 1 M hydrochloric acid solution (15 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :3 hexanes/ethyl acetate) to afford 94 as a light brown amorphous solid (331 mg, 43%). HRMS (ESI+) m/z [M + H+] calc. for C20H2oN03, 322.1443, found 322.1449.

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; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-2,3-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 324-03-8, 324-03-8

General procedure: Compound 2h was prepared from 6-fluoro-1H-indole-2,3-dione 1f and dl-leucine in a similar manner to that described for the synthesis of compound 2a and obtained in 64% yield as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 0.86-0.91 (m, 6H), 1.31-1.45 (m, 2H), 1.61-1.69 (m, 1H), 1.79-1.89 (m, 1H), 2.16-2.23 (m, 1H), 2.93-2.96 (m, 1H), 3.12 (s, 3H), 3.28-3.32 (m, 1H), 3.42-3.53 (m, 1H), 6.55-6.61 (m, 1H), 6.66-6.74 (m, 1H), 7.01-7.09 (m, 1H), 10.45 (s, 1H). MS m/z 321 (M+H)+.

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, 6-Fluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article in Press; Ito, Masahiro; Iwatani, Misa; Yamamoto, Takeshi; Tanaka, Toshio; Kawamoto, Tomohiro; Morishita, Daisuke; Nakanishi, Atsushi; Maezaki, Hironobu; Bioorganic and Medicinal Chemistry; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 317-20-4, name is 7-Fluoroisatin, 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. 317-20-4

General procedure: The mixture of substituted isatins 1 (1 mmol), phthalic anhydride or succinic anhydride 2 (1 mmol), 1,3-dimethylurea (1,3-diethylurea) 3 (1.5 mmol), p-TSA?H2O (0.2 mmol), and CH3CN (3 mL) was put in a 25 mL flask and reacted under 80 C (monitored by TLC) about 5 h. After completion, the reaction the mixture was cooled to room temperature and the precipitate was obtained by filtration. Compound 4 was purified by recrystallization from EtOH.

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, 317-20-4, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Lei; Xu, Hui; Yan, Lirong; Xu, Zhongyun; Ling, Zhi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron Letters; vol. 58; 25; (2017); p. 2468 – 2474;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6326-79-0, name is 6-Bromoisatin, 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. 6326-79-0

To a solution of compound 9 (10 g, 44.44 mmol) in EtOH (130 mL) was added a solution of hydroxylamine hydrochloride (4.61 g, 66.37 mmol) in H2O (20 mL), and the mixture was stirred at 80 C. for 12 h. The mixture was concentrated under reduced pressure and the solid formed was filtered, washed with cold water, and dried under high vacuum to afford 10.24 g (96%) of compound 10 as a blood-red solid. IR (KBr) numax. cm-1: 3336, 3330 (NH2), 3310 (OH), 3038 (Ar-H), 2920 (Alph-H), 1690 (C?O), 1612, 1515, 1414 (C?C), 1260 (C-N). 1H NMR (500 MHz, DMSO-d6) delta=7.02 (s, 1H, H-7); 7.20 (d, 1H, J=8.2 Hz, H-5); 7.84 (d, 1H, J=8.1 Hz, H-4); 10.83 (s, 1H, NH); 13.49 (s, 1H, OH); 13C NMR (125.7 MHz, DMSO-d6) delta=113.12 (aromatic-C), 115.50 (aromatic-C), 124.84 (aromatic-C), 128.46 (aromatic-C), 143.48 (aromatic-C), 144.02 (aromatic-C), 164.29, 167.12 (C?O). Calculated (%) for C8H5BrN2O2(239.95); C, 39.86; H, 2.09; N, 11.62. found (%); C, 39.80; H, 2.14; N, 11.58.

Statistics shows that 6326-79-0 is playing an increasingly important role. we look forward to future research findings about 6-Bromoisatin.

Reference:
Patent; King Fahd University of Petroleum and Minerals; King Abdulaziz City for Science and Technology; Ullah, Nisar; US8916704; (2014); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

317-20-4, 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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows.

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 C (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.

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

480-91-1, A common compound: 480-91-1, name is Isoindolin-1-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.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

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, Isoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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 675109-26-9 as follows. 675109-26-9

Preparation 42: 6-bromo-2-[(3-methyloxetan-3-yl)methyl]-2,3-dihydro-1 H-isoindol-1 -one (1538) (1539) A stirred suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (300 mg, 1.42 mmol) in DMF (4 mL) was cooled in an ice-bath and treated with sodium hydride (60% dispersion in mineral oil, 68 mg, 1.70 mmol) and stirred and cooled for 15 min. The mixture was treated with 3- (bromomethyl)-3-methyloxetane (280 mg, 1.70 mmol) and stirred at RT for 18 h. Brine (20 mL) was added and the crude product was extracted with ethyl acetate (2x 20 mL). The combined extracts were washed with brine (20 mL), dried (MgS04) and evaporated. The residue was purified by chromatography (S1O2, 20-100% ethyl acetate in /so-hexane) to afford the title compound (342 mg, 81 %) as a yellow solid. LC-MS: [M+H]+ = 296/ 298.

According to the analysis of related databases, 675109-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 99365-40-9, name is 6-Bromoindolin-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. 99365-40-9

To a suspension of potassium tert-butylate (12.8 g) in dry THF (80 ml) was added portion wise at 0 C 6-bromoindolin-2-one (5.0 g,) followed by copper (I) bromide-dimethylsulfide complex(470 mg). Mel (6.82 g) was added drop wise within 45 mm keeping the internal temperature below 8 C, the mixture was warmed to 22 C and stirring was continued for 16 hours. The mixture was quenched at 0 C with saturated aqueous ammonium chloride solution and diluted with TBME and water. The organic layer was dried, evaporated and the residue purified by flash chromatography (silica gel, EtOAc/ n-heptane, 1:1) to give the title compound (5.17 g) as abrown solid (5.17 g, 9 1%). MS (mlz): 240.4/ 242.4 [(M+H)?i.

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, 99365-40-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 99365-40-9 name is 6-Bromoindolin-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. 99365-40-9

Commercially available 6-bromoxindole (656 mg), zinc cyanide (288 mg) and tetrakis triphenylphosphine palladium(0) (175 mg) were suspended in dry N,N-dimethylformamide (6 mL). The resulting mixture was degassed by three pump/vent cycles with argon and then placed in a preheated oil bath (80 C.). After stirring at this temperature for 15 h the mixture was cooled to room temperature, diluted with water (60 mL) and extracted with ethyl acetate (3¡Á60 mL). The combined organic layers were washed with water (2¡Á60 mL), dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, dichloromethane/methanol) to afford the title compound (385 mg; 81%). [MH]+=159.

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

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem