Author: Jessica.F

Synthetic Route of 6326-79-0, A common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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: 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 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; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., COA of Formula: C8H8N2O2

REFERENCE EXAMPLE 6; 5-Amino-1-isopropy.sulfonylindofine; a) 1-isopropy.sulfonyf~5-?itroindoline; 1 mL of TEA (7.61 mmol) and isopropylsulfonyl chloride (0.5 mL, 4.57 mmoi) were added at 0 0C to a solution of 5-nitroindoline (0.5 g, 3.05 mmol) in CH 2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 48 h and then at reflux temperature for 18 h. The crude product obtained was diluted with a saturated aqueous solution of NaHCOs and extracted thrice with CH2Cl2. The combined organic phases were separated, dried over Na2SO4 and the solvent was evaporated to dryness. The desired compound was obtained in quantitative yield and used in next step without further purification.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PALAU PHARMA, S.A.; SALAS SOLANA, Jorge; ALMANSA ROSALES, Carmen; SOLIVA SOLIVA, Robert; FONTES USTRELL, Montserrat; COMELLES ESPUGA, Josep; WO2010/34740; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

7699-18-5, name is 5-Methoxyindolin-2-one, 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. Formula: C9H9NO2

General procedure: 3-(Propan-2-yliden)indolin-2-one (7a): A solution of indolin-2-one (500 mg, 3.76 mmol, 1.0 equiv.) in acetone (15 mL, 0.25 M) was heated in the presence of catalytic amounts of morpholine (164 mL, 164 mg, 1.88 mmol, 0.5 equiv.) for 16 h at reflux temperature. After complete consumption of the indolin-2-one (determined by thin layer chromatography (TLC)) all volatiles were removed under vacuum. Column chromatography(column diameter 5 cm, 30 g silica, v/v (P/EA)6 : 4-1 : 1) afforded the title compound (650 mg, 3.75 mmol, 99 %) as a yellow solid. Apparent multiplets which occur as a result of accidental equality of coupling constants to those of magnetically non-equivalent protons are marked as virtual (virt.). RF 0.70 (P/EA3 : 7; UV). deltaH (CDCl3, 250 MHz,300 K) 7.96 (1H, br s, NH), 7.52 (1H, br d, 3J 7.7, H-4), 7.19(1H, virt. td, 3JE3J 7.7, 4J 1.2, H-6), 7.01 (1H, virt. td, 3JE3J7.7, 4J 1.2, H-5), 6.85 (1H, ddd, 3J 7.7, 4J 1.2, 5J 0.6, H-7), 2.62(3H, s, H-30), 2.39 (3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K)169.5 (s, C-2), 155.7 (s, C-2′), 139.3 (s, C-7a), 127.7 (d, C-6),124.6 (s, C-3), 123.9 (d, C-5), 123.0 (s, C-3a), 121.8 (d, C-4),109.3 (d, C-7), 25.4 (q, C-1′), 23.3 (q, C-3′). The NMR data match the values reported in the literature.[9] 5-Methoxy-3-(propan-2-ylidene)indolin-2-one (7g): Prepared from 5-methoxy-2-oxindole according to RP 1 on a938 mmol scale. The title compound (176 mg, 866 mmol, 92 %) was obtained as a yellow solid. RF 0.45 (P/EA1 : 1; UV). numax(ATR)/cm1 3150w, 3030w, 2938w, 2836w, 1694vs (CO),1619s, 1594w, 1479s, 1305m, 1203w. deltaH (CDCl3, 250 MHz,300 K) 8.07 (1H, s, NH), 7.14 (1H, d, 4J 1.6, H-4), 6.78-6.72(2H, m, H-6/H-7), 3.81 (3H, s, OCH3), 2.62 (3H, s, H-3′), 2.36(3H, s, H-1′). deltaC (CDCl3, 63 MHz, 300 K) 169.8 (s, C-2), 156.0(s, C-3′), 155.2 (s, C-5), 133.4 (s, C-7a), 125.6 (s, C-3a), 123.4 (s,C-3), 111.9 (d, C-4), 111.8 (d, C-6), 109.3 (d, C-7), 56.1 (q,OCH3), 25.3 (q, C-1′), 23.3 (q, C-30). m/z (HRMS ESI)204.1019; [M H)](C12H13NO2) requires 204.1019.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maturi, Mark M.; Poethig, Alexander; Bach, Thorsten; Australian Journal of Chemistry; vol. 68; 11; (2015); p. 1682 – 1692;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 4702-13-0, name is N-Phthaloylglycine, 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 4702-13-0, Product Details of 4702-13-0

Typical Procedure: To a 30-mL vial was added N-phthaloylglycine (2.05 g, 10 mmol) and SOCl2 (8 mL) and the vial was sealed. The reaction was stirred in an oil bath at 60 C for 8 h. The mixture was cooled to r.t., the SOCl2 was removed in vacuo, hexane (10 mL) was added, and the mixture was stirred for 10 min resulting in white solid. After filtration, the solid (2.0 g, 90%) was washed with hexane and used directly in the next reaction. Phthaloylglycyl chloride (2.0 g, 9.0 mmol) in CH2Cl2 (8 mL) was added dropwise to the solution of 11a (2.2 g, 7.9 mmol) and Et3N (3.0 mL) in CH2Cl2 (50 mL). The mixture was stirred at r.t. until completion of the reaction, then diluted with CH2Cl2 (150 mL). The organic phase was washed with H2O (3 ¡Á 40mL) and brine, dried (anhyd Na2SO4), and concentrated in vacuo. The residue was purified by flash column chromatography (silicagel) to afford 10a (3.2 g, 89%) as a yellowish solid.

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; Huang, Liye; Yu, Ruina; Leng, Ling; Gong, Feng; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 17; (2014); p. 2317 – 2326;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

60434-13-1, name is 5-Chloro-1-methylindoline-2,3-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. Safety of 5-Chloro-1-methylindoline-2,3-dione

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

The synthetic route of 60434-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, 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. Quality Control of 4-Bromoisoindoline-1,3-dione

Step b. A mixture of 7-bromo-3-hydroxy-3-methylisoindolin-l-one and 4-bromo-3-hydroxy-3 -methyl isoindolin-l-one (12.00 g, 49.8 mmol) in DCM (100 ml) was cooled to -40¡ãC. Triethylsilane (80.4 ml, 498 mmol) was added to the reaction mixture at -40¡ãC under N2 atmosphere. Boron trifluoride diethyletherate (18.7 ml, 149.4 mmol) was added to the reaction mixture at -40¡ãC under N2 atmosphere. The reaction mixture was stirred at 0¡ãC for 1 h. The resulting reaction mixture was combined with two other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured into NaHC03 solution (500 ml) and extracted with the DCM (3 x 1000 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material obtained was purified by column chromatography (3percent EtOAc in DCM) yielding 7-bromo-3-methylisoindolin-l-one (9.200 g, 40.9 mmol). LCMS: Method A, 1.521 min, MS: ES+ 226.11, 228.11; NMR (400 MHz, CDC13) delta ppm 7.61 (dd, J=7.2, 1.2 Hz, 1 H), 7.43 – 7.38 (m, 3 H), 7.68 – 7.63 (m, 1 H), 1.52 (d, J=6.8 Hz, 3 H).

The synthetic route of 4-Bromoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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. 150560-58-0, name is 5-Isopropylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Isopropylindoline-2,3-dione

General procedure: Isatin based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL¡Á4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

According to the analysis of related databases, 150560-58-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Javid, Muhammad Tariq; Rahim, Fazal; Taha, Muhammad; Nawaz, Mohsan; Wadood, Abdul; Ali, Muhammad; Mosaddik, Ashik; Shah, Syed Adnan Ali; Farooq, Rai Khalid; Bioorganic Chemistry; vol. 79; (2018); p. 323 – 333;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2058-74-4, The chemical industry reduces the impact on the environment during synthesis 2058-74-4, name is 1-Methylisatin, I believe this compound will play a more active role in future production and life.

General procedure: The dicationic ionic liquid 10 (27.03 mg, 10 mol %), was added to a mixture of 1,3-dicarbonyl (1 mmol), isatin (1 mmol), malononitrile (1 mmol), and K2CO3 (13.8 mg, 10 mol %) in water (3 mL). The reaction mixture was stirred at reflux for the appropriate time. After reaction completion (TLC), the reaction mixture was cooled to room temperature and filtered. The filtrate was washed with cool ethanol (3 ¡Á 5 mL) to obtain the corresponding 4H-pyran. The crude products were purified by recrystallization from ethanol (95%). To recover 10, the ethanol/water phase was evaporated under reduced pressure and the crude was washed with ethyl acetate (3 ¡Á 5 mL) and air dried.

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

Reference:
Article; Niknam, Khodabakhsh; Khataminejad, Mohsen; Zeyaei, Fariba; Tetrahedron Letters; vol. 57; 3; (2016); p. 361 – 365;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

As shown in Fig. 133B, a mixture of compound 1 (721 mg, 3.20 mmol, 1.0 eq), compound la (2092) (560 mg, 3.20 mmol, 1.0 eq) and sodium carbonate (866 mg, 8.17 mmol, 2.55 eq) in methanol (10 mL) was stirred at room temperature for 3 h under nitrogen atmosphere. The progress of the reaction mixture was monitored by TLC. After completion of the reaction, the mixture was filtered and the filter cake was washed with methanol and water to afford compound AB17653 (979 mg, 89%) as a red solid. TLC: PE/EA = 3/1, 254 nm; Rf (Compound 1) = 0.6; Rf (Compound AB17653) = 0.4; LC-MS: 338.95 (M-l) ; NMR (400 MHz, d6-DMSO) 511.01 (d, J = 21.5 Hz, 2H), 8.64 (d, J = 8.3 Hz, 1H), 7.62 (d, J = 7.7 Hz, 1H), 7.55 (t, J = 7.6 Hz, 1H), 7.39 (d, J = 8.1 Hz, 1H), 7.18 (d, J = 8.4 Hz, 1H), 7.00 (dd, J = 8.8, 4.6 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, 6-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EINZIGER, Michael; SIMPSON, Ann, Marie; (499 pag.)WO2019/200232; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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.

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5- bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -78C under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -78C for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia / DCM gave 111 mg of 5-(4-hydroxy-1-methyl- piperidin-4-yl)-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester as a colourless oil.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem