Month: February 2021

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. 366453-21-6, name is 4-Hydroxy-2,3-dihydroisoindol-1-one, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 366453-21-6

k Synthesis of 2,3-dihydro-1H-isoindol-1-one (29): To a solution of 4-hydroxy 2,3-dihydro-1H-isoindol-1-one (27) (0.250 gm, 1.67 mmol) in DMF (5 ml) K2CO3 and was added, followed by addition of methyl bromoacetate, and the reaction mixture was stirred at room temperature for 2hr. Then the reaction mixture was then poured on ice and extracted with ethyl acetate (2*15 ml). After the standard workup, the residue was dissolved in methanol (3 ml), and treated with NaOH (5 ml, 1N) at 0 C. and then stirred for and additional hour. After the standard workup, the solid was recrystallized in methanol to give compound 29 (0.140 gm, 60%).

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 366453-21-6.

Reference:
Patent; Jagtap, Prakash; Southan, Garry; Salzman, Andrew; Szabo, Csaba; Ram, Siya; US2002/95044; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, 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 20780-72-7, SDS of cas: 20780-72-7

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2¡¤NH2-H2O ( 35 percent) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-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.

To a suspension of 5-bromoisoindoline-l,3-dione (2.73 g, 12.1 mmol) in THF (20 mL) was added Borane-THF complex (1 M, 48 mL). The reaction was heated at reflux overnight, then cooled to 0 C, and treated with MeOH (30 mL), followed by 2 M HCI (30 mL). The mixture was heated at reflux for 2 h, then cooled to rt and concentrated in vacuo. The residue was partitioned between DCM (50 mL) and H20 (50 mL). The separated aqueous phase was washed with DCM (50 mL x 2), then adjusted to pH 11 with 1 M NaOH (6 mL), and extracted with DCM (80 mL x 4). The combined organic phases were dried over anhydrous a2S04, filtered and concentrated in vacuo to give the crude product as dark brown oil (1.3 g, 54%), which was used in the next step without further purification. MS (ESI, pos. ion) m/z: 198.0 [M + H]+.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 172078-33-0, 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 172078-33-0 as follows.

Compound 2-2: To a solution of 1-chloroisoquinoline-5-sulfonylchloride (0.4 g, 1.53 mmol) in DCM (10 mL) was added TEA (318 muL, 2.29 mmol) and indolin-5-ol (226.9 mg, 1.68 mmol). The mixture was stirred at 25 C. for 12 h under an N2 atmosphere. The reaction mixture was filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 1:1). Compound 2-2, 1-[(1-chloro-5-isoquinolyl) sulfonyl]indolin-5-ol (350 mg, 970.0 mumol, 63.6% yield), was obtained as a yellow solid.

According to the analysis of related databases, 172078-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cervello Therapeutics LLC; Lee, Matthew Randolph; Varano, JR., Anthony Joseph; (53 pag.)US2020/140412; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20870-79-5,Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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.

356 mg of 5-nitro-1,3-dihydro-indol-2-one is hydrogenated in 30 ml of tetrahydrofuran_ethanol=1:1 with 400 mg palladium on carbon (10%) at room temperature and normal pressure for 1 hour. After catalyst is suctioned off on diatomaceous earth and after concentration by evaporation, 320 mg (100% of theory) of 5-amino-1,3-dihydro-indol-2-one is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindolin-2-one, its application will become more common.

Reference:
Patent; Schering AG; US2004/39019; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 60434-13-1, A common heterocyclic compound, 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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 stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

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; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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

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 675109-26-9, 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. 675109-26-9 name is 6-Bromoisoindolin-1-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.

To a mixture of 6-bromoisoindolin-1-one (7.00 g, 3.30 mmol) and 1, 4-dioxane (125 mL), were added bis (pinacolato)diboron (17.00g, 6.60mmol), KOAc (8.50 g, 8.25 mmol) and Pd(dppf)Cl2 (2.50 g, 0.33 mmol). The reaction mixture was stirred at 90 oC for 12h under N2 atmosphere. After cooling to r. t. the reaction mixture was filtered. The solvent evaporated under reduced pressure then added ethyl acetate (80 mL). The precipitate was filtered to obtained black solid. Yield 70%, m.p. > 250oC. 1H NMR (300 MHz, CDCl3) delta (ppm): 8.36 (s, 1H, ArH), 8.00 (d, J = 7.60 Hz, 1H, ArH), 7.48 (d, J = 7.60 Hz, 1H, ArH), 7.03 (s, 1H, NH), 4.48 (s, 2H, CH2), 1.35 (s, 12H, CH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Article; Ji, Dezhong; Zhang, Lingzhi; Zhu, Qihua; Bai, Ying; Wu, Yaoyao; Xu, Yungen; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 334 – 341;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 118289-55-7, These common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-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.

Charged 5- (2-chloroethyl)-6-chloro oxindole (50 GM), 3- (1-PIPERAZINYL)- 1, 2-BENZISOTHIAZOLE (47.5 gm) and cyclohexane (500 mL) into an autoclave. To this sodium carbonate (46 GM), sodium iodide (3.2 GM), tetra butyl phosphonium bromide (14.8 gm) was added and the reaction was maintained at a temperature OF 95-102C and the pressure was kept at 2.5 KG/CM2 TILL the reaction was completed. The reaction mass was cooled to 30C and water (250 mL) was added. The resulting compound was filtered and washed with water (100 mL). The wet compound was further slurred in water (500 mL), filtered and washed with water (100 mL). To the water wet compound was added acetone (500 mL) and was stirred at room temperature for 2 hours and 30 minutes. The solid was filtered, washed with acetone (100 mL) and dried at a TEMPERATURE OF 60-65C to afford the Ziprasidone base (65.7 gm).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES INC.; WO2004/50655; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem