Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 1677-48-1, name is 5,6-Dichloroindoline-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 1677-48-1, Recommanded Product: 5,6-Dichloroindoline-2,3-dione

General procedure: A mixture of 4-(chlorobenzyloxy)benzoylhydrazines (0.01 mol) and 4,5-dichloroindolin-2,3-diones (0.01 mol) in ethanol (70 ml) containing 3-4 drops of glacial acetic acid was refluxed for 1-2 hr and left overnight at room temperature. The solid product so obtained was filtered, washed with methanol and recrystallised from aq. DMF. Compounds 1b-5b were synthesized using same method and gave satisfactory analysis for C, H and N.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Dichloroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur; Indian Journal of Heterocyclic Chemistry; vol. 23; 4; (2014); p. 411 – 418;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-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. Safety of 5-Bromoisoindolin-1-one

5-bromoisoindolin-1-one (1.00 g; 4.63 mmol; 1.00 eq) dissolved in a mixture of THF (25.00 ml) and DMF (4.50 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 185 mg; 4.62 mmol; 1.00 eq) and tetrabutylammonium iodide (349.0 mg; 0.92 mmol; 0.20 eq) in THF (23.00 ml). After 1.5 h stirring at rt, 4-methoxybenzyl chloride (724.0 mg; 4.63 mmol; 1.00 eq) was added and the mixture was stirred 18h at rt. The reaction mixture was used in the next step without work-up.

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 3-OBoc-oxindoles 3a and 3e-g were synthesized by following our earlier reportedproceudure.1 In a 100ml round bottom flask was charged with 1g of N-protected isatin, 1equivalent of CeCl3.7H2O and the mixture was dissolved by methanol (2mL/mmol) then0.5equivalent of NaBH4 was added portion wise at 0 C. After addition of NaBH4 the reactionmixture was quenched imidiately by excess of ice and taken extract with ethylacetate twice. Theorganic fractions was combined and dried over anhydrous Na2SO4 and evaporated through rotary vacuum.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jayakumar, Samydurai; Kumarswamyreddy, Nandarapu; Prakash, Muthuraj; Kesavan, Venkitasamy; Organic Letters; vol. 17; 5; (2015); p. 1066 – 1069;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

(B) 15gm (0.0617mole) 4-phthalimido cyclohexanone was dissolve in 150ml Ethylacetate. Cool the mass to 0C. Add Br2 solution (9.8gm Bra in 25ml of methanol) and0.25gm of Aids under stirring. Stop stirring and allow initiating bromination and findingclear solution then add remaining quantity of Br2 solution and stir for 10-15mins. Washthe reaction mass with 75ml 2% NaS2O3 solution then wash organic phase with 75ml8%NaHCO3. Then in last wash it with brine solution. Collect organic masses andevaporate it under vacuum. Dry it at 50C for 2-3hrs.YIELD: 15gms(75.2%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ALEMBIC LIMITED; WO2006/3677; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3339-73-9,Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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.

EDCHCI (2.8 g, 15.0 mmol) was added to a solution of 3-(1,3-dioxoisoindolin-2-yl)propanoic acid (2.2 g, 10.0 mmol) in THF (30 mL followed by HOBt (1.84 g, 12.0 mmol) and the reaction mixture was stirred for 20 mm at room temperature. 2-methoxyacetohydrazide (1.05 g, 10.0 mmol) was added to the reaction mixture followed by DIPEA (6.4 g, 50.0 mmol) and thereaction mixture was stirred at room temperature for 16 h. Volatiles were removed under reduced pressure and the reaction mixture was diluted with water (30 mL). The aq. layer wasextracted with DCM (3 x 25 mL), combined organic layer was washed with aqueous NaHCO3 solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the product (2.0 g, 65 %) as white solid. ?H NIvIR (400 MHz, DMSO-d6): 6 9.91 (s, 1H), 9.72 (s, IH), 7.88-7.82 (m, 4H), 3.88 (s, 2H), 3.78 (t, J= 7.6 Hz, 2H), 3.30 (s, 3H), 2.25 (t, J?7.6 Hz, 2H); LC-MS: [M+Hj = 306.3 mlz.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (89 pag.)WO2016/105477; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. COA of Formula: C8H4BrNO2

5-bromoisoindole-1,3-dione (10 g, 44.2 mmol) was added to THF (50 mL). The temperature was raised to 80 C, stirred for 24 h, ice water bath, methanol (30 mL) was added dropwise, 3N hydrochloric acid (30 mL), refluxed for 4 h, concentrated, diluted with water (100 mL), then washed with diethyl ether (50 mL ¡Á 2), water phase The mixture was adjusted to pH = 10 with saturated aqueous sodium carbonate, and extracted with EA (50mL¡Á2), dried and concentrated to give 5.7 g (64.1%) of yellow oil.

The synthetic route of 5-Bromoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Liu Zhanzhu; Shen Zhufang; Sun Zhaozhu; Pan Xuan; Zhou Tian; Huan Yi; Guan Baohe; (76 pag.)CN110294744; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3783-77-5, The chemical industry reduces the impact on the environment during synthesis 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

To a solution of tert-butyl [(2R)-l-(aminooxy)-3-methylbutan-2-yl]carbamate (5.0 gm, 23.04 mmol) in pyridine (50 ml) was added N-(3-oxo-butyl)-pthalamide (5.0 gm, 23.04 mmol) under stirring at 30C. The reaction mixture was stirred at 30C for 12 hours. After completion of the reaction, solvent was evaporated under vacuum and the residue obtained was dissolved in ethyl acetate (200 ml). The ethyl acetate layer was washed with saturated aqueous ammonium chloride solution, water and brine solution. Layers were separated and organic layer was dried over sodium sulphate. Evaporation of solvent provided crude mass, which was purified by triturating with diethyl ether to provide 6.1 gm of 2-[(3E/Z)-3-({ [(2R)- 2-(tert-butoxycarbonyl)amino-3-methylbutyl]oxy}imino)butyl]-lH-isoindole-l,3(2H)-dione as a colourless oil (63% yield). Analysis: Mass (M+l): ES: 418.3 for C22H31N3O5; 1H NMR (400 MHz, CDC13): delta 7.83-7.88 (m, 2H), 7.70-7.73 (m, 2H), 4.67-4.70 (br s, 1H), 3.84-3.98 (m, 2H), 2.65-2.89 (m, 2H), 2.53 (ddd, 1H), 1.91 (d, 3H), 1.70-1.77 (m, 1H), 1.43 (s, 9H), 0.84-0.90 (m, 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, 2-(3-Oxobutyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WOCKHARDT LIMITED; CHAVAN, Vijay Prakash; BHAVSAR, Satish; PAVASE, Laxmikant; GUPTA, Sunil; MISHRA, Amit; KALE, Rajesh; JOSHI, Sanjeev; DABHADE, Sanjay Kisan; JADHAV, Sunil Bhaginath; KAYASTHA, Abhijeet Kantilal; PAWAR, Shivaji Sampatrao; RANE, Vipul Prabhakar; AHIRRAO, Vinod Kashinath; YEOLE, Ravindra Dattatraya; DESHPANDE, Prasad Keshav; BHAGWAT, Sachin Subhash; PATEL, Mahesh Vithalbhai; (50 pag.)WO2018/203197; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 118289-55-7,Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

500 g of 3-(1-piperazinyl)-1,2-benzisothiazole hydrochloride of the formula I compound was added to 5 L of acetonitrile, then 422 g of potassium carbonate was added, and after stirring for 30 minutes, 450 g of 5-(2-chloroethyl)-6-chloro-1,3-dihydro-fluorenone was subsequently added thereto and 10 g of sodium iodide, heated to reflux, and warmed to completion. The solvent was removed under reduced pressure. 2L of deionized water was added and the mixture was stirred for 2 hours. The filter cake was rinsed with 500 ml of deionized water, and the filter cake was dried to obtain crude ziprasidone IV767g in a yield of 95.1%. The crude product was 99.5% pure and 1,4-bis(benzo[d]isothiazole-3- The base) piperazine (VI) has a content of less than 0.05%, and this reaction is carried out by commercially available formula I to obtain ziprasidone IV of the type having a yield of 90% and a purity of 98.8%, wherein 1,4-bis(benzo[d]isothiazol-3-yl)piperazine The content of formula (VI) is more than 0.15%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Chloro-5-(2-chloroethyl)indolin-2-one, its application will become more common.

Reference:
Patent; Shanghai Tianci Biological Gu Biological Engineering Co., Ltd.; Li Xinjuanzi; Li Jianzhi; Wang Xun; Li Yonggang; Shen Xiaoliang; Gao Yan; Lv Xinghong; (14 pag.)CN104370850; (2018); B;,
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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromoisoindoline-1,3-dione

A mixture of 4-bromophthalic anhydride (25 g) in formamide (75 ml) was heated at 2000C for 16 hours then allowed to cool to room temperature. The reaction mixture was diluted with water (200 ml), filtered, the filter cake was washed with water then diethyl ether and sucked dry to give 20.85 g of light mustard solid.280 ml of 1 M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at O0C then heated at reflux overnight. The reaction was cooled to 00C then treated cautiously with methanol (100 ml) followed by 2M HCI (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (x3). The aqueous was basified with 2M NaOH then extracted with DCM (x3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1 H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1H, s), 7.36 (1 H, d), 7.20 (1H, d), 4.05 (4H, s).

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 6941-75-9.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44029; (2008); A1;,
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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Safety of 2-(Bromomethyl)isoindoline-1,3-dione

(12b) To a solution of the malonate (1.0 g, 4.0 mmol) from reaction (12a) in N,N-dimethylformamide (8 mL) was added at 0 C. sodium hydride (60% dispersion in mineral oil, 0.34 g, 2.1 eq). After 20 min, N-(bromomethyl)phthalimide (1.0 g, 1.04 eq) was added. The reaction mixture was stirred at 0 C. for 1 h before quenched with aqueous ammonium chloride, and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4), concentrated and purified by silica gel chromatography (20% then 40% ethyl acetate/hexane) to provide the desired alkylated product (0.9 g, 55%).

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; Duan, Jingwu; Jiang, Bin; Chen, Lihua; Lu, Zhonghui; Barbosa, Joseph; Pitts, William J.; US2003/229084; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem