Month: March 2021

Synthetic Route of 50727-04-3, A common heterocyclic compound, 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione, molecular formula is C9H7NO3, 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.

2-nitrobromobenzene (200 mg, 1 mmol), triethylene diamine (224 mg, 2 mmol),4-methoxy-phthalimide (354 mg, 2 mmol), sodium methoxide (108 mg, 2 mmol),Toluene (2 ml) was added to the dry reaction tube and suspended in an 80 C oil bath for 24 h.After cooling the reaction system, 15 ml of water was added and the aqueous phase was extracted three times with 30 ml of ethyl acetate,The organic phases were combined and the solvent was evaporated under reduced pressure to give 369 mg of a pale yellow solid5-methoxy-2- (2- (4- (2-nitrophenyl) 1-piperazinyl) ethyl) isoindole-1,3-dione,The yield was 90%.

The synthetic route of 50727-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yichun University; Zhu Qiming; Chen Mingwei; (20 pag.)CN106317021; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 150544-04-0, The chemical industry reduces the impact on the environment during synthesis 150544-04-0, name is 6-Aminoindolin-2-one, I believe this compound will play a more active role in future production and life.

[00110] To a solution of 6-amino-l ,3-dihydro-indol-2-one (0.15g, 1.0 mmol) and triethylamine (0.30 g, 3.0 mmol) in THF (10 ml) is added l-isocyanato-3-nitro-benzene (0.16 g, 1.0 mmol). The reaction is stirred at room temperature for 1 hour and the precipitate is collected by vacuum filtration and washed with ethanol to give the desired compound as a light yellow solid. LC-MS: 313.1 (MH+).

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

Reference:
Patent; IRM LLC; WO2006/52936; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 611-09-6, 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. 611-09-6 name is 5-Nitroindoline-2,3-dione, 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.

General procedure: The SiO2/g-C3N4 nanocomposite (25 mg) was dispersed in water (3 ml) for 30 min. Indole (2.0 mmol), and isatin (1.0 mmol) were added to the mixture which was stirred for the appropriate time. The progress of the reaction was monitored by thin layer chromatography. After the completion of the reaction, the crude product was extracted with ethyl acetate and dried over anhydrous Na2SO4. Then, the crude product was recrystallized in hot ethanol. The SiO2/g-C3N4 nanocatalyst was recovered from the aqueous layer by centrifuging, washed with EtOH, dried and reused for the next run.

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

Reference:
Article; Allahresani, Ali; Nasseri, Mohammad Ali; Nakhaei, Alireza; Research on Chemical Intermediates; vol. 43; 11; (2017); p. 6367 – 6378;,
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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference 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.

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

Statistics shows that 6-Chloro-5-(2-chloroethyl)indolin-2-one is playing an increasingly important role. we look forward to future research findings about 118289-55-7.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 17702-83-9, These common heterocyclic compound, 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-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.

200 mg (0.484 mmol) of 112 was dissolved in DMF (8 mL). 466 mg (1.43 mmol) of CS2CO3 and 819 mg (2.42 mmol) N-(8-bromooctyl)phthalimide were added and the mixture was sonicated for 1.5 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (CH2Cl2:MeOH:AcOH, 15: 1 :0.5) to give 120 mg (34percent) of 113d. lH NMR (500 MHz, CDC13) delta 8.29 (s, 1H), 7.84 (dd, J= 5.5, 3.1 Hz, 2H), 7.70 (dd, J= 5.5, 3.1 Hz, 2H), 7.28 (s, 1H), 6.87 (s, 1H), 6.29 (br s, 2H), 5.96 (s, 2H), 4.18 (t, J= 7.5 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 1.62- 1.77 (m, 4H), 1.25- 1.36 (m, 8H); MS (ESI) m/z 671.3 [M+H]+.

Statistics shows that 2-(8-Bromooctyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 17702-83-9.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; CHIOSIS, Gabriela; YAN, Pengrong; PATEL, Pallav; PATEL, Hardik J.; TALDONE, Tony; YANG, Chenghua; SUN, Weilin; OCHIANA, Stefan; WO2015/23976; (2015); 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. 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Aminoisoindoline-1,3-dione

Example 109 N-(1,3-Dioxo-2,3-dihydro-1H-5-isoindolyl)-N’-(2,3,6-trifluorobenzyl)urea Diphenylphosphoryl azide (173 mg, 0.63 mmol, 1.2 eq) and triethylamine (64 mg, 0.63 mmol, 1.2 eq) were added to a solution of 2,3,6-trifluorophenylacetic acid (100 mg, 0.53 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (85 mg, 0.53 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 3 hr. After the completion of the reaction, water and ethyl acetate were added thereto, and the precipitated crystal was collected by filtration and was washed with ethyl acetate to give the title compound as a crystal (100 mg, 54.6%). MS m/z: 349 1H-NMR delta: 4.43 (2H, d, J = 5.37 Hz), 6.98 (1H, t, J = 5.86 Hz), 7.11 – 7.18 (1H, m), 7.40 – 7.50 (1H, m), 7.58 (1H, dd, J = 1.83, 8.05 Hz), 7.66 (1H, d, J = 8.05 Hz), 7.98 (1H, d, J = 1.46 Hz), 9.21 (1H, s), 11.08 (1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0,Some common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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.

Step 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A solution of 5-bromoisoindolin-1-one (2.0 g, 9.4 mmol) , N, N-dimethylpyridin-4-amine (0.23 g, 1.9 mmol) and di-tert-butyl dicarbonate (2.47 g, 11.3 mmol) in DMF (20 ml) was stirred at ambient temperature for 2 h. Water (100 mL) was then added and the mixture was extracted with EtOAc (3×30 mL) . The combined organic fractions were washed with brine (3×10 mL) , dried (Na2SO4) , filtered and the solvent evaporated under reduced pressure. The residue was purified by chromatography on SiO2(1-90EtOAc/isohexane) to give tert-butyl 5-bromo-1-oxoisoindoline-2-carboxylate. MS (EI) calc?d for C13H15BrNO3[M+H]+, 312 found, 312.

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3485-84-5, A common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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: In a sealed tube under argon atmosphere, were introducedcompound 4 (4.74 g, 20 mmol), DMF (20 mL), triethylamine(11.16 mL, 80 mmol), palladium diacetate (225 mg, 1 mmol), tri(otolyl)-phosphine (609 mg, 2 mmol) and N-vinylphthalimide (5.20 g,30 mmol). The mixturewas stirred at 110 C for 3 h and hydrolyzed.The formed solid was solubilized in CH2Cl2, washed with water andbrine, dried over MgSO4 and evaporated under reduced pressure.The crude productwas recrystallized from acetonitrile to afford 7 asa white solid (91% yield)

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; Landagaray, Elodie; Ettaoussi, Mohamed; Rami, Marouan; Boutin, Jean A.; Caignard, Daniel-Henri; Delagrange, Philippe; Melnyk, Patricia; Berthelot, Pascal; Yous, Said; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 621 – 631;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem