Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-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 667463-64-1, Recommanded Product: 6-Bromo-1-methylindoline-2,3-dione

Step 2: Synthesis of Intermediate 1-12.2 1-12.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HC1. The organic layer is dried over MgSC>4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001 003.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

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,
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Application of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

This compound was obtained by mixing fuming nitric acid (1.0 mmol) and the precursor compound (0.10 mmol) at – 5 C and stirring for 2 h (Scheme 1). The reaction mixture was poured into a mixture of water and ice. The pH was adjusted to 6 by adding CaCO3. The obtained white solid was vacuum filtered, with yield 93%; Mp 87.1-89.5 C. IR (ATR): 3062, 3030, 2978, 2886, 1774, 1716, 1608, 1422, 1402, 1288, 982, 870, 722, 530. 1H NMR (200 MHz, DMSO-d6): 3.95 (t, 2H), 4.71 (t, 2H), 7.86 (br s,4H). 13C NMR (50 MHz, DMSO-d6): 34.8, 70.8, 123.1, 131.4, 134.4, 167.5. Anal. Calcd. for C10H8N2O5. Calcd. (%): C, 50.85; H, 3.41; N, 11.86. Found (%): C, 51.09; H, 3.32; N, 11.77.

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Godin, Adriana M.; Araujo, Debora P.; Menezes, Raquel R.; Brito, Ana Mercy S.; Melo, Ivo S.F.; Coura, Giovanna M.E.; Soares, Darly G.; Bastos, Leandro F.S.; Amaral, Flavio A.; Ribeiro, Lucas S.; Boff, Daiane; Santos, Julliana R.A.; Santos, Daniel A.; Teixeira, Mauro M.; De Fatima, Angelo; Machado, Renes R.; Coelho, Marcio M.; Pharmacology, Biochemistry and Behavior; vol. 122; (2014); p. 291 – 298;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, 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. Formula: C8H4N2O4

General procedure: A mixture of the appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

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

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3676-85-5, 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 3676-85-5 as follows.

Example 82 N-(2-Chlorobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Diphenylphosphoryl azide (165 mg, 0.60 mmol, 1.2 eq) and triethylamine (61 mg, 0.60 mmol, 1.2 eq) were added to a solution of 2-chlorophenylacetic acid (85 mg, 0.50 mmol) in toluene, and the mixture was stirred at 110C for 60 min. Thereafter, 4-aminophthalimide (81 mg, 0.50 mmol, 1.0 eq) and a minor amount of DMF were added thereto, and the mixture was stirred at 110C for 2 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 (37 mg, 22.6%). MS m/z: 329 1H-NMR delta: 4.40 (2H, d, J = 5.61 Hz), 6.94 (1H, t, J = 5.98 Hz), 7.28 – 7.38 (2H, m), 7.41 (1H, dd, J = 1.71, 7.56 Hz), 7.46 (1H, dd, J = 1.71, 7.56 Hz), 7.61 (1H, dd, J = 1.83, 8.17 Hz), 7.68 (1H, d, J = 8.54 Hz), 8.01 (1H, d, J = 1.46 Hz), 9.42 (1H, s), 11.08 (1H, s)

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

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

Reference of 1677-48-1, 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. 1677-48-1, name is 5,6-Dichloroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1.08 g of 4,5-dichloroindoloquinone and 1.08 g of 5,6-dichloroindole quinone were weighed into a 100 ml three-necked flask, 40 ml of dichloromethane, 0.38 g of sodium borohydride The reaction temperature: 40 , after the end of the reaction, the rotary evaporation to remove the solvent, the crystal to be purple solid 5,6,4 ‘, 5’-tetrachloroindiu red crude 1.03, the reaction time: 4.0h, reaction temperature: 40 , G, yield 51.5%.

The synthetic route of 5,6-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Wang, Culing; Liu, Jianli; Zhao, Danqing; Liu, Zhulan; Zhang, Ning; (10 pag.)CN103980182; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 13861-75-1, The chemical industry reduces the impact on the environment during synthesis 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, I believe this compound will play a more active role in future production and life.

EXAMPLE 6 2′-oxo-N-[(hexahydro-1H-pyrrolizin-7a(5H)-yl)-methyl]spiro[cyclopropane-1,3′-[3’H]indole]1′(2’H)carboxamide, monohydrochloride STR14 To sodium hydride (200 mg, 5.2 mmol, washed 2* with hexane) suspended in THF (5 ml) was added spiro[cyclopropane-1,3′-[3’H]indole]-2′(1’H)-one (207 mg, 1.3 mmol) and the reaction was stirred for 15 minutes. The resulting suspension was added to a solution of 20% phosgene in toluene (5.14 ml, 10.4 mmol) in THF (5 mL) and the reaction was then stirred for 2 hours. The reaction mixture was then filtered through celite and concentrated in vacuo to give a beige solid. To the solid dissolved in THF (5 ml) was added a suspension of 7a-aminomethyl-hexahydro-1H-pyrrolizine (200 mg, 1.4 mmol) [J. Het. Chem. 1987, Vol. 24, 47], triethylamine (197 mul, 1.3 mmol) in THF (2 ml) and stirred 18 hours. Concentration in vacuo gave a solid which was dissolved in chloroform, washed with saturated K 2 CO3 solution, dried over K2 CO3, filtered and concentrated in vacuo to give the crude desired compound as a solid. Purification on silica gel eluding with 10% CH3 OH(NH3)/CHCl3 gave the title compound (160 mg, 39%). The free base (147 mg, 0.450 mmol) was converted to the hydrochloride salt by treatment with methanolic HCl to give 149 mg (91%) as a 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, Spiro[cyclopropane-1,3′-indolin]-2′-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G. D. Searle & Co.; US5399562; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H4FNO2

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 22190-33-6, These common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, 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.

(i) 5-Bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester To a solution of 600 mg 5-Bromo-2,3-dihydro-1H-indole and 37 mg 4-dimethylaminopyridine in 30 ml acetonitrile was slowly added 992 mg di-tert-butyldicarbonate. After 2 h at 50 C the solvent was removed under reduced pressure. The residue was dissolved in 50 mL ethylacetate and washed with water. The organic solvent was dried over MgSO4 and the solvent was removed under reduced pressure. The product was used without further purification. Yield: 712 mg MS (ES+): m/e= 299.

Statistics shows that 5-Bromoindoline is playing an increasingly important role. we look forward to future research findings about 22190-33-6.

Reference:
Patent; Aventis Pharma Deutschland GmbH; EP1571154; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 87-48-9,Some common heterocyclic compound, 87-48-9, name is 5-Bromoindoline-2,3-dione, 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.

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoindoline-2,3-dione, its application will become more common.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

141452-01-9, name is Methyl indoline-5-carboxylate, 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. COA of Formula: C10H11NO2

To NaH (0.15 g, 3.75 mmol, 60% dispersion) at 0 0C, was added 19a (0.3 g, 0.95 mmol) in 5 mL of DMF. The mixture was stirred at 80 0C for 16h. The mixture was poured into a separatory funnel and DCM (50 mL), brine (50 mL) and 0.19M HCl (20 mL) were added. The layers were separated and the aqueous layer was extracted with DCM (3 x 50 mL). The combined extracts were washed with brine (2 x 50 mL), dried, filtered and evaporated. The residue was purified by preparative HPLC to afford 65 mg (25%) of 19b.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; NEUROCRINE BIOSCIENCES, INC.; TRAN, Joe, A.; CHEN, Chen; WO2010/149685; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem