Author: tianli

Adding a certain compound to certain chemical reactions, such as: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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 118289-55-7, 118289-55-7

A mixture of 100 g of 5-(2-chloroethyl)-6-chlorooxindole, 95.2 g of 3-(1-piperazinyl)-1,2-benzisothiazole, 92.1 g of sodium carbonate, 6.5 g of sodium iodide, 28 g of tetrabutylammonium bromide and 1000 ml of cyclohexane was refluxed until reaction completion as shown by thin layer chromatography. The reaction mass was cooled to 30 C. and the solid was filtered. 1000 ml of water was added to the wet compound and stirred for 95 minutes. The solid was filtered and washed with 100 ml water. To the wet compound, 1000 ml methanol was added and stirred for 2.5 to 3 hours at room temperature. The compound was filtered and washed with 200 ml of methanol and dried to afford 142.6 g of the title compound.

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-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Venkataraman, Sundaram; Rao, Uppala Venkata Bhaskara; Muvva, Venkateswarlu; Chitta, Vijayawardhan; US2006/89502; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

883-44-3, Adding a certain compound to certain chemical reactions, such as: 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-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 883-44-3.

4-hydroxycoumarin (6.17 mmol, 1.0 g), PPh3 (6.48 mmol, 1.70 g), and 2-(3-hydroxy-propyl)-isoindole-1,3-dione (6.48 mmol, 1.33 g) is disolved in 20 mL THF and is cooled to 0 C. DIAD (6.79 mmol, 1.33 mL) is added dropwise at 0 C. A precipitate is formed immediately and the reaction mixture thickens. The precipitate is filtered, is washed with Et2O and is dried to afford the title compound (1.62 g, 75%). 1H NMR (DMSO-d6, 300 MHz) delta 7.82 (4H, m), 7.61 (2H, m), 7.37 (1H, m), 7.21 (1H, m), 5.83 (1H, s), 4.28 (2H, t, J=5.75 Hz), 3.83 (2H, t, J=6.25 Hz), 2.19 (2H, m); MS (ESI, Pos.) calcd for C20H15NO5 m/z [M+H]=350.1, found 350.1.

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-Hydroxypropyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/54681; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 317-20-4, name is 7-Fluoroisatin, I believe this compound will play a more active role in future production and life. 317-20-4

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

The chemical industry reduces the impact on the environment during synthesis 317-20-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

118-29-6, 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 118-29-6 as follows.

To a stirred solution of 2,3,3,-trimethylindolenine (20 g, 126 mmol) in concentrated sulphuric acid (100 ml) at ambient temperature was added portionwise N-hydroxymethylphthalimide (20 g, 114 mmol). After 70 hours the reaction mixture was poured onto ice and made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered and dried. The product was obtained as a yellow solid (34.84 g, 87%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 118-29-6, and friends who are interested can also refer to it.

Reference:
Patent; Carnegie Mellon University; US2003/224391; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, 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. 3335-98-6

To 10 ml schlenk bottle adding N – phenyl -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material N – phenyl -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product N – phenyl isatin, I – 4, the isolation yield is 66%

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 3335-98-6.

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 1127-59-9, name is 7-Methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life. 1127-59-9

Step 1:7-methyl-1,3-dihydro-indol-2-one5.00 g (31.0 mmol) 7-methyl-1H-indol-2,3-dione in 18.1 mL (372 mmol) hydrazine hydrate were heated to 110¡ã C. for 3 h.Then the reaction mixture was cooled, the precipitate formed was suction filtered and washed with water.The precipitate was suspended in water, acidified with conc. hydrochloric acid and stirred for 10 min.Then the reaction mixture was stirred for a further 30 min in the ice bath, the precipitate was suction filtered, washed with water and dried.Yield: 1.60 g (35percent of theoretical)ESI-MS: m/z=148 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 1127-59-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/59954; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

59-48-3, A common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

EXAMPLE 120 5-Iodo-1,3-dihydro-indol-2-one A solution of 2-indolinone (2.66 g, 20 mmol) in acetic acid (20 ml) was stirred at room temperature in the presence of N-iodosuccinimide (5.4 g, 24 mmol) for 2 hours. H2O (150 ml) was then added. The precipitate was filtered, washed with H2O, and dried. The resulting, solid was refluxed in ethyl acetate (50 ml), cooled to 0 C., filtered, washed with ethylacetate and ether and dried to provide 5-iodo-1,3-dihydro-indol-2-one (3.62 g. 70%) as a beige solid, m.p. 190-192 C. and MS: m/e=259 (M+).

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alanine, Alexander; Buettelmann, Bernd; Neidhart, Marie-Paule H.; Jaeschke, Georg; Pinard, Emmanuel; Wyler, Rene; US2001/47031; (2001); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 52351-75-4, name is 6-Methoxyindoline-2,3-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. 52351-75-4.

A mixture of 6-methoxyisatin (0.18g, 0.001mol) in Anhyd. ethanol (2ml) and thiosemicarbazide(0.1g, 0.0011 mol) in a mixture of water (2 ml) andglacial acetic acid (0.5 ml) was irradiated undermicrowave irradiation at 560W for 5-minutes. Ayellow coloured solid formed during irradiation. Thesolid was filtered, washed well with water andcrystallized from ethanol-DMF furnishing yellowcrystals. Yield 0.247g (95%), m.p. 265OC.[Found :N, 22.68, S, 12.62. C10H10N4O2S requires N, 22.40;S, 12.80%]; IR: 825, 860 (1, 2, 4-trisubstitutedbenzene ring), 1115 (C=S), 1125 & 1370 (C-O-Cstretching), 1620 (C=N), 1700 (C=O), 3200, 3280,3400 (NH, NH2).

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

Reference:
Article; Singh, Ravinder; Oriental Journal of Chemistry; vol. 31; 1; (2015); p. 509 – 513;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, The chemical industry reduces the impact on the environment during synthesis 496-12-8, name is Isoindoline, I believe this compound will play a more active role in future production and life.

Isoindoline (20 mu, 0.18 mmol) was added to a stirred suspension of3- (2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)benzoic acid (20 mg, 0.051 mmol), HATU (25 mg, 0.066 mmol), and DIPEA (50 mu, 0.29 mmol) in DMF (0.5 mL). The reaction was stirred at r.t. overnight. The reaction was then diluted with MeOH and an off-white ppt. formed. The ppt. was collected by filtration, triturated with MeOH, and air dried to afford the title compound (17 mg, 68% yield). ? NMR (500 MHz, DMSO-i?) delta ppm 8.50 (q, J= 4.58 Hz, 1 H) 7.99 – 8.05 (m, 2 H) 7.90 – 7.95 (m, 2 H) 7.85 (dt, J= 6.10, 2.44 Hz, 1 H) 7.77 – 7.81 (m, 1 H) 7.73 – 7.77 (m, 1 H) 7.58 – 7.64 (m, 2 H) 7.36 – 7.45 (m, 3 H) 7.30 – 7.34 (m, 1 H) 7.29 (s, 2 H) 4.91 (s, 2 H) 4.84 (s, 2 H) 2.86 (d, J = 4.88 Hz, 3 H). LC/MS was performed on a Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. LC/MS method: solvent A = 10% CH3CN/90% H2O/0.1% TFA, solvent B = 90% CH3CN/10% H2O/0.1% TFA, start %B = 0, final %B = 100, gradient time = 3 min, stop time = 4 min, flow rate = 4 ml/min, column: Sunfire CI 8 5 muiotaeta 4.6 x 50 mm; HPLC Rt = 2.48 min, (ES+) m/z (MH+) = 491. Analytical HPLC method: solvent A = 5% CH3CN/95% H2O/0.1% TFA, solvent B = 95% CH3CN/5% H2O/0.1% TFA, start %B = 10, final %B = 100, gradient time = 15 min, stop time = 18 min, flow rate = 1 ml/min. Column: Waters Sunfire C-18, 3.5 muiotaeta 4.6 x 150 mm, Rt = 13.81 min, purity = 100%; column: Waters Xbridge Phenyl 3.5 muiotaeta 4.6 x 150 mm, Rt = 13.81 min, purity = 100%.

The chemical industry reduces the impact on the environment during synthesis Isoindoline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YEUNG, Kap-Sun; PARCELLA, Kyle, E.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine, A.; HAN, Ying; HEWAWASAM, Piyasena; KADOW, John, F.; NICKEL, Andrew; WO2011/112191; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, 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. 2058-72-2 name is 5-Bromo-1-methylindoline-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: To a solution of carboxylic acid (1.3 mmol) in dry CH3CN (3 mL), were added the isatin derivative (1.00 mmol), cyclohexyl isocyanide (1.0 mmol), and sufficiently activated 4 A MS (100 mg). The resultant mixture was stirred at 80 C for the appropriate time as specified in Table 3 and was monitored by TLC. After completion of the reaction, for compounds 4a-o, the solvent was removed under reduced pressure and the residue dissolved in dry CH2Cl2. The 4 A MS was recovered by simple filtration and addition of n-hexane to the filtrate yielded the pure solid products. For compound 4o, the solvent was removed under reduced pressure and the residue was washed with dry CH2Cl2. The solid residue was then dissolved in EtOH, the 4 A MS was recovered by simple filtration, and the filtrate crystallized from ethanol to yield the pure product 4o in 60% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Esmaeili, Abbas Ali; Amini Ghalandarabad, Saeid; Jannati, Saeideh; Tetrahedron Letters; vol. 54; 5; (2013); p. 406 – 408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem