Tag: M.W=100-200

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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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Adding some certain compound to certain chemical reactions, such as: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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 14192-26-8. 14192-26-8

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (3.17 g, 16.6 mmol) and orthobenzoic acid triethyl ester (11.1 g, 49.8 mmol) was suspended in acetic anhydride (15 mL) and toluene (15 mL). the mixture was stirred at 110 C. overnight. After that time, the solvent was removed by evaporation. The residue was triturated with 10 ml petroleum ether, filtered off, and dried at 50 C. under vacuum to give 6 g product. LCMS: m/z=366 (MH)+

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 Methyl 2-oxoindoline-6-carboxylate.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1074-82-4

8.7ml (6 ¡¤ 5 X 102 moles) 1,5-dibromopentane with6 g (3. 2 X 10 2 moles) Phthalimide potassium salt dissolved in 100ml of N, N- dimethylformamide andunder room temperatureit was stirred for 15hours.The solvent was distilled off under reduced pressure, The residue usingn-hexane: ethyl acetate with a volumeratio of 10: 1 eluent to carry out column chromatography, gradually increasingthe polarity to hexane: ethyl acetate with a volume ratio of 5: 1 to give a product of 6.9g(2.3X102 mol) a bromogroup substituted by Phthalimide. The product with 5. 9g (4. 7X 102 mol) of sodium sulfite, 140ml water and 85ml95% ethanol mixed reactionwas heated to 95 C for18h, the remainingsolvent was drained, and the resulting residue was mixed with 73ml ofconcentrated hydrochloric acidthen was heated to 110 C thefor 18H, it was drained, with water – 95% ethanol on the residue to carry out recrystallization to give 5-amino-1-pentylSulfonic acid 2. 7g (total yield 50%).

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, 1074-82-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Institute of Chemistry Chinese Academy of Sciences; zhao, jingquan; DENG, HONG; XEI, JIE; (16 pag.)CN101948412; (2016); B;,
Indoline – Wikipedia,
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A common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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. 324-03-8.

General procedure: The typical process for preparation of isatin-DHEAconjugates 4a-e is shown as following: To a solution of dehydroepiandrosterone-17hydrazone 3 (0.3 g, 1 mmol) inethanol (15 mL) was added the equal amounts of substituted isatin (1 mmol), which werestirred at ambient temperature or 50 oC and detected by thin-layerchromatography. Then the solution was concentrated, and the condensation product 4a-eseparated out on cooling (0-4 oC) and was recrystallized from ethanol. All the compounds were characterized by ESI-MS, 1HNMR spectroscopic data

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

Reference:
Article; Ke, Shaoyong; Shi, Liqiao; Yang, Ziwen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4628 – 4631;,
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222036-66-0, 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. 222036-66-0, name is 5-Aminoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 4: 5-f(2-mS,2SV2-ri-(5-chloropyrimidin-2-vnpiperidin-4- yllcyclorhororhoyl}efoyl)amino1isoindolin- 1 -one2-{(lS,2R)-2-[l-(5-chloropyrimidin-2-yl)piperidin-4-yl]cycIopropyl}ethyl 4- methylbenzenesulfonate from step 1 of Example 5 (100 mg, 0.23 mmol) was dissolved in sulfolane and 5-aminoisoindolin-1-one (68 mg, 0.46 mmol) from step 3 of this example added. The mixture was at stirred 110 ¡ãC for 3 and at 120 ¡ãC for 2 hours.The mixture was cooled to RT, diluted with 4:1 water: saturated sodium bicarbonate (40 ml), extracted with EtOAc (3×30 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered, the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 80percent acetone : hexanes to give the titled compound. LRMS calc: 411.18; obs: 412.08 (M+l).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem