Tag: M.W=100-200

Reference of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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.

(E) -N-Benzyl-2-nitro-N- (p-tolyl) ethane- 1,1-diamine (1 milliliter(1 mmol)) and 7-fluoroindoline-2,3-dione (1 mmol) were added, toluene (15 ml) and trifluoroacetic acidUnder stirring, the mixture was heated to 110 C and refluxed for 14 hours. TLC monitoring reaction until the point of complete disappearance of raw materials, the reaction solutionExtraction was performed by adding 50 ml of ethyl acetate and 50 ml of saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous Na2SO4,The dried organic phase was concentrated to dryness under reduced pressure, and then 3 ml of acetone and 4 g of 100-200 mesh siliconStir the plastic, vacuum evaporated to dryness, the sample was separated with a petroleum ether / ethyl acetate = 7: 1 eluent silica gel column dried to obtain redN-Benzyl-8-fluoro-3-nitro-2- (p-tolylamino) quinoline-4-carboxamide (Compound 40) was obtained in 65% yield.

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

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
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Related Products of 39755-95-8, A common heterocyclic compound, 39755-95-8, name is 5-Methoxyisatin, 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.

The combined extracts were dried over anhydrous sodium sulfate and concentrated to give 5.1 g (65% yield) of 5-methoxyisatin as a dark red solid. 5-Methoxyisatin (5.0 g) and 30 mL of hydrazine hydrate were heated to reflex for 15 minutes. The reaction mixture was cooled to room temperature and 50 mL of water was added. The mixture was extracted 3 times with 25 mL of ethyl acetate each time, the organic layers combined, dried over anhydrous sodium sulfate and concentrated to give a yellow solid. The solid was stirred in ethyl acetate and 11 g of insoluble material was removed by vacuum filtration and saved. This material proved to be 2-hydrszinocmbonylmethyl-4-anisidine. The filtrate was concentrated and chromatographed on silica gel eluding with ethyl acetate:hexane (1:1) to give 0.7 g of 5-methoxy-2-oxindole as a yellow solid. The 11 g of 2-hydrazinocarbonylmethyl-4-anisidine was refluxed for 1 hour in 20 mL of 1N sodium hydroxide. The mixture was cooled, acidified to pH 2 with concentrated hydrochloric acid and extracted 3 times with 25 mL of ethyl acetate each time. The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated to give 0.8 g of 5-methoxy-2-oxindole as a yellow solid. The combined yield was 1.5 g or 33%.

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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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. 65826-95-1, name is 5-Methylindoline, A new synthetic method of this compound is introduced below., Product Details of 65826-95-1

250ml four bottle,In a nitrogen atmosphere,Add 0.01mol 3,6-dibromo-9H-carbazole,0.03 mol of compound 5-methyl 2,3-dihydro-1H-indole,0.03mol of sodium tert-butoxide,1¡Á10-4 mol Pd2(dba)3,1¡Á10-4 mol of tri-tert-butylphosphine,150ml toluene, heated at reflux for 24 hours,Sampling point plate, the reaction is complete, natural cooling, filtration, rotary evaporation of the filtrate, silica gel column to obtain intermediate A10, purity 93.50%, yield 63.60%.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Xu Kai; Li Chong; Zhang Xiaoqing; Zhang Zhaochao; (40 pag.)CN107880030; (2018); A;,
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Synthetic Route of 41910-64-9, 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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of 4-chloroindoline (3 g, 19.53 mmol) in H2O (3 mL) was added 2-hydroxyacetonitrile (1.988 mL, 20.51 mmol). The reaction was heated at 105 C for 15 h. The mixturewas diluted with EtOAc and the organic portion washed with H2O, dried over Na2SO4, filtered, andconcentrated. The residue was purified by silica gel column chromatography to give the title compound(3.3 g). LCMS m/z = 192.8 [M+H]+; 1H NMR (400 MHz, CD3OD) delta ppm 3.02 (t, 2H, J = 8.2 Hz), 3.46 (t, 2H, J= 8.2 Hz), 4.28 (s, 2H), 6.60 (d, 1H, J = 2.1 Hz), 6.76 (d, 1H, J = 8.0 Hz), 7.09 (t, 1H, J = 8.0 Hz).

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

Reference:
Article; Ren, Albert; Zhu, Xiuwen; Feichtinger, Konrad; Lehman, Juerg; Kasem, Michelle; Schrader, Thomas O.; Wong, Amy; Dang, Huong; Le, Minh; Frazer, John; Unett, David J.; Grottick, Andrew J.; Whelan, Kevin T.; Morgan, Michael E.; Sage, Carleton R.; Semple, Graeme; Bioorganic and Medicinal Chemistry Letters; vol. 30; 5; (2020);,
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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. 13220-46-7, name is 4-Methylindolin-2-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

5-Bromo-4-methyloxindole and 5,7-Dibromo-4-methyloxindole 4-Methyl-2-oxindole (5 g) in 40 mL of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products. Another 7.26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours. The solid was collected by vacuum filtration, washed with 20 mL of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid. The filtrates from this material were chromatographed as above to give 0.6 g of 5-bromo-4-methyl-2-oxindole and 0.5 g of 5,7-dibromo-4-methyl-2-oxindole.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Reference of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 23 Synthesis of 2-methyl-7-[1,2-dihydro-5-methyl-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (IV-4) Similar procedure as Example 20, 5-methylindolin-2-one 0.41 g (2.8 mmol) and 2-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (S4) 0.5 g (2.6 mmol) were reacted for 13 hours at 80 to 90 C., and 0.39 g (46%) of the titled compound as a yellow solid was obtained. 1H-NMR(500 MHz, DMSO-d6) delta 14.66(s, 1H, -NH-1), 12.03(s, 1H, -COOH), 10.82(s, 1H, -NH-1′), 7.46(s, 1H, H-4′), 6.96(d, 1H, J=7.70 Hz, H-6′), 6.80(d, 1H, J=7.75 Hz, H-7′), 3.10(t, 2H, -CH2-4), 2.93(t, 2H, -CH2-6), 2.53(s, 3H, -CH3-2), 2.32(s, 3H, -CH3-5′), 1.95(m, 2H, -CH2-5); ESI-MS: 323.2 [M+H]+; 321.1 [M-H]-.

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

Reference:
Patent; JIANGSU SIMCERE PHARMACEUTICAL R&D CO., LTD.; US2010/160318; (2010); A1;,
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Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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: C10H7NO2

In a sealed tube under argon atmosphere, were introduced compound 4 (0.39g, 2.0mmol), DMF (5mL), triethylamine (1.2mL, 8mmol), palladium diacetate (22.5mg, 0.1mmol), tri(o-tolyl)-phosphine (61mg, 0.2mmol) and N-vinylphthalimide (0.52g, 3mmol). The mixture was stirred at 110C for 5h and then hydrolyzed. The formed solid was solubilized in CH2Cl2, washed with water and brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was recrystallized from toluene to afford 5 as a brown solid (50% yield); mp 236C; 1H NMR (300MHz, DMSO-d6): delta 9.00 (s, 1H), 8.42 (d, J=15Hz, 1H), 7.92 (d, J=9.0Hz, 1H), 7.83-7.82 (m, 2H), 7.80-7.74 (m, 2H), 7.53 (dd, J=9.0, 2.8Hz, 1H), 7.46 (d, J=2.8Hz, 1H), 6.25 (d, J=15Hz, 1H), 3.88 (s, 3H); 13C NMR (75MHz, CD2Cl2): delta 165.2, 162.2, 159.5, 153.6, 145.1, 132.8, 132.1, 130.2, 126.5, 127.4, 123.7, 123.3, 100.6, 95.8, 55.8.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3485-84-5, its application will become more common.

Reference:
Article; Bolteau, Raphael; Caignard, Daniel H.; Delagrange, Philippe; Descamps, Florian; Ettaoussi, Mohamed; Melnyk, Patricia; Yous, Said; European Journal of Medicinal Chemistry; vol. 189; (2020);,
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Synthetic Route of 199328-10-4, These common heterocyclic compound, 199328-10-4, name is Methyl Oxindole-5-carboxylate, 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.

Step 1: A mixture of compound 1 (200 mg, 1.0 mmol) and HC1 (2.0 M in H20, 5 mL) was heated to 100C for overnight. The mixture was concentrated to get compound 2 (180 mg, 97%) as light yellow solid.

The synthetic route of 199328-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACETYLON PHARMACEUTICALS, INC.; VAN DUZER, John, H.; MAZITSCHEK, Ralph; WO2014/121062; (2014); A1;,
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Related Products of 17630-75-0, 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. 17630-75-0, name is 5-Chloro-2-oxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 1. 5-Chloroindoline-2-thione. To a solution of 5-chloroindolin-2-one (336 mg, 2 mmol) in toluene (12 ml) was added Lawesson’s Reagent (1.2 g, 3 mmol). The mixture was stirred at 105C for 3 hr. The resulting mixture was cooled and concentrated under reduced pressure. The residue was diluted with water (40 mL) and extracted with DCM (40 mL). Combined organic layers were dried over anhydrous Na2S04, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give 5-chloroindoline-2-thione (270 mg, 75% yield) as a white solid. LC-MS: m/z: 184(M+H)+.

The synthetic route of 5-Chloro-2-oxindole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE GENERAL HOSPITAL CORPORATION; ZAHLER, Robert; WESTER, Ronald Thure; BRICKNER, Steven Joseph; WO2014/176258; (2014); A1;,
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Some common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, molecular formula is C8H4ClNO2, 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. Application In Synthesis of 6-Chloroisatin

Weigh6-chloroguanidine0.35g (0.0019mol),5-bromoindole anhydride0.48 g (0.0020 mol) was added to a 100 ml three-necked flask containing magnetons, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h,After the reaction is over, stop heating and wait for cooling.The crude product was obtained as a yellow solid powder by suction filtration.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.drying,Weigh 0.45 g and the yield was 66.2%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6341-92-0, its application will become more common.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
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