Tag: M.W=100-200

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

a, 2400 ml of tetrahydrofuran was charged into the reaction flask A, and the mixture was cooled to -10 C or less, 750 g of N-hydroxyethyl phthalimide and 345 g of NaH were added successively (while stirring at a low speed, N-hydroxyethyl phthalimide, NaH added to the beginning of the dropwise addition of ethyl 4-chloroacetoacetate time interval within 30min); the reaction flask temperature down to -10 C below, 732 g of ethyl 4-chloroacetoacetate was added slowly dropwise, and the temperature was controlled below 0 C and the addition was completed in 1.5 to 2 hours. The temperature was raised to 28 to 32 C. After 5 to 6 hours of reaction, 1500 ml of toluene was added, The temperature dropped below 5 C to give a toluene dilution of the reaction solution; b, add 1700 ml of toluene, 2800 ml of water and 1178 g of acetic acid to the reaction flask B at a temperature below 5 C; add the toluene dilution of the above reaction solution with 1 to 1.5 h at a temperature below 10 C; After stirring for 10 min, the mixture was allowed to stand for 15 min, and the aqueous layer was removed. The toluene layer was washed 5 times with a mass fraction of 4% brine (2500 ml each). After the washed toluene solution was added anhydrous magnesium sulfate, And the toluene solution was concentrated under reduced pressure to remove toluene (the amount of toluene removed was 2700 ml or more and the toluene content was not more than a predetermined value) to give ethyl-4- (2-phthalimidoethoxy) acetoacetate in a yield of 93%

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

Reference:
Patent; Qianhui Pharmaceutical (Anhui) Co., Ltd.; Yang Huilai; Mao Jie; Sun Xuexi; (7 pag.)CN106749187; (2017); A;,
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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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6341-92-0

General procedure: In the presence of K2CO3 (1mol) and tetrabutylammonium bromide (1mol), isatin or substituted isatin 6a-i (0.5mol) was reacted with BnBr or CH3I (1mol) in DMF (6L) and the reaction mixture was stirred 12h at room temperature. Intermediates 6j-p were obtained by filtration and purified by recrystallization from acetic acid with high yield (72.7%-85.1%).

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hua-Quan; Wang, De-Cai; Wu, Fei; Tang, Wei; Ouyang, Ping-Kai; Chinese Chemical Letters; vol. 24; 10; (2013); p. 929 – 933;,
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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 14192-26-8 as follows. Recommanded Product: Methyl 2-oxoindoline-6-carboxylate

In a 250ml reaction flask was added 28.7g of 2-oxindole-6-carboxylic acid methyl ester, 130ml ethanol, stirred open, then added 16.8ml (17.6g) benzaldehyde, 2.97 mL piperidine was heated to 70 -80C, after 2 hours the reaction was allowed to cool to 20 C- 30C, the precipitate was filtered, the filter cake was washed with ethanol, and dried under vacuum 5 hours 50 deg.] C give a yellow solid 40.2g (IV of), yield: 96.0%.

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Simbos Pharm Co., Ltd; Li, Yong; Hu, wei; Du, Huanda; Wang, wanqing; Liu, YanHua; (8 pag.)CN105461609; (2016); A;,
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Related Products of 480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-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.

Intermediate 6B: [00203] Potassium nitrate (1.215 g, 12.02 mmol) was added portionwise to a solution of Intermediate 6A (1.6 g, 12.02 mmol) in sulfuric acid (24 mL) at 0 0C over 10 min. The reaction mixture was stirred to 3 h at ambient temperature. The reaction mixture was poured onto ice and the resulting precipitate was washed with water and dried in vacuo to yield Intermediate 6B (1.85 g, 10.38 mmol, 86 % yield) as a beige solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 4.53 (s, 2 H) 7.86 (d, J=8.25 Hz, 1 H) 8.33 (s, 1 H) 8.45 (dd, J=8.24, 2.20 Hz, 1 H) 8.97 (s, 1 H). MS (ESI) m/z 179.0 (M+H)+.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, Recommanded Product: 6-Chlorooxindole

General procedure: To a solution of s7 (398 mg, 1.18 mmol) in EtOH (2.30 mL) were successively added addedoxindole (105 mg, 1.13 mmol) and piperidine (12 muL, 0.12 mmol) at room temperature. After 20 h,the reaction mixture was concentrated in vacuo. The residue was purified by columnchromatography (silica gel, hexane/EtOAc = 4/1) to afford aldehyde 1a (422 mg, 84%) as yellowsolid, whose geometry was determined by X-ray crystal analysis.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Machida, Mizuki; Mori, Keiji; Chemistry Letters; vol. 47; 7; (2018); p. 868 – 871;,
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Synthetic Route of 317-20-4, 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.

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
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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

To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C for 3 hrs, and then heated to 30 C for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hr. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) S 7.69 (brs, 1H, NHH), 7.74 (t, J= 8 Hz, 1H, Ar), 7.92 (dd, J= 1, 8 Hz, 1H, Ar), 8.13 (dd, J= 1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH);13C NMR (DMSO-d6) S 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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

Reference:
Patent; CELGENE CORPORATION; TROTTER, Matthew William, Burnell; RISUENO-PEREZ, Alberto; POURDEHNAD, Michael; GANDHI, Anita; HAGNER, Patrick; (85 pag.)WO2017/53555; (2017); A1;,
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Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 20 ml pressure tube were mixed 5-nitroindoline (500 mg, 3.05 mmol) and sodium carbonate (968 mg, 9.14 mmol) at ambient temperature in anhydrous tetrahydrofuran (5 ml). Methyl iodide (0.190 ml, 3.05 mmol) was added. The reaction mixture was stirred and heated for 24 hours at 60 C. the mixture was diluted with ethyl acetate and water, and the layers were separated. The organic layer was washed with brine, dried with Na2S04, filtered, and concentrated. The residue was purified by flash chromatography on a 40 g silica gel column using an AnaLogix IntelliFlash 280 system eluting with a gradient of 10 to 20% ethyl acetate/hexane to provide the title compound. MS (DCI(+)) m/e 179 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; BA-MAUNG, Nwe Y.; CLARK, Richard F.; ERICKSON, Scott A.; FIDANZE, Steve D.; KAWAI, Megumi; MANTEI, Robert A.; SHEPPARD, George S.; SORENSON, Bryan K.; WANG, Gary T.; WO2011/53476; (2011); A1;,
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39755-95-8, name is 5-Methoxyisatin, 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: C9H7NO3

General procedure: To a stirring solution of indolin-2,3-dione (2.0g, 13.6 mmol, 1.0 equiv.) in anhydrous DMF, sodium hydride (60% suspension inparaffin oil, 0.65 g, 16.32 mmol, 1.2 equiv.) was slowly added at 0 oCunder inert atmosphere. After 1 h, benzyl bromide (1.78 mL, 14.96 mmol,1.1 equiv.) or prenyl bromide (1.73 mL, 14.96 mmol,1.1 equiv.) or methyl iodide ( 0.93 g, 14.96, 1.1equiv.) was added dropwise. Reaction mixture was stirred for another hour.Completion of the reaction was monitored by TLC. The reaction mixture was thenquenched with aq. NH4Cl, washed with water, extracted into ethylacetate. The ethyl acetate fraction was dried over anhydrous sodiumsulfate. It was evaporated under vacuumto give a solid compound which was purified by column chromatography on silicagel (60-120 mesh) using ethyl acetate-hexane (3:97) mixture as eluent.

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

Reference:
Article; Gangar, Mukesh; Kashyap, Naresh; Kumar, Kapil; Goyal, Sandeep; Nair, Vipin A.; Tetrahedron Letters; vol. 56; 51; (2015); p. 7074 – 7081;,
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Reference of 102359-00-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Intermediates (7) (140 mg, 1.2 equiv.), PyBOP (1.2 equiv.) and DIPEA (1.5 equiv.) were added toDMF and stirred at room temperature for 20 min. Then, intermediates (4a-d) (1.0 equiv.) was addedand stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture wasquenched with saturated NaCl solution (25 mL). The aqueous phase was extracted with DCM (25 ×3 mL). The DCM layer was combined and washed with brine solution (25 × 3 mL). The organic layerwas dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. Afterconcentration, the crude product was purified by silica gel column chromatograph using a methanolin DCM gradient (DCM: methanol= 60:1-5:1) yielded compounds 8i-l.N-((1-Benzylpiperidin-4-yl)methyl)-2-Oxoindoline-5-carboxamide (8i). 2-Oxoindoline-5-carboxylic acid(140 mg, 0.79 mmol), (1-Benzylpiperidin-4-yl)methanamine (135 mg, 0.66 mmol), PyBOP (412 mg,0.79 mmol), DIPEA(128 mg, 0.99 mmol), DMF (6 mL). White solid, m.p.:155-156 C, yield: 56%, 1HNMR (400 MHz, CD3OD) delta 7.73-7.68 (m, 2H), 7.53-7.42 (m, 5H), 6.91 (d, J = 8.1 Hz, 1H), 4.26 (s, 2H),3.44 (d, J = 12.5 Hz, 2H), 3.31 (s, 1H), 2.98 (t, J = 12.9 Hz, 2H), 1.97 (d, J = 13.6 Hz, 3H), 1.54 (q, J = 13.1,12.1 Hz, 2H). 13C NMR (101 MHz, CD3OD) delta 178.52, 168.90, 146.69, 130.99, 129.80, 129.40, 128.99,127.92, 127.60, 125.95, 123.42, 123.40, 108.97, 60.21, 51.86, 43.82, 42.11, 34.01, 26.82. HRMS (ESI):calcd. For C22H25N3O2 [M + H]+ 364.2020, found 364.2032.

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-5-carboxylic Acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Guo, Yan; Yang, Hongyu; Huang, Zhongwei; Tian, Sen; Li, Qihang; Du, Chenxi; Chen, Tingkai; Liu, Yang; Sun, Haopeng; Liu, Zongliang; Molecules; vol. 25; 3; (2020);,
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