Tag: M.W=100-200

Reference of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To the suspension of methyl 2-oxoindoline-6-carboxylate 18[16,17] (50 g, 0.261 mol) in isopropyl alcohol (IPA) (350 ml) was added slowly in sodium methoxide powder (33.8 g,0.626 mol) and stirred for about 15 min. Benzoyl chloride (44 g, 0.313 mol) was added and stirred at 5 to 10 C for about 5 h. After completion of the reaction, the reaction mixture was quenched into ice water (700 mL) and acidified with concentrated HCl up topH 2.0-2.5. The reaction mixture was filtered and washed with water (2 100 mL) and the precipitate is dried to obtain crude product that was recrystallized from acetonitrile (28 mL) to obtain methyl-3-(hydroxy(phenyl)methylene)-2-oxoindoline-6-carboxylatepure crystalline solid (32 g) (61%) (HPLC purity >97%). The filtrate was evaporated invacuum to get the unreacted methyl 2-oxoindoline-6-carboxylate. M.p.: 216-223 C; IR (KBr, cm 1): 3178, 1711, 1651; 1H-NMR (400 MHz, DMSO): delta3.80 (s, 3H), 7.17 (s, 1H), 7.28-7.31 (m, 2H), 7.46-7.50 (m, 3H), 7.72 (d, 2H, J 6.0 Hz),9.52 (s, 1H), 11.53 (s, 1H); 13C-NMR (100 MHz, DMSO): delta 22.12, 52.41, 101.13, 111.13,119.23, 123.06, 126.65, 127.06, 128.65, 129.21, 132.26, 134.47, 136.99, 166.58, 172.52, and175.80; HRMS (ESI): m/z calcd. For C17H13NO4: 295.0845. Found: 296.0921 [M]1.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Arava, Veerareddy; Gogireddy, Surendrareddy; Synthetic Communications; vol. 47; 10; (2017); p. 975 – 981;,
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Electric Literature 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.

7-Bromo-5-chloro-2-oxindole 5-Chloro-2-oxindole (16.8 g) and 19.6 g of N-bromosuccinimide were suspended in 140 mL of acetonitrile and refluxed for 3 hours. Thin layer chromatography (silica, ethyl-acetate) at 2 hours of reflux showed 5-chloro-2-oxindole or N-bromosuccinimide (Rf 0.8), product (Rf 0.85) and a second product (Rf 0.9) whose proportions did not change after another hour of reflux. The mixture was cooled to 10 C., the precipitate was collected by vacuum filtration, washed with 25 mL of ethanol and sucked dry for 20 minutes in the funnel to give 14.1 g of wet product (56% yield). The solid was suspended in 200 mL of denatured ethanol and slurry-washed by stirring and refluxing for 10 minutes. The mixture was cooled in an ice bath to 10 C. The solid product was collected by vacuum filtration, washed with 25 mL of ethanol and dried under vacuum at 40 C. to give 12.7 g (51% yield) of 7-bromo-5-chloro-2-oxindole.

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, 5-Chloro-2-oxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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Indoline | C8H9N – PubChem

Related Products of 16800-68-3, A common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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 pent -2 -acetylenic acid 4 – nitrophenyl-unit 65.7 mg (0.3 mmol), was used. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 3h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 27 mg and gave rise 72% to unit_.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
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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 7699-18-5 as follows. Recommanded Product: 7699-18-5

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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Related Products of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

5-Bromo-2-oxindole 2-Oxindole (1.3 g) in 20 mL acetonitrile was cooled to -10 C. and 2.0 g N-bromosuccinimide was slowly added with stirring. The reaction was stirred for 1 hour at -10 C. and 2 hours at 0 C. The precipitate was collected, washed with water and dried to give 1.9 g (90% yield) of the title compound. 2-Oxindole (53.3 g) was suspended in 640 mL acetonitrile and the mixture cooled to 7 C. in an ice bath with mechanical stirring. Solid N-bromosuccinimide (74.8 g) was added in portions over 20 minutes. After about one-third of the N-bromosuccinimide had been added (over 5 minutes), the temperature had increased to 12 C. The addition was halted until the temperature of the mixture had dropped to 10 C. The addition was resumed keeping the temperature below 12 C. After the addition was complete, the mixture was stirred for 1 hour at 10 C. and then for 1 additional hour during which the mixture was allowed to warm to ambient temperature. The precipitate was collected by vacuum filtration, washed with 80 mL of ethanol and sucked dry for 20 minutes in the filtration funnel to give product containing 6.4% of 2-oxindole by HPLC. The solid was suspended in 1440 mL of denatured ethanol and slurry-washed by stirring and refluxing for 5 minutes at which time most of the solid had dissolved. The mixture was cooled in an ice bath to 13 C. The solid product was collected by vacuum filtration, washed with 80 mL of ethanol and dried under vacuum to give 57.7 g (68.0%) of 5-bromo-2-oxindole containing 1.13% 2-oxindole by HPLC. Slurry-washing with 30% less ethanol gave a better yield (88%) but contained more 2-oxindole (1.76%).

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

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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.

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 22190-33-6, 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. 22190-33-6, name is 5-Bromoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of the title A compound, 5-bromo-2, 3-DIHYDRO-1 H-INDOLE (15. 75 g, 79.54 mmol) in 200 mL acetonitrile and 200 mL dichloromethane is treated with DMAP (0.971 g, 7.95 mmol) and di-t-butyl dicarbonate (19.14 g, 87.49 MMOL). The solution is stirred at RT for 16 h. The mixture is diluted with 300 mL dichloromethane and washed twice with 1 N aqueous HCI and once with brine, dried over anhydrous MGS04, and concentrated to afford 5-bromo-2,3- dihydro-indole-1-carboxylic acid tert-butyl ester.

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, 5-Bromoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/65351; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

Preparation of Compound 29, 1-tert-butyl 5-methyl indoline-1,5-dicarboxylate[0044] Di-tert-butyl dicarbonate (0.489 g, 2.24 mmol), followed by triethylamine (0.315 mL, 2.24 mmol) was added to a solution of Compound 28 (0.328 g, 1 .85 mmol) in dry DCM (5.8 mL) and the reaction mixture was stirred at rt for 26 hrs, concentrated. The residue was dissolved in EtOAc and washed with water (1 x), brine (1 x), dried (MgS04), filtered and concentrated. The crude material was recrystallized from hot EtOH to afford the title compound (373 mg, 73%) as a white solid. 1H NMR (500 MHz, CDCI3) delta 7.88 (d, J = 7.6 Hz, 1 H), 7.82-7.79 (m, 1 H), 4.02 (t, J = 8.7 Hz, 2H), 3.88 (s, 3H), 3.14 – 3.09 (m, 2H), 1 .57 (br s, 9H). Note that there also appears to be 2 extremely broad and weak singlets centred at 7.85 and 7.50 ppm which may be the missing aromatic CH. LRMS (ESI+): 178.09 (loss of Boc) and very weak 278.15

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

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (2015); A1;,
Indoline – Wikipedia,
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Related Products of 56341-37-8, 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 56341-37-8 as follows.

6-CHLOROOXINDOLE (2.5 g, 14.9 MMOL) was suspended in 50 ml 4 M aqueous NAOH and the mixture was REFLUXED for 6 hours. The reaction mixture was allowed to cool and the product precipitated and filtered off with suction. The solid was dissolved in water (100 ml) and precipitated with 4 M aqueous HCI at 0C. The solid was then filtered with suction and dried under vacuum to yield 2.0 g (72%) of white crystalline solid. (2-Amino-4-chloro-phenyl)-acetic acid (700 mg, 3.8 MMOL) was then dissolved in 25 ML pyridine and 1-bromo-3-isocyanato-benzene (811 mg, 4.1 MMOL) was added drop-wise and the solution was stirred for 90 minutes. The reaction mixture was diluted with 150 ml ethyl acetate and washed twice with 1 M aqueous HCI. The organic phase was reduced under vacuum and the product recrystallised from ethyl ACETATE/HEPTANE to yield 680 mg of white crystalline solid (47%) (m. p. 195-196C)

According to the analysis of related databases, 56341-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROSEARCH A/S; WO2004/46090; (2004); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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: C8H4ClNO2

General procedure: To a solution of isatin 1 (1 mmol), nitromethane/nitroethane (3 mmol) was added DABCO (5 mol percent). The mixture was stirred at rt this temperature for 1-5 min. The reaction was monitered by TLC. After completion of the reaction, the mixture was extracted with ethyl acetate (3 .x. 5 mL). The combined organic layers were washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography (ethyl acetate/hexanes: 30:70). All novel compounds were characterized by M.P., NMR, Mass and IR spectral data.

The synthetic route of 7-Chloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meshram; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Tetrahedron Letters; vol. 52; 44; (2011); p. 5862 – 5864;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem