Month: March 2021

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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 3,3-Dimethylindolin-2-one

2c. 3,3-dimethylindoline:; To a 1M of LAH (30 mL) in THF was added 2b (630 mg, 3.88 mmol) in portion. The reaction mixture was stirred at rt for 2 h, then refluxed for 1 h. The reaction mixture was quench with 1 part of H2O (10-mL), one part of 15percent NaOH (5 mL) and another part of H2O (5 mL). The aqueous layer was extracted with EtOAc. The EtOAc layer was dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure to afford 2c (320 mg, 56percent) as an oil. MS (ES) m/z 150 [M+H]+.

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; Bristol-Myers Squibb Company; US2006/293281; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 940054-45-5, name is 4-Chloro-6-fluoroindoline-2,3-dione, molecular formula is C8H3ClFNO2, 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. Quality Control of 4-Chloro-6-fluoroindoline-2,3-dione

Stage 5: 2-amino-6-chloro-4-fluoro-benzoic acid (main isomer) and 2-amino-4-chloro-6-fluoro-benzoic acid (lesser isomer) First sodium hydroxide (10.7 g, 267 mmol) and then 30% hydrogen peroxide (10.7 ml) in water (96 ml) were added to a suspension of the product mixture from stage 4 (8.00 g, 40 mmol) in water (200 ml) at 0 C. The mixture was stirred at room temperature overnight and then brought to pH 3.3 with formic acid (approx. 20 ml, severe foaming). The title compound which had precipitated out was filtered off and dried over phosphorus pentoxide in vacuo. The aqueous solution was extracted with ethyl acetate (2*150 ml). The pH of the aqueous phase was corrected to 3.3 and extraction was carried out again with ethyl acetate (150 ml). The combined organic phases were dried with sodium sulfate and concentrated and the residue was dried in vacuo. Yield: 7.30 g (95%) of the mixture of the regioisomers in the ratio of 9:1, brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 940054-45-5, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; US2008/293749; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6341-92-0, 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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of isatin 2 (0.8 mmol), malononitrile (1.0 mmol) and Ca(OH)2 (0.8 mmol, 59.2 mg) in 5.0 mL of methanol was stirred at roomtemperature for 10 min followed by the addition of chrysin 1(0.5 mmol), which was stirred under reflux for 8 h. After completion ofthe reaction, as indicated by TLC, the mixture was cooled to roomtemperature and then purified by flash chromatography to afford thecorresponding product 3.

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

Reference:
Article; Zhang, Wen-Hui; Chen, Shuang; Liu, Xiong-Li; Feng, Ting-Ting; Yang, Wu-De; Zhou, Ying; Bioorganic and Medicinal Chemistry; vol. 27; 22; (2019);,
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Indoline | C8H9N – PubChem

These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, 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. name: 2-(Bromomethyl)isoindoline-1,3-dione

3.5 g (87 mmol) of sodium hydride are added in portions to a solution of 25 g (87 mmol) of dimethyl2- (4- ert-butoxycarbonylpiperazin-l-yl) malonate in 250 ml of tetrahydrofuran cooled to 2C. The reaction medium is stirred at ambient temperature for 30 minutes, then brought to 2C before dropwise addition of 21 g (87 mmol) of 2- (bromomethyl) isoindole-1, 3-dione in 200 ml of tetrahydrofuran . The reaction medium is stirred at ambient temperature for 20 h, treated by addition of 500 ml of water then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated under vacuum.The crude product obtained is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 27.5 g (73%) of dimethyl 2- (4- ert-butoxycarbonylpiperazin-l-yl) -2- (1, 3-dioxo- 1, 3-dihydro-isoindol-2-ylmethyl) malonate are obtained in the form of a white solid.

The synthetic route of 2-(Bromomethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; CHAMBON, Sandrine; CLARY, Laurence; SCHUPPLI, Marlene; WO2011/33009; (2011); A1;,
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Indoline | C8H9N – PubChem

Synthetic Route of 16800-68-3, 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 16800-68-3 as follows.

3 – (4 – Methoxyphenyl) propyne acid 4 – nitrophenyl-unitz (89.2 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), such as carbene-like (0.015 mmol) 3.96 mg, 1, 8 – diazabicycloundecene -7 – (0.3 mmol 45 mul) and methylene methylene chloride as shown in Formula IV, were 3 ml placed 25 ml in a unitunito-two-port bottle under 30 C inert atmosphere protection, unitunitunitaceous conditions 3h, and mixtures thereof. The reaction solution was concentrated, and eluted, eluting with a mixed 10:1 solvent of petroleum ether: ethyl acetate ratio timetime as eluent column chromatography to collect all the detected eluate fractions, and the solvent was evaporated 27 mg and the solvent was evaporated to obtain the unitz , 55% and beiunit_.

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, category: indolines-derivatives

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 ¡Á3 mL). The DCM layer was combined and washed with brine solution (25 ¡Á 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.

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-Oxoindoline-5-carboxylic Acid, other downstream synthetic routes, hurry up and to see.

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);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 84575-27-9, name is 7-Methoxyindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H7NO3

To 7-methoxy-1 H-indole-2,3-dione (SM-1 b) (500 mg; 2.82 mmol) in DMF (5.0 mL) is added K2C03 (585 mg; 4.23 mmol) in one portion. The reaction mixture is stirred at rt for 30 min before iodomethane (SM-5b) (0.230 mL; 3.67 mmol) is added and stirring is continued at rt for 2 h. The reaction mixture is poured into water, acidified with 4 N HCIaq. and stirred for 30 min. The resulting precipitate is collected by filtration, washed with water and dried in vacuo to give 7-methoxy-1 -methyl-2,3-dihydro-1 H-indole-2,3-dione (A-2a) (HPLC-MS: tRet. = 0.87 min; MS (M+H)+ = 192; method 1 ).

The synthetic route of 84575-27-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; STEURER, Steffen; DAHMANN, Georg; KERRES, Nina; KOEGL, Manfred; (210 pag.)WO2018/108704; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19155-24-9, A common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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 1; 5-amino-1-ethyl-3,3-dimethylindolin-2-one; Compound a (38.4 g), prepared according to the procedures described in Robertson et. al. (J. Med. Chem. 29(10) 1832-1840 (1986)), was dissolved in 300 ml of conc. sulfuric acid using mechanical stirring and cooled using a -40¡ã C. bath until the reaction became very thick. A solution of 10.1 ml of fuming nitric acid and 50 ml of conc. sulfuric acid was added dropwiseover 30 min. The reaction was allowed to warm to ambient temperature with stirring for 12 hours. The reaction mixture was poured into ice water and compound b was collected by filtration and dried (yield: 31 g).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rawson, Thomas E.; Safina, Brian; Dotson, Jennafer; Zhou, Aihe; Aliagas-Martin, Ignacio; Halladay, Jason; Liang, Jun; Rueth, Matthias; Zhu, Bing-Yan; US2007/37791; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.18 (Z)-N-(4-Chlorophenyl)-2-(7-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (3-18) Yield 77percent; m.p.: 251-253 ¡ãC; yellow solid; 1H NMR (DMSO-d6, 400 MHz), delta 12.91 (s, 1H, NNH), 11.35 (s, 1H, NH), 10.86 (s, 1H, SCNH), 7.69-7.63 (m, 3H, J = 6.4 Hz, Ar1-H4, Ar2-H3 and Ar2-H5), 7.51-7.43 (m, 2H, J = 7.6 Hz, Ar2-H2 and Ar2-H6), 7.22 (d, 1H J = 7.6 Hz, Ar1-H6), 7.05 (t, 1H J = 8.0 Hz, Ar1-H5), 2.26 (s, 3H, CH3); 13C NMR (DMSO-d6, 101 MHz), delta 176.3, 163.1, 141.2, 137.4, 132.9, 132.7, 130.0, 128.2, 127.2, 122.3, 120.5, 119.5, 118.1, 15.8; IR: (KBr, nu/cm-1), 3310 (NN-H), 3173 (CON-H), 3057 (Ar-H), 1696 (-CONH-), 1626 (C=N), 1595 and 1539 (Ar-C=C), 1209 (C=S), 1155 (N-N); Elemental analysis calculated for C16H13ClN4OS, C: 55.73, H: 3.80, N: 16.25, found C: 56.01, H: 4.10, N: 16.46; HRMS(MALDI) m/z: calculated. 345.0577, found 345.0565, [M + H]+.

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

Reference:
Article; Zhang, Xu-Meng; Guo, Hui; Li, Zai-Shun; Song, Fu-Hang; Wang, Wei-Min; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 419 – 430;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromoisoindoline-1,3-dione

General procedure: To a solution of NBP (1.5 mmol, 0.339 g) and DBU (1.5 mmol, 0.218 mL) in MeCN (2.0 mL), ethyl phenylphosphinate 1a (1.0 mmol, 0.154 mL) was added. The reaction mixture was stirred at 0 C for 10 min. After the starting material 1a was consumed as indicated by TLC, the reaction mixture was poured into water and then extracted with CH2Cl2 (3 x 10 mL). The combined organic phase was washed with water (3 x 10 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, petroleum ether: ethyl acetate = 3:1) to give 2a (268 mg, 85%) as a white solid.

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 6941-75-9.

Reference:
Article; Li, Yueju; Liang, Fushun; Tetrahedron Letters; vol. 57; 26; (2016); p. 2931 – 2934;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem