Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Recommanded Product: 496-12-8

General procedure: A literature procedure1 was modified by replacing triethylamine with N,N-diisopropylethylamine. To a stirred mixture of tetrahydroisoindoline (0.11 mL, 1.0 mmol), N-Boc-(R)-phenylalanine (265 mg, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (182 mg, 1.0 mmol) and anhydrous 1-hydroxybenzotriazole (203 mg, 1.5 mmol) in N,N-dimethylformamide (3.0 mL) was added N,N-diisopropylethylamine (1.3 mL, 7.5 mmol). The mixture was stirred at 20 for 16 h. The solvent was evaporated and the residue was dissolved in ethyl acetate (20 mL) and the solution was washed with water (2 x 20 mL). The combined aqueous fractions were re-extracted with ethyl acetate (2 x 20 mL) and all the combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2 x 20 mL) then with brine (20 mL) filtered and dried (MgSO4). Column chromatography (25:75 ethyl acetate: dichloromethane) of the residue gave 7c (175 mg, 48%) as a cream solid,

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Isoindoline, and friends who are interested can also refer to it.

Reference:
Article; Chan, A. W. Edith; Greenwood, Simon O. R.; Hansen, D. Flemming; Marson, Charles M.; Bioorganic and medicinal chemistry letters; (2020);,
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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H4ClNO2

General procedure: To a well-stirred solution of isatin and malononitrile(1 mmol each) in ethanol (95percent, 4 mL) was added dimedone,4-hydroxycoumarin, 4-hydroxy-N-methylquinolin-2-one,or 2-methyl-pyrazol-2-one [generated in situ from ethylacetoacetate and hydrazine hydrate, 1 mmol each]. To thissolution was added THAM (30 mol percent) and stirring wascontinued at ambient temperature. Upon completion of thereaction (TLC), water (5 mL) was added and stirring wascontinued for 10 min more. Resultant solid product wasfiltered, washed repeatedly with water, and dried. The dried solid was washed thrice with hexaneechloroformmixture (1:1, v/v) and dried again. Resultant product didnot require any further purification.

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 7477-63-6.

Reference:
Article; Khot, Supriya S.; Anbhule, Prashant V.; Desai, Uday V.; Wadgaonkar, Prakash P.; Comptes Rendus Chimie; vol. 21; 9; (2018); p. 814 – 821;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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-2,4-dihydroxyphenyl)(isoindolin-2-yl)methanone, 7 (PA1): In a 50 mL, three-necked, round-bottomed flask, 5-bromo-2,4-dihydroxybenzoic acid (1.42 g, 5.65 mmol, 1.13 equivalent), l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 1.02 g, 5.25 mmol, 1.05 equivalent) and 1-Hydroxybenzotriazole (HOBT, 776 mg, 5.75 mmol, 1.15 equivalent) were dissolved in dimethylformamide (10 mL) at room temperature. The mixture was stirred at the same temperature for 30 min before isoindoline (596 mg, 5 mmol, 1 equivalent) was added. After 18 h, the reaction mixture was diluted with ethyl acetate (50 mL) and washed sequentially with IN HC1 aqueous solution, saturated aqueous aHC03, and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel; ethyl acetate: hexanes 1 :20 to 1 : 1) to yield PAl (1.17 g, 70% yield). XH NMR (500 MHz, DMSO-d6) delta 10.50 (s, 1H), 10.34 (s, 1H), 7.38-7.36 (m, 2H), 7.34 (s, 1H), 7.29-7.27 (m, 2H), 6.59 (s, 1H), 4.77 (s, 2H), 4.70 (s, 2H); 13C NMR (125 MHz, DMSO-d6) delta 166.6, 155.8, 154.7, 136.9, 131.7, 127.4, 122.9, 117.2, 103.7, 98.6, 52.7 (Rotamers were observed). LRMS (ESI) calculated for [M+H]+ 334.0, found 333.9.

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

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; CHUANG, David, T.; TSO, Shih-Chia; QI, Xiangbing; GUI, Wen-Jun; WU, Cheng-Yang; CHUANG, Jacinta, L.; TAMBAR, Uttam, K.; WYNN, R., Max; WO2015/89360; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., name: N-Vinylphthalimide

b) Ethyl 2-[3-(2-amino-ethyl)-phenoxy]-2-methyl-propionate (13b); 10d (14 g, 49 mmol) is placed in the presence of N-vinylphthalimide (11 g, 63 mmol) and 27 ml (194 mmol) of triethylamine in 160 ml of DMF. Pd(OAc)2 (0.3 g) and P(oTol)3 (0.4 g) are added and the reaction medium is stirred for 10 h at 110 C. The reaction medium is dry concentrated and the residue obtained is taken up in water and extracted with AcOEt. After drying on MgSO4, the organic phases are dry concentrated and the oil isolated is purified by flash chromatography on silica (heptane:AcOEt 90:10). 11.5 g of oil is obtained (62% yield) then placed in a solution of 70 ml of THF and 70 ml of EtOH in the presence of Pd/C under hydrogen at 6 bar. This mixture is stirred for 72 h at ambient temperature. After filtration on celite, the reaction medium is dry concentrated and the residue obtained is purified by flash chromatography on silica (petroleum ether:AcOEt 80:20). 10.9 g of clear oil are obtained (yield=94%). This oil is then placed in 140 ml of EtOH in the presence of 3.5 ml of hydrazine hydrate then this solution is heated at reflux for 4 h. After filtration of the insolubles, the reaction medium is dry concentrated and then the residue obtained is purified by flash chromatography on silica (CH2Cl2:MeOH:NH4OH 90:9:1). 5.7 g of intermediate 13b are thus isolated in the form of an oil (yield=80%). TLC silica gel 60 F 254 Merck, CH2Cl2:MeOH:NH4OH 90:9:1, Rf=0.28.

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; Pierre Fabre Medicament; US2008/167313; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7477-63-6, The chemical industry reduces the impact on the environment during synthesis 7477-63-6, name is 7-Chloroisatin, I believe this compound will play a more active role in future production and life.

General procedure: For compound 3, arenesulfenyl chloride (5 mmol) was added dropwise to a solution of isatin or isatin derivatives (5 mmol) and triethylamine (5 mmol) in N,N-dimethylformamide (DMF, 5 mL) at room temperature. Stirring was continued for an additional 30 min and then the mixture was poured into ice water (20 mL). The yellow precipitates were collected by filtration and recrystallized from ethanol to give pure 3a-3m.

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

Reference:
Article; Shang, Jian-Li; Guo, Hui; Li, Zai-Shun; Ren, Biao; Li, Zheng-Ming; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; Bioorganic and Medicinal Chemistry Letters; vol. 23; 3; (2013); p. 724 – 727;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 603-62-3, name is 3-Nitrophthalimide, A new synthetic method of this compound is introduced below., COA of Formula: C8H4N2O4

Step 1: 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*10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 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) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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; Muller, George; Man, Hon-Wah; Cohen, Benjamin M.; Li, Ying; Xu, Jean; Leong, William W.; US2012/232100; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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 2913-97-5, SDS of cas: 2913-97-5

Example 12d (0.4 g, 0902 mmol) and 2-(l,3-dioxo onidQlm-2- i)acetaldehyde (0.683 g, 3 J61 mmol) were combined in tetral^drof ran (9 J02 mL) under nitrogen , cooled to 0 * C and treated drop-wise with 1M ntaniuin(I V) chloride in die hloro me thane (3 J61 mL, 3.61 mmol) to give an opaque red solution. The sotitionwas stirred for 72 hours at ambient temperature and partitioned b etween ethyl acetate and water. The organic layer was was hed with s aturated aqueous s odium chloride, dried over arLhydrous sodium sulfate, filtered and concentrated. -ificationby chromatography (siEca gel, 0.5-5percent methanol in dichloiomethane) afforded the title confound as a yellow powder (0.45 g, 81percent). NMR (500 MHz, DMS 0-^) 6 1 1.78 ^, ; = 1 S3 Hz, 1 7.93 (d, J = 1 .53 Hz, 1H), 7B1 – 7.85 (m, 4 7.76 (s, l H), 7.24 – 7.30 (m, 1 H), 721 (dd, J = 824, 1.83 Hz, 1H), 7.09 – 7.15 (m, 1H) 699 – 7.05 (m, 1 6.96 (d, J = 2.44 Hz, 1 HI 6.92 (d, J = 824 Hz, 1 HI 5.44 (dd, J = 9.92, 5 4 Hz, 1 HI 4.51 – 4.56 (m, 1H), 4.44 – 4.48 (m, 1 3.87 (dd, J = 13.28, 5.34 Hz, 1 HI 3 J66 (S, 3H), 3 2 (dd, J = 13.28, 10.22 Hz, 1H), 2.98 (s, 3H) . Xi (EpsilonXi 1+) m/z 615 (M+H) 1.

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:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; FIDANZE, Steven D.; LIU, Dachun; MANTEI, Robert A.; MCDANIEL, Keith F.; PRATT, John; SHEPPARD, George S.; WANG, Le; BOGDAN, Andrew; HOLMS, James H.; DIETRICH, Justin D.; MARJANOVIC, Jasmina; HASVOLD, Lisa A.; DAI, Yujia; WO2014/139324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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. Recommanded Product: 3,3-Dimethylindolin-2-one

(d) 3,3-Dimethyl-5-nitroindolin-2-one A solution of 22 ml. fuming nitric acid in 200 ml. 80percent sulphuric acid is added dropwise, with cooling, to a solution of 100 g. (0.62 mol) 3,3-dimethylindolin-2-one in 500 ml. 80percent sulphuric acid. The reaction mixutre is then stirred for about 30 minutes, poured on to ice, filtered with suction, washed with water and dried. Yield: 100 g. (78percent of theory); m.p. 192°-196° C. (ethyl acetate/heptane).

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

Reference:
Patent; Boehringer Mannheim GmbH; US4666923; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 71294-07-0,Some common heterocyclic compound, 71294-07-0, name is 5,6-Difluoroindolin-2-one, molecular formula is C8H5F2NO, 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.

5,6-difluoro-2,3-dihydro-1H-indole Under an argon atmosphere 0.30 g (1.8 mmol) 5,6-difluoro-1,3-dihydro-indol-2-one were dissolved in 10 mL THF and 3.0 mL of a 1 M borane in THF solution were added dropwise. Then the reaction mixture was heated for 2 h to 70 C. and then cooled. After the addition of 3 mL MeOH a further 5 mL of a 4N aqueous hydrochloric acid solution were added and the mixture was refluxed for 1 h. The organic phase was evaporated down, the aqueous phase was washed with DCM and then made alkaline with a 4N aqueous sodium hydroxide solution and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and evaporated down. Yield: 160 mg (47% of theory) ESI-MS: m/z=156 (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 5,6-Difluoroindolin-2-one, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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. Recommanded Product: 102359-00-2

Into a 25-mL round-bottom flask was placed tert-butyl 4-aminopiperidine-1- carboxylate (300 mg, 1.50 mmol, 1.00 equiv), dichloromethane (10 mL), 2-oxo-2,3- dihydro-1H-indole-5-carboxylic acid (319 mg, 1.80 mmol, 1.20 equiv), EDCI (344 mg, 1.79 mmol, 1.20 equiv), and HOBT (304 mg, 2.25 mmol, 1.50 equiv). This was followed by the addition of TEA (454 mg, 4.49 mmol, 3.00 equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 14 h at 20oC. The solids were collected by filtration. This resulted in 393 mg (73%) of tert-butyl 4-(2-oxo-2,3-dihydro-1H-indole-5- amido)piperidine-1-carboxylate as a yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 102359-00-2, its application will become more common.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem