Author: Jessica.F

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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9NO3

EXAMPLE 1 Preparation of Ethyl 4-(2-(Phthalimido)Ethoxy)Acetoacetate (Formula V) 300 liters of toluene was taken into a clean and dry reactor and 50 Kg of sodium hydride was added under a nitrogen atmosphere. 50 Kg of [N-{2-hydroxyethyl}] phthalimide was added to the reactor and the resultant reaction mass was subjected to agitation and heating to 57 C. The reaction mass was maintained at 56-57 C. for 30 minutes. Another 50 Kg of [N-{2-hydroxyethyl}] phthalimide was added to the above reaction mass in 18 lots of 2.7 kg each and a further lot of 1.4 kg, at 60 C. Liberation of hydrogen was observed. The reaction mass was maintained at 57 C. until hydrogen gas liberation ceased. A solution of 94 Kg of ethyl 4-chloroacetoacetate in 287 liters of toluene was added to the above reaction mass at 57 C. and maintained at the same temperature for 20 minutes. The reaction mass was then cooled to 30 C. and then further cooled to 17 C. 200 liters of glacial acetic acid was added to the above obtained reaction mass in three equal lots at 17 C. and stirred for 30 minutes. 1000 liters of water was added to the reaction mass and stirred for 20 minutes. The organic layer was separated and the aqueous layer was extracted into 220 liters of toluene. The combined toluene layer was progressed to the next stage.

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

Reference:
Patent; Bolugoddu, Vijayabhaskar; Dahyabhai, Jaydeepkumar Lilakar; Pingili, Ramachandra Reddy; Veeraboina, Madhu Raju; Gade, Srinivas Reddy; Mallepalli, Srinivas Reddy; Amirisetty, Ravindranath Tagore; US2007/260065; (2007); A1;,
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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., name: Isoindoline

General procedure: A mixture of tert-butyl (2-amino-1-(thiophen-3-yl)ethyl)(methyl)carbamate (33) (310 mg, 1.21 mmol) and N,N-diisopropylethylamine (300 muL, 1.73 mmol) in CH2Cl2 (15 mL) was purged with argon and cooled to 0 C. A solution of 4-nitrophenylchloroformate (244 mg, 1.21 mmol) in CH2Cl2 (5 mL) was added, and resulting reaction mixture was stirred at – 70 C for 30 min. After this time, 5-fluoroisoindoline hydrochloride (150 mg, 0.86 mmol) was added, followed by N,N-diisopropylethylamine (450 muL, 2.60 mmol). The resulting mixture was stirred for 20 h at room temperature. A saturated NaHCO3 solution (10 mL) was added, and the resulting suspension was extracted with CH2Cl2 (3 x15 mL). The combined organic extracts were washed with water (30 mL), then with a brine solution (20 mL) and dried over solid anhydrous Na2SO4. After filtration, the volatiles were removed in vacuo, and the residue was purified by flash chromatography using eluent from CH2Cl2 to CH2Cl2/MeOH (1:1), then reverse phase chromatography using eluent from H2O/MeCN (9:1) MeCN, to give tert-butyl (2-(5-fluoroisoindoline-2-carboxamido)-1-(thiophen-3- yl)ethyl)(methyl)carbamate (34) (150 mg, 41% yield). 300 MHz 1H-NMR (CDCl3, ppm): 7.32 (dd, J=5.0, 2.9 Hz, 1H) 7.24-7.14 (m, 2H) 7.05-6.91 (m, 3H) 5.63-5.41 (m, 1H) 5.09- 4.91 (m, 1H) 4.68 (s, 2H) 4.64 (s, 2H) 4.15-3.88 (m, 1H) 3.77-3.57 (m, 1H) 2.56 (s, 3H) 1.45 (s, 9H); ESI-MS (m/z): 420 [M+H]+; melting point: 182-184 C. Isoindoline (500 mg, 4.20 mmol) and tert-butyl (2-amino-1-phenylethyl)(methyl) carbamate (36) were reacted in CH2Cl2 using procedure described for compound (34) to obtain tert-butyl (2-(isoindoline-2-carboxamido)-1-phenylethyl)(methyl)carbamate (37) (1.49 g, 90% yield). 400 MHz 1H-NMR (CDCl3, ppm): 7.41-7.33 (m, 2H) 7.33-7.29 (m, 2H) 7.29- 7.23 (m, 5H) 5.62-5.41 (m, 1H) 5.19-5.00 (m, 1H) 4.71 (s, 4H) 4.19-3.93 (m, 1H) 3.84-3.62 (m, 1H) 2.55 (s, 3H) 1.46 (s, 9H); ESI-MS (m/z): 396 [M+H]+.

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 496-12-8.

Reference:
Patent; MEBIAS DISCOVERY LLC; TOUNGE, Brett A.; BAYOUMY, Shariff; KUO, Lawrence C.; DAX, Scott; (93 pag.)WO2018/45229; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 100510-65-4, A common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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.

b) N-(3,3-Dimethyl-2-oxo-2,3-dihydro-lH-indol-6-yl)-2-methyl-isonicotinamide To a suspension of 2-methylisonicotinic acid (175 mg, 1.28 mmol) in dry toluene (12.8 ml) was added SOCl2 (167 mg, 103 mu, 1.4 mmol) and dry DMF (9.33 mg, 9.89 mu, 128 muetaiotaomicron) under an argon atmosphere. The mixture was heated under reflux for 2 hours and the solvent was evaporated under reduced pressure. The residue was suspended in dry dichloromethane (3.51 ml) and a suspension of 6-amino-3,3-dimethylindolin-2-one (0.15 g, 851 muiotaetaomicron) and DIPEA (330 mg, 446 mu, 2.55 mmol) in dry dichloromethane (5ml) was added portionwise. The suspension was stirred under an argon atmosphere at room temperature for 16 hours, then diluted with dichloromethane, water and 1 M aqueous sodium carbonate solution. The aqueous phase was extracted with dichloromethane. The combined organic layers were washed with 1 M aqueous sodium carbonate solution, dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using dichloromethane/ methanol as eluent. The title compound was obtained as brown solid (99 mg). MS ESI (m z): 296.3 [(M+H)+]. 1H NMR (DMSO-D6, 400 MHz): (ppm) = 10.38 (s, 2H), 8.64-8.62 (m, 1H), 7.71 (m, 1H), 7.64-7.62 (m, 1H), 7.49 (m, 1H), 7.31-7.23 (m, 2H), 2.57 (s, 3H), 1.24 (s, 6H).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 24566-79-8, name is N-(6-Bromohexyl)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 24566-79-8, HPLC of Formula: C14H16BrNO2

To a stirred solution of compound 3-i (6.39 g, 20.3 mol) in DMF (60 mL) was added potassiun:i thioacetaLe (2.78 g, 34.3 mmoi) portion wise and stirred for 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (250 niL) and stirred for I h. The resultant precipitated was filtered, washed with waLer (100 mL) and dried in vacuo to afford 4-i as an of f-whiLe solid(5.8 g, 93.5%). LCMS: 306.20 (MHi).

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; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; SHIRUDE, Pravin S.; (258 pag.)WO2017/6282; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

PREPARATION 11 5-Acetyl-2-oxindole To 95 ml. of carbon disulfide was added 27 g. (0.202 mole) of aluminum chloride, followed by the dropwise addition of a solution of 3 ml. (0.042 mole) of acetyl chloride in 5 ml. of carbon disulfide, with stirring. Stirring was continued for 5 minutes and then 4.4 g. (0.033 mole) of 2-oxindole was added. The resulting mixture was heated under reflux for 4 hours and cooled. The carbon disulfide was removed by decantation and the residue was triturated under water and recovered by filtration. After drying, 3.2 g. of the title compound was obtained, m.p. 225-227 C.

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, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc.; US4658037; (1987); A;,
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. 20870-78-4, name is 5-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromoindolin-2-one

To a solution of 5-Bromo-1,3-dihydro-indol-2-one (318 mg, 1.5 mmol) and Bis(pinacolato)diboron (420 mg, 1,65 mmol) in dioxane (15 mL) was added KOAc (516 mg, 5.25 mmol). The resulting mixture was degassed, treated with [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium methylene choloride complex (62 mg, 0.075 mmol), heated at 90 C. for 12 h and concentrated. The residue was dissolved in CH2Cl2 (100 mL), washed with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel eluding with 30% ethyl acetate/hexanes to afford 320 mg of Example 133a (82%). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.27 (s, 12H) 3.46 (s, 2H) 6.81 (d, J=7.72 Hz, 1H) 7.49 (m, 2H) 10.51 (s, 1H)) MS (ESI) m/z 260.2 (M+H)+, 276.8 (M+NH4)+

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Iyengar, Rajesh R.; Judd, Andrew S.; Zhao, Gang; Kym, Philip R.; Sham, Hing L.; Gu, Yugui; Liu, Gang; Liu, Mei; Zhao, Hongyu; Clark, Richard F.; Frevert, Ernst U.; Cool, Barbara L.; Zhang, Tianyuan; Keyes, Robert F.; Hansen, Todd M.; Xin, Zhili; US2005/38068; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. Computed Properties of C10H9NO2

To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
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 isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 C (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

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

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 883-44-3,Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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 30 5-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(oxalyl-amino)thiophene-3-carboxylic acid; To a stirred mixture at 0 C. of 2-(3-hydroxy-propyl)-isoindole-1,3-dione (0.2 g, 0.97 mmol), 0.7 M sodium bromide (0.70 ml, 0.46 mmol), TEMPO (3.0 mg, 0.02 mmol) in dichloromethane (1 ml) was added dropwise a solution of bleach (2.1 ml, 4.9 mmol) and sodium hydrogen carbonate (117 mg, 1.4 mmol). The mixture was stirred at 0 C. for 2 hours after the addition was finished. The mixture was extracted with ethyl acetate (3*20 ml). The combined organic extracts were washed with 10% sodium thiosulphate (3*10 ml), brine (10 ml), dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was washed with ethyl acetate (2*1 ml) affording after drying 161 mg (81%) of 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde as a solid. 1H NMR (400 MHz, CDCl3) delta 9.82 (s, 1H), 7.85 (dd, 2H, J=5.6, 2.8 Hz), 7.73 (dd, 2H, J =5.6, 2.8 Hz), 4.04 (t, 2H, J=7.2 Hz), 2.89 (t, 2H, J=7.2 Hz).

The synthetic route of 883-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jeppesen, Lone; Andersen, Henrik Sune; Olsen, Ole Hvilsted; Judge, Luke Milburn; Holsworth, Daniel Dale; Bakir, Farid; Axe, Frank Urban; Ge, Yu; US2005/119332; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 112656-95-8, 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. 112656-95-8, name is 7-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

7′-Nitro-spiro[1,3-dioxolan-2,3′-indol]-2′(1’H)-one (1b) was obtained as grey powder with yield 64%, m.p. 207-208 C [Found C 50.78, H 3.55, N 11.79. C10H8N2O5 requires C 50.85, H 3.41, N 11.86%]; numax (KBr) 1119, 1322, 1346, 1465, 1528, 1630, 1762, 3219 cm-1; deltaH (400.1 MHz, DMSO-d6) 4.30-4.40 (4H, m, -O-(CH2)2-O-), 7.24 (1H, dd, J 7.2, 8.6, -CH-CH-CH-C-); 7.77 (1H, dd, J 0.6, 7.2, -CH-CH-CH-C-), 8.12 (1H, dd, J 1.0, 8.6, -CH-CH-CH-C-), 11.17 (1H, s, NH); deltaC (100.6 MHz, DMSO-d6) 66.4, 123.3, 126.9, 131.6; MS (EI, 70 eV): m/z (I, %): 236 (41, M+), 219 (96), 208 (46), 191 (100), 175 (22), 161 (20), 147 (29), 131 (11), 117 (58), 106 (12), 90 (29), 75 (26), 63 (30), 43 (19), 30 (60).

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-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zaryanova, Ekaterina V.; Ignatov, Alexander A.; Lozynskaya, Nataly A.; Tetrahedron; vol. 73; 49; (2017); p. 6887 – 6893;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem