Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, 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 13861-75-1, Application In Synthesis of Spiro[cyclopropane-1,3′-indolin]-2′-one

Bromine (0.15 mL, 3.0 mmol) was added drop-wise to a mixture of spiro[cyclopropane-1,3′-[3H]indol]-2′(1’H)-one (486 mg, 3.05 mmol), 174 muL (3.0 mmol) acetic acid (0.174 mL, 3.0 mmol) and sodium acetate (250 mg, 3.0 mmol) in dry dichloromethane (120 mL). After 4 h, the reaction was washed with 5% sodium thiosulfalte and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 5′-bromospiro[cyclopropane-1,3′-indol]-2′(1’H)-one (0.75 g, 100%) as a white solid. This compound was used without further purification.

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; Wyeth; US2006/30615; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

Example 81 3-[4-(2-Diethylaminoethylcarbamoyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic Acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid (80 mg, 0.45 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide to give 210 mg (92%) of the title compound as a yellow orange solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.6 (s, 1H, NH), 7.76 (d, J=8.0 Hz, 1H), 7.66 (s, 1H, H-vinyl), 7.57 (dd, J=1.5 & 8.0 Hz, 1H), 7.40-7.42 (m, 2H), 3.28 (m, 2H, CH2), 2.88 (m, H-piperidine), 2.54 (m, 6H, 3*CH2), 2.44 (s, 3H, CH3), 2.40 (s, 3H, CH3), 1.56 (m, H-piperidine), 0.97 (t, J=6.98 Hz, 6H, N(CH2CH3)2). MS m/z 424 [M+].

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

Reference:
Patent; Pharmacia Corporation; US2003/216410; (2003); 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 2-oxoindoline-6-carboxylate

At room temperature, the 6 – methoxy carbonyl -2 – oxo indoline (50g, 0.26 muM) adding toluene (150 ml) in, slowly adding chloroethyl anhydride (67.5g, 0 . 39 muM). The mixture is heated to reflux, and the stirring reaction 2.5h, then cooling to 80 C, and in the system by adding cyclohexane (100 ml), the resulting solution is cooled to room temperature. Filtering, using toluene and washing the solid, and dried, to obtain white solid 65.8g, yield is 94.2%.

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; Shenyang Pharmaceutical University; Qin Mingze; Gong Ping; Zhang Haotian; Zhao Yanfang; (39 pag.)CN106565682; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-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. Safety of 5-Methylisoindoline-1,3-dione

Example 7: Synthesis of 2-r(4′-chlorobiphenyl-4-yl)(methylsulfonyl)amino1-4-(5-methyl- 1,3 -dioxo- L3-dihydro-2H-isoindol-2-yl)butanoic acid (Compound no. 59) (Scheme III, Path G) Step a: Preparation of prop-2-en-l-yl 2-[(4′-chlorobiphenyl-4- yl)(methylsulfonyl)amino]-4-(5-methyl-l,3-dioxo-l,3-dihydro-2H-isoindol-2- yl)butanoate To a solution of hydroxyl derivative (0.250 g, 0.591 moles) in tetrahydrofuran (10 mL) were added triphenylphosphine (0.232 g, 0.88 moles) and 4-methyl phthalimide (0.104 g, 0.65 moles) at 0C. The reaction mixture was stirred for about 15 minutes and diisopropylazodicarboxylate (0.179 g, 0.0.88moles) was added to it at 0C. The reaction mixture was again stirred for about 2 hours at room temperature. After completion, solvent was evaporated to get a crude product which was purified on silica gel column using 30% ethyl acetate: hexane as eluent to get desired compound. Yield: 0.25 g.

The synthetic route of 5-Methylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; KHERA, Manoj Kumar; PALLE, Venkata P.; SATTIGERI, Viswajanani; SATTIGERI, Jitendra; SONI, Ajay; RAUF, Abdul Rehman Abdul; SIVAKUMAR, R.; REDDY, Ranadheer R.; MUSIB, Arpita; CLIFFE, Ian A.; BHATNAGAR, Pradip Kumar; RAY, Abhijit; SRIVASTAVA, Punit; DASTIDAR, Sunanda Ghosh; WO2012/38944; (2012); 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. 1127-59-9, name is 7-Methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 7-Methylindoline-2,3-dione

General procedure: A mixture of 1H-pyrazol-5-amin (1 mmol), isatin (1 mmol) and enolizable C ? H activated compound (1 mmol) in NDDES (1.5 ml)was stirred under microwave irradiation at 60°C for an appropriate time. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature and cold water was added to the reaction mixture. The precipitated solid was isolated by filtration, washed with water and purified by recrystallization from ethanol.

According to the analysis of related databases, 1127-59-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wei-Hong; Chen, Meng-Nan; Hao, Yi; Jiang, Xin; Zhou, Xiao-Lin; Zhang, Zhan-Hui; Journal of Molecular Liquids; vol. 278; (2019); p. 124 – 129;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7147-90-2, The chemical industry reduces the impact on the environment during synthesis 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of N-arylglycine esters 1 (0.3 mmol) in MeCN(2 mL) were added imides or amides 2 (0.2 mmol) and CuCl(2.0 mg, 0.02 mmol). Then, the reaction mixture was stirred at60 C under air atmosphere until the reaction was completed.Then, the resulting mixture was concentrated under vacuum,and the residue was purified by column chromatography (silicagel, petroleum ether/EtOAc as an eluent) to afford the correspondingproducts 3.(10)

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-Chloroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xiao, Li-Jin; Zhu, Zhi-Qiang; Guo, Dong; Xie, Zong-Bo; Lu, Yue; Le, Zhang-Gao; Synlett; vol. 29; 12; (2018); p. 1659 – 1663;,
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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., Quality Control of 2-Oxoindoline-5-carboxylic Acid

Step 1: Synthesis of 2-oxo-N-[(1R)-1-phenylpropyl]indoline-5-carboxamide A mixture of 2-oxoindoline-5-carboxylic acid (300 mg, 1.69 mmol), (1R)-1-phenylpropan-1-amine (228 mg, 1.88 mmol), HATU (740 mg), 0.16 mL DIPEA in dry DMF (7 mL) was stirred overnight, then concentrated under reduced pressure. The resulting residue was diluted with AcOEt and washed with a saturated aq. solution of K2CO3. The organic layer was dried and concentrated in vacuo. Purification by flash chromatography (Kieselgel, CHCl3:MeOH 15:1) provided intermediate 2-oxo-N-[(1R)-1-phenylpropyl]indoline-5-carboxamide: (340 mg, 68%): NMR (300 MHz, DMSO-d6) delta ppm: 10.59 (s,1H), 8.53 (d,1H), 7.78 (s,1H), 7.76 (d,1H), 7.33 (m,4H), 7.22 (t,1H), 6.85 (d,1H), 4.85 (m,1H), 3.53 (s,2H), 1.79 (m,2H), 0.89 (t,3H); tR: 3.09 min; MS (ESI): m/z (M+H)+ 295; (M+H)-293.

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; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.; Ullrich, Axel; Falcenberg, Mathias; Oerfi, Zoltan; EP2837626; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3891-07-4, These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)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.

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

Related Products of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

6-Nitroindoline (1. 2 MMOL) was dissolved in DCM (8 ML), treated with pyridine (2. 4 MMOL) and cooled to 0C. MESO2CI (1. 3 mmol) was added dropwise and the mixture allowed to stir at room temperature overnight. 0. 5 M HCI solution (10 ML) was added and the mixture extracted twice with DCM (10 ml) and twice with EtOAc (10 ML). The combined organics were washed with brine, dried over NA2SO4 and evaporated. The dried residue was dissolved in MeOH (5 ml) and THF (4 ml). Pd/C (100 mg) was added and the mixture stirred under an atmosphere of hydrogen at room temperature for 5 h. The mixture was filtered through a pad of Celite, which was washed with plenty of MeOH and EtOAc. The filtrate was concentrated in vacuum and the residue dried. The crude 6-amino indoline derivative and 4, 6-dichloropyrimidine (1. 5 MMOL) were dissolved in isopropanol (6 ml) and conc. HCI (0. 4 ml) and the mixture heated to reflux for 2. 5 h. For precipitation of the intermediate product the mixture was stored in the fridge overnight. The precipitate (HCI salt) was filtered, washed with a small quantity of cold isopropanol and dried. The intermediate (0. 17 MMOL), the corresponding phenylboronic acid (0. 2 mmol), Na2CO3 (0. 58 mmol) and Pd (PPh3) 2CI2 (3 mol%) were suspended in a mixture of DME/ETOH/WATER (1. 5 ML/0. 3 ML/0. 2 ML). The mixture was heated in the microwave at 125C for 1200 s. H20 (30 ml) was added and the mixture extracted twice with EtOAc (40 ML). Saturated NH4CI solution (20 ml) was added to the water phase and extracted again twice with EtOAc (40 ml). The combined organics were washed with brine and dried over NA2SO4. After evaporation of the solvent the residue was taken up in DMSO and purified via prep.-HPLC (XTerra Prep. MS C18 5 um, 19 X 150 mm, gradient from water to MeCN over 13 min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Nitroindoline, its application will become more common.

Reference:
Patent; AXXIMA PHARMACEUTICALS AG; WO2005/26129; (2005); 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5,7-Dimethylindoline-2,3-dione

General procedure: In a 25 cm3 round bottom flask, to a mixture of isatin(1 mmol), malononitrile (2 mmol), and cyclohexanone (1 mmol) in 10 cm3 30 % ethanol, DABCO (20 mol%)was added. The reaction mixture was stirred at room temperature for time mentioned in Table 2 until completionof reaction, monitored by TLC. After completion ofreaction, the mixture was cooled and filtered to furnish thedesired product in good yields.

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 39603-24-2.

Reference:
Article; Hegade, Pravin G.; Chinchkar, Sarika D.; Pore, Dattaprasad M.; Monatshefte fur Chemie; vol. 147; 7; (2016); p. 1243 – 1249;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem