Month: July 2021

Reference of 603-62-3, A common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, 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 preparation of 2-amino-6-nitrobenzoic acid was carried out in accordance with the literature (R. Kahn, Chem. Ber. 1902, 35, 3857-3884; W. S. Saari, J. E. Schwering, J. Heterocycl. Chem. 1986, 23, 1253-1255) via regioselective opening of 3-nitrophthalimide with aqueous potassium hydroxide to give phthalamic acid and subsequent Hofmann degradation with sodium hypobromite to give the 2-amino-6-nitrobenzoic acid.

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

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

Related Products of 15362-40-0, 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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The desired compounds 2(a-d), 3(b-d) and 4(b-d) were procured by subjecting an equivalent mixture of compounds 9 (a-d) (1 mmol) and an active methylene compound- barbituric acid, oxindole and indolinone (1 mmol), respectively in methanol (2 mL) using catalytic amount of piperidine to microwave irradiations at 120 oC for 30 min. The reaction was monitored by TLC after every 10 min. The yellow solid obtained was filtered followed by washing with methanol and dried in air.

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kaur, Manpreet; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 29; 1; (2019); p. 32 – 35;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1127-59-9, The chemical industry reduces the impact on the environment during synthesis 1127-59-9, name is 7-Methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of isatin (0.14 g, 1mmol), 5,5-dimethylcyclohexanedione (0.14 g, 1 mmol), 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one (0.22 g, 1 mmol) and H3PW12O40 (0.06 g, 3 molpercent) in dry acetonitrile (5 ml) was refluxed. The reaction progress was monitored by thin-layer chromatography (eluent: ethylacetate/hexane (2:1)). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with acetonitrile (10ml). The obtained crude mass was purified by column chromatography over silica gel using ethylacetate/hexane (1:1) as eluent to give the desired product.

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

Reference:
Article; Jannati, Saeideh; Esmaeili, Abbas Ali; Tetrahedron; vol. 74; 24; (2018); p. 2967 – 2972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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. SDS of cas: 923590-95-8

Step 4: 1-t-Butyl 2-methyl (2S,4R)-4-(11(4-bromo-1,3-dthydro-2H-isoindol-2-yl)carbonyl]oxy}pyrrolidine-1,2-dicarboicylate To a solution of (2S,4R)-B0C-4-hydroxyproline methyl ester (126.3 g, 515 mmol) in DMF (960 mL) at 0 C. was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at room temperature for 3 h. 4-Bromoisoindoline hydrochloride (120 g, 515 mmol) and diisopropylethylamine (96.3 mL, 540 mmol) were added and the reaction mixture heated to 50 C. for 6 h then allowed to cool to room temperature and stirred overnight The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+14)* ; calcd for C20H20BrN2O6: 471.1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 923590-95-8, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; US2010/160403; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 40314-06-5,Some common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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.

Intermediate 5-1Preparation of 2-(5-bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one Step 1 A mixture of 5-methylisoindoline-1,3-dione (5.00 g, 31.0 mmol) and tin shavings (8.84 g, 74.5 mmol) in acetic acid (30 mL) and concentrated hydrochloric acid (15 mL) was heated at reflux for 3 h. The hot solution was filtered and the residual tin shavings were washed with acetic acid. The filtrate was concentrated and the residue was diluted with DCM (200 mL), and washed with water (20 mL) and brine (20 mL), dried and concentrated. The precipitate which formed during the concentration was collected by filtration and washed with DCM (5 mL) and dried under vacuum to give 5-methylisoindolin-1-one (2.3 g, 50%). 1H NMR (400 MHz, chloroform-d) delta 7.70 (1H, d, J=7.77 Hz), 7.43 (1H, s), 7.35 (1H, d, J=7.77 Hz), 4.46 (2H, s), 2.48 (3H, s). Mass spectrum m/z 148.0 (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-Methylisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/160303; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 181140-34-1, 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compounds 3-7 have been synthesized using a procedure originallyreported by Roehrig et al.16 Chiral amine or amino alcohol(0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

The chemical industry reduces the impact on the environment during synthesis (R)-(-)-N-(2,3-Epoxypropyl)phthalimide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 65435-04-3, 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. 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 9.3 g 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80-90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL of ethanol. The solid was dissolved in 90 mL of 2.5 N sodium hydroxide and stirred at 70-80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.

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-(2-Chloroacetyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 64483-69-8,Some common heterocyclic compound, 64483-69-8, name is 5-Acetylindolin-2-one, molecular formula is C10H9NO2, 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 II 1,5-diacetyl-2-indolinone 48.9 g (0.279 mol) 5-acetyl-2-indolinone are stirred in 400 ml acetic anhydride in an oil bath at 140 C. for 2 h. The starting material dissolves during this time. Then the reaction mixture is left to cool, evaporated down, the precipitate is removed by suction filtering, washed with ether and the product is dried. Yield: 56.0 g (92.4% of theory) Rf=0.41 (silica gel, methylene chloride/methanol 50:1) C12H11NO3 (MW=217.223) Mass spectrum: m/z=216 (M-H)-

The synthetic route of 64483-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209302; (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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, This compound has unique chemical properties. The synthetic route is as follows., name: Potassium 1,3-dioxoisoindolin-2-ide

To a solution of 240 1-(bromomethyl)-4-methylbenzene (5 g, 27 mmol) in 28 DMF (30 mL) was added 242 potassium 1,3-dioxoisoindolin-2-ide (7.51 g, 40.5 mmol). The mixture was stirred at 100 C. for 14 hours. The reaction mixture was concentrated under reduced pressure to remove DMF. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=0 to 20%) to give 243 2-(4-methylbenzyl)isoindoline-1,3-dione (5.50 g, 81% yield). 1H NMR (chloroform-d 400 MHz) delta 7.85 (d, J=3.2 Hz, 2H), 7.84 (d, J=3.2 Hz, 2H), 7.34 (d, J=7.6 Hz, 2H), 7.13 (d, J=8.0 Hz, 2H), 4.82 (s, 2H), 2.32 (s, 3H).

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 1074-82-4.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; (154 pag.)US2019/194189; (2019); 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H9Cl2NO

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem