Author: tianli

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. 1127-59-9

General procedure: Isatin 1 (3 mmol), malononitrile (3 mmol), 4-hydroxy-6-methylpyridin-2(1H)-one 2 (3 mmol) were refluxed for 60 minin ethanol (5 ml) with sodium acetate (10 molpercent) or in pyridine (without any catalyst). After the reaction was finished, the solid was filtered,washed with ice ethanol and dried to isolate pure products 3. For their characteristics, see Online Supplementary Materials.

The chemical industry reduces the impact on the environment during synthesis 1127-59-9. I believe this compound will play a more active role in future production and life.

Reference:
Article; Elinson, Michail N.; Ryzhkov, Fedor V.; Vereshchagin, Anatoly N.; Zaimovskaya, Tatiana A.; Korolev, Victor A.; Egorov, Mikhail P.; Mendeleev Communications; vol. 26; 5; (2016); p. 399 – 401;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, 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. 1914-02-9

22d. 3,3-dimethyl-1-(3-nitropyridin-2-yl)indoline The product of 22c (200 mg, 1.35 mmol) and 2-fluoro-3-nitropyridine (0.3 mL) were pre-stirred in a conical microwave container. The mixture was heated at 200 C. under microwave with stirring at high absorption for 10 min. The cooled mixture was dissolved in EtOAc, washed with H2O, brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, hexanes/EtOAc) to give pure 22d (220 mg, yield: 60.4%). LC-MS ESI 270 (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 1914-02-9, its application will become more common.

Reference:
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-74-4, 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 2058-74-4 as follows.

A solution of N-methylisatin (322 mg, 2.0 mmol), indole (258 mg, 2.2 mmol), and K 2 CO 3 (138 mg, 1.0 mmol) in aqueous DMF (H 2 O/DMF, 2:1, 5.0 mL) was heated to 50 o C for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one was obtained as a white solid, 340 mg (61%). A solution of 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one (278 mg, 1.0 mmol), 5-methyl-1H-indole (131 mg, 1.0 mmol), and p-TsOH . H 2 O (19 mg, 0.1 mmol) in CH 2 Cl 2 (2.0 mL) was stirred at room temperature for 1 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 2:1), 5,1′-dimethyl-1H,1’H,1”H-[3,3′;3′,3”]terindol-2′-one was obtained as a white solid, 348 mg (89%). To a stirred solution of 5,1′-dimethyl-1H,1’H,1”H-[3,3′;3′,3”]terindol-2′-one (196 mg, 0.5 mmol) in DMF (3.0 mL) was added t-BuOK (125 mg, 1.1 mmol) and iodomethane (158 mg, 1.1 mmol) successively at 0 o C. The reaction mixture was stirred at room temperature for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 3:1), compound 1g was obtained as a white solid, 156 mg (74%). Compound 1h was synthesized similarly, and the spectroscopic data of unknown compounds 1g and 1h are as follows. Compound 1g: 74%; pale yellow solid, mp 202-204 o C; IR (KBr) 1716, 1490, 1469, 1370, 1340 cm -1 ; 1 H NMR (CDCl 3 , 500 MHz) 1gNOMeNNMeMeMe6 delta 2.31 (s, 3H), 3.35 (s, 3H), 3.66 (s, 3H), 3.69 (s, 3H), 6.79 (s, 1H), 6.86 (s, 1H), 6.93 (t, J = 7.5 Hz, 1H), 6.95-7.05 (m, 3H), 7.12 (s, 1H), 7.13-7.19 (m, 2H), 7.21 (d, J = 8.1 Hz, 1H), 7.27 (d, J = 8.1 Hz, 1H), 7.33 (t, J = 7.7 Hz, 1H), 7.43 (d, J = 7.2 Hz, 1H); 13 C NMR (CDCl 3 , 125 MHz) delta 21.6, 26.6, 32.75, 32.77, 52.7, 108.0, 108.9, 109.2, 113.0, 113.7, 118.9, 121.12, 121.13, 121.4, 122.6, 123.2, 125.3, 126.3, 126.5, 127.9, 128.0, 128.8, 128.9, 134.2, 136.2, 137.7, 142.9, 177.8; MALDI-TOF m/z 420 [M+H] + .

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seo, Da Young; Kim, Gieun; Jo, Hwi Yul; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 39; 4; (2018); p. 587 – 590;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 883-44-3

The reaction was carried out with oven dried glassware. DMSO (85 mul, 1.1 mmol) was added to oxalyl chloride solution (0.35 mL 2 M DCM solution with 5 mL dry DCM) at -78 C. The reaction mixture was stirred at -78 C. for 10 min. 2-(3-Hydroxy-propyl)-isoindole-1,3-dione solution (102 mg, 0.5 mmol, in 2 mL DCM) was added drop wise in 2 min. Then triethylamine (0.35 mL, 2.5 mmol) was added drop wise in 2 min. The mixture was stirred for additional 30 minutes at -78 C. and was warmed up to room temperature. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over MgSO4, filtered, and the filtrated was concentrated in vacuo. The crude product was purified by flash chromatography to give 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde.

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, 883-44-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boyce, Rustum S.; Guo, Hongyan; Mendenhall, Kris G.; Walter, Annette O.; Wang, Weibo; Xia, Yia; US2006/84687; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 496-12-8, name is Isoindoline, 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. 496-12-8

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1 H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSOd6) 10.45 (1 H, s), 10.32 (1H1 s), 7.36 (1 H, br.s), 7.35 (1 H, s), 7.28 (3H, br.s), 6.59 (1 H, s), 4.77 (2H, br.s), 4.71 (2H, br.s). MS: [M+H]+ 332/334.

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; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2913-97-5, Name is N-(2-Oxoethyl)phthalimide, 2913-97-5, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

EXAMPLE 6E tert-butyl (2S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3,3-dimethylbutanoate A solution of the product of Example 3E (9.34 g, 49.4 mmol) in methanol (33 mL) was treated with L-tert-leucine tert-butyl ester hydrochloride (10 g, 44.9 mmol), sodium cyanoborohydride (5.6 g, 89.8 mmol), and acetic acid (1.5 ml, 26.2 mmol), stirred at 25¡ã C. for 4 hours, and partitioned between chloroform and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel, eluding with first with 66percent chloroform in hexanes and then with 33percent ethyl acetate in chloroform to give the title compound (10.5 g, 59percent yield).

Statistics shows that N-(2-Oxoethyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 2913-97-5.

Reference:
Patent; DeGoey, David A.; Flentge, Charles A.; Flosi, William J.; Grampovnik, David J.; Kempf, Dale J.; Klein, Larry L.; Yeung, Ming C.; Randolph, John T.; Wang, Xiu C.; Yu, Su; US2005/148623; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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. 4702-13-0.

Commercially available N-phthaloylglycine (32, 200mg, 0.975mmol) was dissolved in SOCl2 (2.84mL) and refluxed for 2h. After evaporation of the solvent under reduced pressure, the obtained white solid was solubilized in THF (1.7mL), and treated with tris(trimethylsilyl)phosphite (978muL, 2.92mmol) at 0C for 15min, and then stirred at room temperature for 15min. Methanol (4mL) was added and the solution was stirred for 1hat room temperature. The solvent was evaporated under vacuum and the white solid was washed three times with a toluene/hexane mixture (1:1) (4mL), washed with Et2O and dried under vacuum, obtaining the intermediate 37. Yield: 337mg (98.5%).

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

Reference:
Article; Savino, Salvatore; Toscano, Annamaria; Purgatorio, Rosa; Profilo, Emanuela; Laghezza, Antonio; Tortorella, Paolo; Angelelli, Mariacristina; Cellamarea, Saverio; Scala, Rosa; Tricarico, Domenico; Thomas Marobbio, Carlo Marya; Perna, Filippo; Vitale, Paola; Agamennone, Mariangela; Dimiccoli, Vincenzo; Tolomeo, Anna; Scilimati, Antonio; European Journal of Medicinal Chemistry; vol. 158; (2018); p. 184 – 200;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

496-12-8, Adding some certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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.

General procedure: Benzyl bromide 3 (1.0 eq), the appropriate nucleophile (1.2 eq), and K2CO3 (1.2 eq) were dissolved in dry DMF (3 mL) under an inert atmosphere. The reaction stirred at room temperature overnight.The reaction mixture was partitioned between 2 M NaOH and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate. Combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum to obtain the product.

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:
Article; Montgomery, Deanna; Anand, Jessica P.; Baber, Mason A.; Twarozynski, Jack J.; Hartman, Joshua G.; Delong, Lennon J.; Traynor, John R.; Mosberg, Henry I.; Molecules; vol. 24; 23; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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. 317-20-4

Add in a 25 mL round bottom flask(E) -N-4-chlorobenzyl) -N- (4-methylbenzyl) -2-nitroethylene-1,1-diamine(1 mmol)And 7-fluoroindoline-2,3-dione (1.1 mmol), toluene (15 ml) and acetic acid (1 mlMole) was heated under magnetic stirring to 110 C for 14 hours. TLC monitoring reaction until the point of complete disappearance of raw materials, the reaction solutionThe mixture was extracted with 50 ml of ethyl acetate and 50 ml of saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfateDry, with petroleum ether / ethyl acetate = 7: 1 eluent silica gel column was dried to give a yellow solidThe product N- (4-chlorobenzyl) -2-(4-chlorobenzylamino) -7-fluoro-3-nitroquinoline-4-carboxamide (compound 30) in 75% yield.

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 317-20-4.

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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 4 3-Amino-6-bromo-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-bromophenylhydrazine hydrochloride (4.0g, 18.1 mmol) with 4-phthalimido-cyclohexanone (4.39g, 18.1 mmol) in refluxing n-butanol for 20 min, followed by cooling, filtration, and evaporation of the filtrate to dryness yielded 3-phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole as an orange solid (7.45g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;; ; Patent; Smithkline Beecham plc; US5827871; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem