Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 19727-83-4, name is 6-Nitroindoline, 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 19727-83-4, name: 6-Nitroindoline

Step A: 6-Nitroindoline (3.0 g, 18.3 mmol) was dissolved in THF (45 mL) and Et3N (3.4 mL, 24.4 mmol) at O0C. Acetyl chloride (1.5 mL, 21 mmol) was added drop wise. The mixture was stirred at room temperature for 30 minutes. The mixture was partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated to yield l-acetyl-6-nitroindoline (3.8 g, 100%) as a yellow solid.

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; PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen; WO2006/19831; (2006); 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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Nitroindolin-2-one

Step-b: tert-butyl 5-nitro-2-oxoindoline-l-carboxylate: Di-tert-butyl dicarbonate (4.63 g, 21.2 mmol) and sodium hydrogen carbonate (10.7 g, 127 mmol) were added to a stirred solution of 5-nitroindoIin-2-one (3.0 g, 14.2 mmol) in THF (150 mL) and the mixture was heated to 60C. After 3h, the reaction mixture was cooled, filtered and the filtrate was concentrated under reduced pressure. The obtained crude was purified by chromatography by using silica gel using a mixture of 10% ethyl acetate/hexane as an eluent to get the desired compound as a white solid as (2.3 g, 51%). 1H-NMR (300 MHz, DMSO-i/6): delta 8.3 (d, 1H), 8.2 (s, 1H), 7.9 (d, 2H), 3.8 (s, 2H), 1.5 (s, 9H).

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; ORION CORPORATION; UJJINAMATADA, Ravi Kotrabasaiah; HOSAHALLI, Subramanya; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; WO2015/92118; (2015); 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. 52351-75-4, name is 6-Methoxyindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

(c) Methyl 4-methoxy-anthranilate One hundred fifty-eight grams (0.89 mol) of 6-methoxy-isatine are suspended in 1300 ml of methanol and mixed with a solution of 54 gm (1.34 mol) of sodium ethoxide in 500 ml of methanol. One hundred eight milliliters (1.07 mol) of 30% hydrogen peroxide are added thereto dropwise, under stirring, and the resulting mixture is stirred for 30 minutes. The contents of the flask are concentrated down to half their volume, mixed with water, and adjusted to a pH of 5 to 6 with glacial acetic acid. After extraction with methylene chloride, the mixture is subjected to suction filtration, kieselguhr being used, and dried with sodium sulfate, and the solvent is distilled off. The residue is recrystallized from petroleum ether/cyclohexane (2:1). M.p: 80-82 C., Yield: 109 gm (67.7% of theory). The following compounds are prepared by analogous procedures:

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 52351-75-4.

Reference:
Patent; Dr. Karl Thomae GmbH; US4518597; (1985); A;,
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. 924304-73-4, name is 4-Chloroisoindoline hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H9Cl2N

Step 3: Synthesis of (2Jff,65>,13a5′,14ai?,16a5rZ)-ethyI 6-(tert-butoxycarbonylamino)-2-(4- chloroisoindoline-2~carbonyloxy)-5,16-dioxo-2,3,5,6,7,8,9,ll,13a,14,14a,15,16,16a- tetradecahydro-lH-cyclopropa(e)pyrrolo[2,l-i][l,7,10joxadiazacyclopentadecine-14a- carboxylate[0472] (2R,6S, 13aS, 14aR, 16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-hydroxy- 5,16-dioxo~2,3,5,6,7,8,9,l l,13a,14,14a,15,16,16a4etradecahydro-1H- cyclopropa(e)pyrrolo[2,l-/][l,7,10]oxadiazacyciopentadecine-14a-carboxylate (0.30 g, 0.61 mmol) in toluene (5 mL) was added lj ‘-carbonyldiimidazole (0.12 g, 0.73 ramol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2-amine (0.53 mL, 3.0 mmol), followed by 4- chloroisoindoline hydrochloride salts (0.15 g, 0.79 mmol). The reaction was stirred at 60 C for 3 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (etaexanerEthyl acetate=l:3) to give (2/?,65,13a5,14aR,16a5’,Z)-ethyI 6-{tert- butoxycarbonylamino)-2-(4-chloroisoindoline-2-carbonyloxy)-5,16-dioxo- 2,3,5,6,7,8,9,11, 13a,14,14a,15,16,16a-tetradecahydro-1H-cyclopropa(phiyrrolo[2,l- /][l,7,10]oxadiazacyclopentadecine-14a-carboxylate as white solid (0.18 g, 86%). MS: Calcd.: 674.3; Found: [M+eta]+ 675.1.

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 924304-73-4.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA, INC.; WO2008/137779; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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. SDS of cas: 39603-24-2

General procedure: To a mixture of isatin(s)/acenaphthoquinone/cyclic ketone(s) (1 mmol) and anthranilamide (1mmol) in ethanol(96%, 2 mL), sulfamic acid (0.2 mmol) was added. Thereaction mixture was stirred at ambient temperature forthe time mentioned in table 2 until completion of reaction,as monitored by TLC. After the completion ofreaction, the precipitated products was just filtered. Theconfirmation of isolated products was done by spectraltechniques such as 1H, 13C NMR, IR and massspectrometry.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mane, Mansing M.; Pore, Dattaprasad M.; Journal of Chemical Sciences; vol. 128; 4; (2016); p. 657 – 662;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

To solution of oxindole (4.43 g, 33.3 mmol) in AcOH (35 mL) was added NIS (9 g, 40.0 mmol) at rt. The mixture was stirred for 1.5 hours at which point water (60 mL) was slowly added dropwise, followed by about 5 mL of EtOAc to solubilize impurities. The solid was filtered, washed with a small amount of EtOAc followed by diethyl ether, to give 5-iodo-oxindole (5.4 g, 62%) as a light pink solid clean by proton NMR in DMSO.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Alam, Muzaffar; Du Bois, Daisy Joe; Hawley, Ronald Charles; Kennedy-Smith, Joshua; Minatti, Ana Elena; Palmer, Wylie Solang; Silva, Tania; Wilhelm, Robert Stephen; US2011/71150; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4.92 g (30 mmol) of 5-nitroindoline is introduced by portions into a 250 ml double-necked flask, under argon atmosphere, containing a suspension of 2.4 g (60 mmol) of NaH (60%) in 60 ml DMF,. The vigorous hydrogen evolution is accompanied by the formation of a red suspension. Agitation is maintained for 30 minutes at 23 C. before the addition, by portions, of 4.74 g (30 mmol) of 3-dimethylaminopropyl chloride hydrochloride. The reaction mixture is agitated and heated at 60 C. during 18 hours. The whole is finally poured into 200 ml of a water/ice mixture. The product is then extracted twice with 100 ml of AcOEt. The organic solution is washed successively with 100 ml of water and 100 ml of brine. After drying over MgSO4 and concentration under vacuum, the evaporation residue is purified by flash chromatography an a silica column (eluent: AcOEt/MeOH 100/0 to 0/100). A dark yellow oil is obtained with a yield of 48%.

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

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6653312; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 40314-06-5, The chemical industry reduces the impact on the environment during synthesis 40314-06-5, name is 5-Methylisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Isolation and analytic data for 13, observed in the crossover study, was obtained by independent preparation using the following procedure. Isovaleryl chloride (65 muL, 0.53 mmol) was added to a mixture of 4-methylphthalimide (200 mg, 1.2 mmol), isobutyraldehyde (108 muL, 1.19 mmol), NaI (170 mg, 1.1 mmol), 4 A MS (100 mg), triethylamine (150 muL, 1.1 mmol), ethyl acetate (1.1 mL), and acetonitrile (1.1 mL) at room temperature and with stirring. After 24 h, the mixture was diluted in EtOAc and washed with 1 M NaOH (3×) and brine. The organic phase was dried (MgSO4) and concentrated. Purification by flash chromatography (SiO2, hexanes:EtOAc 4:1) gave 13 (105 mg, 0.33 mmol, 62%) as a white solid. 1H NMR (300 MHz, CDCl3): delta 7.76 (d, J=7.6Hz, 1H), 7.68 (s, 1H), 7.55 (d, J=7.6Hz, 1H), 6.19 (d, J=10.4Hz, 1H), 2.90 (nfom, 1H), 2.52 (s, 3H), 2.23 (d, J=7.3Hz, 2H), 2.09 (septet, J=6.7Hz, 1H), 1.08 (d, J=6.6Hz, 3H), 0.91 (d, J=6.6Hz, 3H), 0.90 (d, J=7Hz, 3H), and 0.88 (d, J=7.6Hz, 3H). 13C NMR (75 MHz, CDCl3): delta 171.9, 167.1, 166.9, 145.8, 135.0, 131.8, 128.9, 124.2, 123.6, 79.1, 43.1, 29.5, 25.6, 22.3, 22.1, 19.0, and 17.9. IR (neat): 2963, 2875, 1779, 1748, 1721, 1618, 1468, 1430, 1363, 1101, and 1006 cm-1. HRMS (ESI-TOF): Calcd for C18H23NNaO4+ [M+Na+] requires 340.1519; found 340.1522. Mp: 53-55 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, 5-Methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41910-64-9, name is 4-Chloroindoline, 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 41910-64-9, Safety of 4-Chloroindoline

1 , 1 -dime th yleth yl 4-chloro-2, 3-dih ydro- 1 H-indole- 1 -carboxylateA solution of 4-chloro-2,3-dihydro-1 H-indole (4.0 g, 26.0 mmol), Boc20 (6.05 mL, 26.0 mmol), DIEA (9.10 mL, 52.1 mmol), DMAP (0.318 g, 2.60 mmol) was stirred at room temperature overnight. LCMS indicated complete conversion. The reaction mixture was poured into 0.1 N HCI (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to afford 1 ,1 – dimethylethyl 4-chloro-2,3-dihydro-1 H-indole-1 -carboxylate (6.36 g) as a yellow oily semisolid. LC-MS(ES) m/z = 198 [M+H-t-Bu]+. 1H NMR (400 MHz, DMSO-d6) delta ppm 1 .51 (s, 9 H), 3.07 (t, J=8.72 Hz, 2 H), 3.95 (t, J=8.72 Hz, 2 H), 6.98 (d, J=8.84 Hz, 1 H), 7.19 (t, J=8.08 Hz, 1 H), 7.48 – 7.70 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroindoline, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, 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 7147-90-2, Quality Control of 5-Chloroisoindoline-1,3-dione

4- Chlorophthalimide (273 mg) is dissolved in a minimum of boiling ethanol (ca. 2.5 ml). 37% formaldehyde solution (0.15 ml) is added to the still hot solution followed by /V-(4-chlorophenyl)glycine (279 mg). Reflux is continued for 3 h. The yellow solution is kept in the refrigerator overnight. The yellow precipitate is collected by suction filtration, washed with ethanol, and dried in vacuo. The crude is recrystallised from ethanol to provide /V-[(5-chloro-l,3-dioxo-2-isondolinyl)methyl]- /V-(4-chlorophenyl)glycine (135 mg) as light yellow crystals. 1H-NMR (500 MHz, DMSOcI6): delta (ppm) = 4.26 (s, 2H), 5.24 (s, 2H), 6.97 (d, J = 9.1 Hz, 2H), 7.22 (d, J = 9.1 Hz, 2H), 7.90 (d, J = 1.2 Hz, 2H), 7.97 (t, J = 1.2 Hz, IH), 12.71 (br s, IH).13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 51.77 (CH2), 54.72 (CH2), 114.39 (2 CH), 121.70 (C), 123.35 (CH), 124.99 (CH), 128.39 (2 CH), 129.97 (C), 133.41 (C), 134.38 (CH), 139.41 (C), 145.34 (C), 167.01 (CO), 167.35 (CO), 171.48 (CO). MS ( + ESI): m/z = 379 (M + H).

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:
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem